We’ve done a lottt of city guides on The Everygirl — but we’ve got to play favorites when it comes to one in particular. Our beloved Chicago is home to the Everygirl — and to deep dish pizza, hilarious stand-up comedians, the best freshwater beaches in America, and the nicest people you’ll ever meet.
Chicago is an AMAZING spot for a weekend trip because it’s the perfect blend of relaxed beach attitude and metropolitan hotspot. Spend a warm day playing beach volleyball, followed by a brewery tour and a night at a jazz club. Spend a winter day ice skating and window shopping, then cap it off with a musical and dinner on the 95th floor. The opportunities are endless, and there’s ALWAYS something new to see and explore.
It seems nearly impossible to fit all that we love about Chicago into one tiny weekend — but after years of experimenting and experiencing, we’re finally ready to show you every single thing we want you to try out in our hometown.
Here’s how we’ve broken it down for you:
WHERE TO STAY:
Budget Hotels (less than $150/night)
Mid-range Hotels ($150-300 night)
Treat Yo’self Hotels ($300-500 night)
WHAT TO DO:
WHERE TO EAT:
Best Eats Under $10
Best Dinner Spots
Best Brunch Spots
Drinks with the Girls
Where to Stay
Budget Hotels (under $150/night)
The Publishing House B&B — West Loop
This adorable bed & breakfast/boutique hybrid hotel is home to some of the chicest decor and warmest hospitality around — and one of the best breakfasts that Chicago has to offer. Located in one of the hippest and most popular neighborhoods in town, but tucked away from the hustle and bustle of the downtown Loop, The Publishing House is in an ideal location for anyone who wants to see the sights and hit the town but also relax and unwind.
Freehand Chicago — River North
The Freehand, while not exclusive to Chicago, is an awesome option for groups — you can choose to stay in private rooms or just rent a bed or two. Friend groups can choose rooms with four single beds and a sitting area — making this a perfect, super budget-friendly option for bachelorette weekends or girls’ trips! It’s conveniently located just off the Magnificent Mile and close to the lake — if you’re not bringing a car or are feeling comfortable with public transportation, this is a great option!
Hotel Lincoln — Lincoln Park
Located in Chicago’s adorable and friendly Lincoln Park neighborhood, the Hotel Lincoln boasts one of the best locations in Chicago. Home to one of the best rooftop bars in the city (The J. Parker — see more below) and right across the street from Lincoln Park and its famous (free!) zoo, it’s a great location for anyone who wants to stay off the beaten path of the city but still wants to live it up a little. (This hotel is across the street from my former apartment building — the neighborhood is highly walkable and is home to some GORGEOUS homes!)
Mid-range Hotels ($150-300/night)
The Robey — Wicker Park
Located in Chicago’s suuuper hip Wicker Park neighborhood, this hotel features a large event space, some great eating spots, and best of all, a gorgeous rooftop pool. It’s the tallest building in the neighborhood, so the views up there truly cannot be beat — and it’s also directly next to a couple of bus stops AND an L stop that can take you right downtown. It’s next to some really fun bars, so this is a perfect option for anyone looking to turn up (Wicker Park is known for being quirky, crazy, and unique — it’s where I live currently!)
LondonHouse Chicago — Magnificent Mile
Home to one of the chicest rooftop bars in the city (I’m going to say that a lot… there are SO many good rooftop options — see more below!), LondonHouse is a great place if you want to stay right in the middle of the action. It’s across from the river and is just steps away from the Mag Mile, so it’s a perfect option for a girls’ weekend full of sipping rosé and shopping!
Chicago Athletic Association Hotel — Magnificent Mile
The Chicago Athletic Association Hotel is a MUST-STOP even if you aren’t staying there — but to stay there would mean you’re THIS CLOSE to all the good stuff. Not only is there a Shake Shack on the ground floor, a gorgeous event space and bar on the next floor, and the ultimate rooftop bar (keep reading… I’ll go into detail later!) on the top, but it’s also an ideal location for everything outside the building. It’s right across from Millennium Park (again, keep reading!) and features views of the lake… what else is there!? (Future husband — if you’re reading this, this is where I’d like to have our wedding. Take note!)
Hotel Zachary — Wrigleyville
If you’re in town for a Cubs game (or just to explore all that the north side has to offer), the new Hotel Zachary can’t be beat. It’s a vision of luxury in one of Chicago’s most relaxed neighborhoods — a juxtaposition not lost on the super-chill-but-super-fun-loving residents of Chicago’s Wrigleyville neighborhood. Not only is it LITERALLY across the street from Wrigley Field, but it’s next to Wrigleyville’s super fun row of rowdy sports bars and delicious late-night eats.
Ace Hotel Chicago — West Loop
The Ace Hotel is a super fun boutique hotel located just a stone’s throw away from some of the biggest headquarters in the city (Google, McDonald’s, The Everygirl… wink wink). Not only is it a great place to stay, but it’s also a great place to visit — they have a tasty downstairs restaurant/bar/coffee shop (sometimes our team likes to work from there on work-from-home days!) with outdoor fire pits, AND a fun indoor/outdoor rooftop bar with great drink specials and an even better view of the city.
Thompson Chicago — Gold Coast
This stylish loft-style Gold Coast boutique hotel is one-of-a-kind — it’ll give you downtown vibes with the comfort of an at-home feel. It’s located just off Michigan Avenue near some of the best shopping and sight-seeing Chicago has to offer, and also plays host to the famed Nico Osteria, a breakfast, lunch, and dinner spot serving Italian seafood. Delicious food, great atmosphere, perfect location, and a price that won’t break the bank — score!
Soho House — West Loop
Contrary to popular belief, you don’t have to be a Soho House member to stay at the Chicago outpost of this luxury chain. Not only are the rooms STUNNING and full of amenities, but guests also have full access to the House’s restaurants, rooftop pool, spa, and screening room. Rooms are shockingly affordable considering the amount of access a stay here affords you — if you’re looking for lots to do without leaving the building, this is the spot.
The Hoxton — West Loop
As the newest hotel on this list, The Hoxton Chicago is a fun place to stay if you want a fresh and unique experience. Located just steps away from the new The Wing Chicago, it’s a perfect place to stay if you’re coming for work but want a side of fun. The Hoxton is located in the same neighborhood as Soho House and the Ace Hotel — but this one’s set apart as larger and a little less quirky.
Splurge Hotels ($300-$500/night)
The Peninsula — River North
The Peninsula is the heeeight of luxury. It houses arguably the most popular spa in the city — so if you want some major relaxation on your stay, this is the spot. Bonus: go in the winter and you can skate on their rooftop ice skating rink with a view of Michigan Avenue below you!
The Langham Chicago — River North
According to TripAdvisor, The Langham is the #1 luxury hotel in AMERICA — not just Chicago. Want to get a little crazy? Upgrade to Club status, which features butler service, access to exclusive dining spaces, and more. If you want to spare no expense on views and service, this is the spot.
Ambassador Hotel — Gold Coast
The Ambassador Hotel offers large, airy rooms and a variety of fun daytime and nightlife food and drink options. Whether you’re wine tasting fireside at The Library or eating pasta at Booth One, your taste buds will be SO happy to spend some time here — and the gorgeous decor and views upstairs won’t disappoint either!
Things to Do
See live music
There are SO many truly amazing venues in Chicago to take in live music, and they all have something unique and special to offer. If you’re looking for a buy-tickets-get-hyped, traditional sort of concert-y show, make sure to grab your tickets before you arrive because things sell out faster than I can eat a slice of Pequod’s finest. I cannot recommend the ambiance of Thalia Hall enough (plus the restaurant has a Michelin star, I mean COME ON), but Lincoln Hall and Schubas are also amazing bets. If you’re looking for more spontaneous “let’s go catch some music” vibes, there are tons of really cool dive-y bars that have live music — and you truly cannot go wrong with the iconic Green Mill Tavern, which is where I’d like to spend my last day on earth. Go for the jazz, stay for the cocktails and the ambiance and okay, yes, also the jazz.
You may have heard rumors that Chicago is THE town for up-and-coming comedy talent… and the rumors are true. Second City is one of the most well-recognized improv-based sketch theaters in America — and with good reason. Catch one of their nighttime or brunchtime shows — if it’s good enough for Tina Fey, Amy Poehler, Keegan-Michael Key, and Chris Farley, it’s good enough for us. (P.S. There are TONS of great comedy clubs in Chicago… notable other favorites are the iO Theater and Laugh Factory.)
Ever heard of The Bean? It’s that massive, mirrored, bean-shaped structure in every picture of Chicago — and it’s one of the most popular tourist destinations in the city. It sits in Millennium Park, which is home to other structural wonders and fun sights to walk through. While it’s a cool spot to see, the real magic happens in the summer — when the MP pavilion plays popular movies on weeknights to crowds of wine-drinking picnic-goers. It’s one of our favorite summertime activities in the city (more on that below).
Attend a Chicago game
Chicago is home to so many amazing sports teams — no matter what season you visit in, there’s a game to catch. Sit outside to take in the Cubs, White Sox, or Bears, or head to the Madhouse on Madison for a Blackhawks or Bulls game.
Calling all true-crime lovers — Chicago’s got just the thing for you. Back in the day, Chicago was home to some of the biggest and craziest true-life horror stories in the world (H.H. Holmes and Chicago World’s Fair come to mind). This tour takes you to see points of interest in a variety of different real-life mysteries and murders (example: the above photo shows a stop on the tour, where legendary outlaw and original Public Enemy #1 John Dillinger was assassinated by the FBI). For more insider dish on Chicago’s seedier history, a crime/mob/gangster tour is just the thing. My parents went on a Prohibition Tour when they were here once, and it involved old sites that used to be speakeasies, complete with themed cocktails and period-specific music.
There are SO many breweries located right here in Chicago (Goose Island, Lagunitas, etc.) — and so many of them offer tours of their facilities (and a complimentary drink). There are too many to choose from, so take a look at a list of the best of the best and choose which vibe and location best suits your crew.
The Siskel Film Center is a movie theater like you’ve never seen before — while it’s in a pretty centralized location, it shows movies that you might not get to see otherwise. It’s a completely non-commercialized cinematic experience, perfect for the artistic film-lovers among us.
For a taste of the refined life, taking in a show at the Lyric Opera is a must. Not only are the costumes, scenery, and music insanely impressive, artistic, and make-you-cry beautiful, but going to the historic Lyric Opera House will feel like a fancy night out and a visit back in time. Whether you’re new to opera or a longtime fan, the Lyric Opera in Chicago is only best of the best — where you can catch the best vocalists of the world, or the perfect place to experience an iconic opera for the very first time.
Chicago’s theatre district is home to Broadway in Chicago (an ever-changing array of both touring and long-standing musicals like Hamilton, Wicked, Jersey Boys, Anastasia, and more — check their schedule to see what’s playing while you’re in town), as well as a vibrant variety of other popular non-musical shows (I once saw The Curious Incident of the Dog in the Nighttime). Off the beaten theatre track you’ll find many more options, such as The Lookingglass Theatre on Michigan Avenue, Steppenwolf Theatre in Lincoln Park, and Navy Pier’s Shakespeare Theatre.
I’ll be honest — I don’t love aquariums (fish freak me out!), but there’s no denying that the Shedd Aquarium is one of the coolest ways to spend an indoor day in the city (especially if you have kids with you). Hot tip: The lines are ALWAYS long, so buy your tickets online ahead of time to avoid.
The Museum of Science & Industry is SUPER interactive — there’s a flight simulator that allows you to “fly” different aircrafts from history, and a series that explores the most popular conspiracy theories of all time. For anyone who likes to learn a little something on a trip (and stay on your feet!), this is the move.
The Adler is America’s first ever planetarium — so you can bet your bottom dollar that Chicagoans are proud of it. First of all, it’s on a cool little outlet into the lake at the city’s Museum Campus (where you can find the Shedd, the MSI, and the Field Museum too) — so even if you just admire the building from the outside, it’s a great view of the water. Second of all, though, the planetarium itself is super interesting. Long weekend tip: one Thursday a month, they host Adler After Dark, a 21+ night of dancing, drinking, and exploring the museum. So much fun!
While some would say Chicago’s greatest contribution is the Chicago-style hot dog, the Art Institute is truly a world-renowned treasure, visited by tourists and art-lovers from all over the globe. Voted by TripAdvisor as the #1 best museum in the world a couple years ago, the Institute boasts a lot of bragging rights and has the collections to back it up. Roam the bright, aesthetically-pleasing halls to check out the infamous “The Bedroom” by Van Gogh, the gorgeous Stack of Wheat Series by Monet, or the groundbreaking and spine-chilling instillations in the Modern Wing if that’s more your thing. Whatever your artistic preference, take a break from your sight-seeing and restaurant-hopping to experience the artistic beauty of dozens of time periods and places all over the world. One afternoon at the Art Institute, and you’ll know why it still tops the charts as one of the best museums in the world.
Are you or your crew history buffs? (Yes, being really into Indiana Jones counts!) Don’t miss out on the Field Museum’s amazing and vast display of artifacts. Whether you’re more into Ancient Egypt (there’s a reconstructed three-story Egyptian tomb and interactive representations of life on the Nile) or Restoring the Earth (learn more about sustainability with hands-on activities), don’t leave without checking out famous Sue the Dinosour — though I doubt you would, as the ginormous dinosaur skeleton is pretty hard to miss.
Walk/Bike along the lakefront
Chicago’s entire eastern coast sits on Lake Michigan, arguably the most underrated body of water in the world. As one of America’s largest freshwater lakes, Lake Michigan offers you the water sports and beauty of an ocean with the comfort and safety of a lake (no salt, no sharks, no worries!). Not only are there gorgeous beaches to sit on or explore (I’ll get there), but there are miles of walking/biking paths all along the shore. Divvy bikes are available for rental at hundreds of locations around the city — so you can rent one on the southern shore by the museum campus, then ride along the lake for a few miles and drop your bike off up on the north side. Not much of a biker? The paths are also great for a leisurely (and scenic!) stroll. Going for runs along the lake is one of my all-time favorite ways to break to a sweat — and the combo of lake views and skyline is one in a million. (Just want the view without the walk? Get dropped off at North Avenue Beach, walk along the sidewalk, and look south — it’s honestly breathtaking.)
Zoos are cool and all… but to be in a zoo while ALSO in the middle of a huge city? That’s even better. The Lincoln Park Zoo is centrally located, packed with interesting animals, and is — wait for it — FREE. Since it’s free, you don’t have to feel like you need to pack a full day of animal-visiting into your schedule. Grab a coffee at Elaine’s Coffee Call on the bottom floor of the Lincoln Hotel, drink it while strolling through the zoo for an hour or two, then cross the street to RJ Grunt’s for a boozy milkshake and burger.
North Avenue Beach
If a day of sun, sand, and swimming sounds right up your alley, a summer afternoon at North Avenue beach will be a dream come true. While often super crowded, North Ave. is a fun spot for lounging, sports (there are tons of volleyball nets), and water activities (you can rent paddleboards and jetskis right there on the beach!). You can’t bring alcohol to the beach, but there are a few (kind of crazy) beach clubs that will serve you food and drink.
Chicago Architecture Boat Tour
While it honestly may sound boring, the architecture boat tour is truly anything but. Hop onboard one of the city’s many tour boats, then allow a guide to teach you the fun history of the many gorgeous buildings Chicago has to boast. Not only will you get the best views of the city, but it’s a fun activity to with a date or with a group. (Note: a lot of different tour companies do these tours — I’ve used Wendella!)
For those who want the same amaaaazing views seen on the architecture tour but want to get a bit more active, rentable kayaks on the river are the perfect option. Choose to rent for either daytime or nighttime views (both are great!), and have a little adventure throughout the city. It’s a unique way to get around and see the sights, and it doesn’t hurt to get a little exercise!
One of my absolute favorite summer activities is Millennium Park’s Summer Film Series — every Tuesday night from June to August, the Jay Pritzker Pavilion is transformed into the city’s largest outdoor movie theater, and the grass facing the stage is packed full of picnics, first dates, and girls’ wine nights. Bring a blanket, snacks, and a bottle of rosé — it’s a free, relaxing way to see a new movie and enjoy Chicago’s community.
If you want to see the city without busting your butt by walking miles and miles, a Segway tour is a fun (and funny, Instagram-worthy) way to see the sights. Several companies offer a variety of tours (ranging from nighttime skyline to daytime waterfront), so book online to ensure you’re seeing exactly what you want.
The Maggie Daley Ribbon is a unique ice skating experience because it’s not a typical “rink” — instead, it’s a longer pathway through Maggie Daley Park, which offers lots to see. To skate here is free, but skate rental is a few dollars — well worth it for the views and the ambiance.
With the famous Bean as your backdrop, there’s nothing quite as quintessentially “winter in Chicago” as ice skating in Millennium Park. Again, admission is free but rental is not — it’ll be a crowded but fun urban experience.
Can you tell we love to ice skate here? Different from your other icy adventures in that this one is located on a rooftop, this skating scenario is complete with downtown views and cozy cocktails. Whether you want to skate or not, it’s a perfectly festive winter destination.
If you’re staying more on the west side of the city (in the West Loop, Fulton Market District, or in Wicker Park/Bucktown), Kaiser Tiger is a multi-level bar just a hop, skip, and a jump away. Not only do they have a large event space, shelves full of games, and a swoon-worthy bar menu, but in the winter they’re home to three ice curling lanes for public use (call ahead of time to reserve a time slot, as they fill up fast on weekends).
Where to Shop
Michigan Ave (or the Magnificent Mile) is probably the most well-known street in the city — it’s home to a ton of luxury stores, gorgeously decorated department stores, and fun pop-ups. Start at Water Tower Place for some edible cookie dough and a glass elevator ride, then travel south, window-shopping the likes of Burberry, Under Armour, and just about everything else you can imagine. (P.S. The original water tower — now next to the Water Tower shopping center — is one of the few buildings to survive the Great Chicago Fire of 1871. It’s an interesting story worth reading.)
Walking through the streets of Chicago’s Gold Coast neighborhood is both aspirational and attainable — you can grab a Starbucks coffee (this is the location where I once ran into Demi Lovato) or a Sprinkles donut (they have a cupcake ATM machine), then walk down Oak Street for window-shopping and real shopping alike. There are LOTS of high-end options (Jimmy Choo, Harry Winston, and Tom Ford come to mind), but plenty of spots for the rest of us — stop into Madewell, lululemon, and Vineyard Vines too. Bonus: this area has LOTS of beautiful homes to look at too — it’s a fashion lover and architecture enthusiast’s dream come true.
Another fun street but one that’s much more off the beaten path, Armitage is full of boutique-y shops and some more unique favorites. You’ll find Chicago-specific stops like All She Wrote and Foxtrot; and some more popular favorites like Warby Parker, LUSH, Outdoor Voices, and Bonobos. Perfect way to spend an afternoon! P.S. Grab a Jeni’s ice cream while you’re walking around — we’re big Jeni fans!
With a perfectly-located Blue Line L stop, Wicker Park’s Damen Ave. and North Ave. are perfect not-too-crowded shopping spots. Visit Shinola, Aesop, Alexis Bittar, LUSH, and a Nike Running store for some familiar items, or check out more exclusive shops like Oak + Fort (where I got my favorite jumpsuit I’ve ever owned), Asrai Garden, Virtu, and RSVP Gallery.
This intersection (and the surrounding area) is so chock-full of amazing stores, you could accidentally spend your entire trip here. Not only are there fashion favorites like Anthropologie, Athleta, and a Nordstrom Rack, but there’s also just about every home store you could want (like a rare CB2 store) and big necessities like an Apple store. Bonus: The L Red Line will take you directly here from downtown!
Where to Eat
Best Eats Under $10
Sultan’s Market — Middle Eastern
If there’s anything I love more than falafel, it’s inexpensive food. Sultan’s Market gives you both! Their menu is filled with cheap and delicious Mediterranean food. They have multiple locations in big areas of the city, so you can shop your heart out AND still have enough for a meal. It’s kind of set up like a Chipotle-style situation. Bring cash!
Wiener’s Circle — Hot Dogs
This small hot dog shop in Lincoln Park has one of the best hot dogs you’ll ever have — and some of the most irreverent commentary in the city. It’s a perfect place to stop in for a snack while doing some wandering around Lincoln Park (and get some foul-mouthed fun in the process). The sign out front is always changing to feature funny and cheeky phrases and commentary on politics or pop culture, and the employees aren’t afraid to give you a little show. You’ve been warned.
Portillo’s — Italian Beef/Hot Dogs
Portillo’s is famous for a REASON — it’s seriously some of the best Italian beef you’ll ever have. They also have great hot dogs, burgers, and crinkle fries (and even a chopped salad that’ll blow the socks off any salad hater, myself included). Want to order like a local? Ask for an Italian beef dipped with all the peppers, and a chocolate cake shake on the side. Deeeelicious!
Small Cheval — Burgers
So if you know anything about burgers, Chicago, or the Food Network, you might have heard that Food Network stars Geoffrey Zakarian and Sunny Anderson called Au Cheval‘s double cheeseburger the best burger in America. While Au Cheval is great and all, they don’t take reservations and there’s ALWAYS a couple-hour-long wait to sit inside their tiny West Loop space. Skip the wait — head to any of the four “small” versions of the restaurant and order their classic cheeseburger. Hint: a single actually has two patties, and a double has three. Yeah, I don’t know either — and their golden fries with garlic aioli dipping sauce. The menu is simple for a reason: burgers, shakes, shots, and beer are all a good Chicagoan needs.
Chicago Bagel Authority — Breakfast
If it’s good enough for Ariana, it’s good enough for us. While Ariana Grande did visit CBA when she performed here in 2018, that’s not the reason to visit — the bagel sandwiches here are so good, someone once snuck a photo of me eating one on the L (I was being pretty embarrassingly enthusiastic, I will say). It’s crowded at breakfast time, but so worth it — they sandwiches are super filling and it’s a great local experience!
Cheesie’s — Sandwiches
Cheesie’s is an entire fast-food restaurant dedicated to specialty grilled cheeses — need I say more!? No, I don’t, but I will — not only does Cheesie’s have knock-your-socks-off delicious fried food and late-night sandwiches, but they also provide a full bar and a colorful experience. I’ve eaten here for every meal of the day, but it’s best known as a late-night spot — grab a Mac (mac & cheese inside a grilled cheese) and a beer, sit down, and prepare to make a few new friends — we’re all family when there’s cheese involved.
Pequod’s — Pizza
If you’re looking for deep-dish magic, you’ve found nirvana. This pizza is so good it will make you cry into your grease-soaked napkin and yes, I speak from experience. Chicago is a pizza town and Pequod’s is its king, which is really all you need to know, capisce?
Maude’s Liquor Bar — French
I cannot say this enough times — Maude’s is my absolute favorite restaurant in the city (nay, the world). When you step inside, you instantly feel like you’re being transported to another time and place (Paris in the early 20th century, to be exact!). It’s the exact kind of place you can lean in close and spend several hours chatting over wine (something the Everygirl team has done many times, in fact) — and the food’s delicious too. They have delicious French staples, but I’m a sucker for their cheeseburger, french onion fondue (ask for extra bread), and chocolate mousse. Pro tip: their drink menu is extensive, but don’t get intimidated. Start your night with a $3 whiskey shot, then keep the table wine coming — a bottle of their table house or red is only $24 (a major bargain for such a great location). If you only go out for one nice dinner on your trip, this is the place.
Paradise Park — Pizza
Located in the eclectic and fiesty Wicker Park neighborhood, Paradise Park is a pizza place with some major sass. Set up to resemble the chicest trailer park you’ve ever seen, PP is home to delicious specialty pizzas and fun cocktails. Its prime time is in the summer, when you can sit under both the stars AND the lights, but don’t worry if you’re there in the winter — the entire outdoor patio is covered when the weather calls for it. This is a great spot for dinner and drinks with girlfriends — it’s loud, delicious, and a guaranteed good time (not an ounce of pretension in sight).
Big Star Tacos — Mexican
Located just blocks away from Paradise Park is another local hotspot — Big Star Tacos brings Chicagoans delicious tacos, killer margaritas, and one of the best patios in the city. We order Big Star to the office far more than we care to admit — but a trip to one of their two locations (the second is in Wrigleyville, and features brunch!) is worth the trek. Order the guacamole and a pitcher of margs — you’re going to want to stay awhile.
Duck Duck Goat — Chinese
If you’re looking to celebrate a special occasion but are over the whole $100-steak-dinner vibe, this is your place. It’s family-style Chinese, so get ready to share. The chilly chili noodles are to die for, so get two orders. They also offer some pretty inventive cocktails, and they do have a carryout option (if solid Chinese food in your hotel room is more your jam).
Tanoshii — Sushi
You don’t go to Tanoshii for your usual sushi meal. When you sit down, “Sushi Mike” comes out and asks your likes, dislikes, and dietary restrictions. From there, he puts together the perfect menu for your table — so expect to eat the best-tasting sushi ever. And FYI, soy sauce is a no-no here. If that’s not a sign of a good sushi place, I don’t know what is.
Labriola — Pizza
It wouldn’t be a Chicago city guide if I didn’t mention deep dish pizza, right!? While there are about a million places you could go for a tourist-heavy deep dish experience, I prefer to guide you to a less-populated option in the heart of the city. Labriola is a great way to taste Chicago’s most famous staple while still enjoying a classy dining experience. If you’re staying in the Loop (Michigan Avenue area), this is just steps away. Note: If you’re looking for more touristy (but still delicious) deep dish, try Gino’s East (most fun), Lou Malnati’s (best sauce), or Giordano’s (best crust).
Quartino — Italian
This is one of Team Everygirl’s favorite places to take out-of-towners. It’s in a great location downtown, so easily accessible from all your major landmarks, yet it feels cozy and snug and charming. It’s always bustling, but it’s not hard to get a table and the food is INCREDIBLE — and yet, it’s not break-the-bank expensive. Plus, every time I have been there, all the waiters are incredibly hot guys wearing futball jerseys, so that is a real win.
Chicago Diner — Vegan
Vegans and vegetarians rejoice! As a self-proclaimed carnivore, I was skeptical about the first time I went to visit this no-meat spot but WOAH is their food amazing! Their meatless “chicken” wings are to die for, and their dairy-free milkshakes are literally iconic (serious, food bloggers everywhere are obsessed).
Wheat’s End Cafe — Gluten-Free
Wheat’s End has the vibe of your typical airy, beautiful, and cozy cafe, but everything on the menu is gluten-free. However, even the biggest of carb lovers can enjoy their menu. Their delicious bagels might change your opinion on GF options!
Parachute — Korean Fusion
I’ve never actually been to this Korean fusion restaurant nestled up in Avondale, but Kelly’s brother raves about it (she swears he only visits her to have an excuse to go). Started by a husband and wife team, the menu boasts plump East Coast oysters (heaven), spicy pig’s ears, and hot pots that will basically punch you in the face with flavor.
Avec — Mediterranean
Avec is home to some of the most delicious shared plates in the city. Featuring Mediterranean-inspired dishes in a rustic-chic setting, you can’t go wrong visiting for any meal, brunch, or dinner. At certain times of the year, they host a Friends of Avec brunch series — where other restaurants take over the kitchen and bar to allow visitors to try a variety of tastes. They’re also known for their wine selection, with a wide range of bottles available at price points as low as $20!
The Allis — American
Located in the ground floor of Soho House (but open to the public, even if you’re not staying there), The Allis offers a perfectly chic brunch spot with an easily approachable brunch menu. Dine on classic breakfast favorites or take part in the famous Allis cheeseburger, then walk it off while exploring the always-hopping West Loop neighborhood. Those who love an Instagrammable meal will LOVE The Allis.
Summer House Santa Monica — American
If you’re looking for a classy spot for a pretty well-mannered brunch, this is the move. While you could come here for lunch, dinner, or drinks too, brunch is when Summer House truly shines. With a retractable glass ceiling, it’ll feel like summer no matter what the weather’s like — and a seasonal rosé cart doesn’t hurt either! Their wide selection of brunch sandwiches and entrees is perfectly complemented by the tropical decor and the festive cocktails.
Fremont — American
Bottomless brunch is a Chicago staple — and nowhere does it better than Fremont. While Fremont is a club at night, the daytime vibe here is pretty similar — a brunch deal gets you unlimited access to mimosas, a buffet, a doughnut wall, a carving station, and boozy dessert ($40 plus add-ons for drinks). Complete with a DJ and dance floor, a weekend day spent at Fremont is literally just a big night out in the daytime. If you’re in town for a bachelorette party, this is a great option.
Barcocina — Mexican
Barcocina is another bottomless brunch option – but it’s definitely more of a sit-and-talk vibe than Fremont is. A more budget-friendly way to experience unlimited mimosas, Barcocina also offers a Mexican food buffet that will do your taste buds well. This a great spot for large groups, and it’s nice to note that their mimosa options range past the typical orange juice — they have other juice options to pair with your champs as well!
The VIG — Gastropub
You have to go to The Vig for brunch so you can experience the gorgeous building in daylight. It looks almost out of a movie aka it’s what Instagrams are made of for the locals. Wear your most stylish outfit here! The chicken biscuit sliders are heavenly. If you want to go crazy (maybe a 21st bday or bachelorette celebration!), get a mimosa tower. You (except maybe your liver) won’t be disappointed.
3 Arts Club Cafe — American
Located inside Restoration Hardware in Chicago’s Gold Coast neighborhood, 3 Arts is basically an indoor botanical garden/cafe. Not only is it easily the most Instagrammable spot in town, but they also have delicious food and an extensive wine list. I love the truffled grilled cheese and a glass of prosecco!!
Doughnut Vault — Doughnuts
Not only is a trip to Doughnut Vault a super ‘grammable moment, but it’s a tasty one to boot. They feature a variety of your all-time favorite doughnuts (like old fashioned and sprinkles), but they also have a rotating selection of specialties as well. Be sure to check out their online menu to see what the specials will be when you stop by — and don’t forget to snap a pic!
Mindy’s Hot Chocolate — Dessert
Owned by one of the most badass women on the planet, Mindy’s could have a place in any category on this list. It’s a restaurant, bar, brunch spot, AND dessert heaven — but its unique range of sweets reigns supreme. Order a decadent pastry or artisan ice cream, but be sure to pair it with one of Mindy’s signature hot chocolate creations for a true treat.
Bang Bang Pie & Biscuits — Bakery
IMO, there aren’t enough places serving up homemade pie by the slice, so thank God for Bang Bang. They’ve got your classics like Key Lime and experimental flavors like Spumoni (pistachio and cherry). If you don’t want your dessert first, try one of their amazing biscuit creations or a southern comfort like grits. I’m #blessed to live across the street from one – my personal order is a bacon biscuit and a slice of cranberry apple to go.
Maison Marcel — French
If you’re looking for a quick place to rest your feet, grab a swig of tea, and munch on a macaroon, then girl I gotchu. This coffee shop is eminently ‘grammable and as a bonus, it’s actually delicious. Win, win. Plus, it’s in a great location for shopping, way more food, and meanderings by the lake.
Drinks with the Girls
This hidden hotspot truly makes you feel like you’re in France — with delicious French cuisine, a large wine selection, and a classy patio, RM Champagne is an easy way to lose a few hours and down a few bottles of wine. The lighting is dim and the decor is stunning, so this spot could double as a perfect place for a romantic evening.
This little hidden bar is downtown (convenient location for visitors), underneath the (also truly wonderful) Pops For Champagne. Telling the bouncer you’re headed to Watershed also feels ~ very cool ~ and like you’re in some kind of secret club situation. Once you get downstairs, the bar is dim, the drinks are excellent, and the music is fun and upbeat but not “what? what?! wait, what?” loud. Win.
In the heart of River North (a great spot for people who want to experience some of Chicago’s best nightlife), Joy District offers dancing, great drinks, and tons of fun. It’s somewhat of a club/bar hybrid — you can book tables and get that typical club feel, all without the high price of a fancy nightclub. In the summer, they open up the roof, and it’s a blast. Out-of-towners will love the scenery!
Not only is the pizza here omgsogood, but it’s the vibe here that really sets it apart from every other pizza place in the city. All three locations of this bar/restaurant have amazing outdoor spaces — and both are great places to lose yourself for an afternoon and make some new friends (and meet some boys — who said that!?).
Casual, quirky, and always buzzing, Green Street is Team Everygirl’s go-to happy hour spot (which almost always turns from happy hour into dinner into late-night drinks…). You can go for the food (slabbed meat, sandwiches, and comfort food sides), but you’ll want to stay for the vibe. The only tables are long and cafeteria-style, lending to the feel that you’re amongst lots of friends. The drinks are pretty cheap, the music’s not too loud, and they play ’80s movies on TVs in the background. The outdoor section feels like something out of 1920s NYC, but the indoor section is great too (meaning you can go in any season and have a good time). Quick anecdote: I almost ALWAYS forget something, drop something, or leave something when I’m there. The bartenders are so friendly and always help me find my stuff with a smile. I seriously LOVE it here.
Intimate and electric, The Green Mill was Al Capone’s prohibition hot-spot (ask your bartender for his special booth) and stills stands as the city’s home for some of the best jazz you’ll ever hear. Head to Uptown late on a weekday night for live swing-dancing, Sunday afternoon for the country’s OG slam poetry reading, or Saturday evening for some smooth jazz and cocktails. If you’re feeling brave, order a shot of Malort, a Chicago classic you won’t soon forget.
If you’re looking for dancing, this is your jam. Each night is themed — ’80s, ’90s, early aughts, etc. — and music videos are played on a giant screen in the middle of the dance floor. You’re basically dancing WITH Lionel all nightttttttt lonnnnnnnnng. There’s also a great front room that is a more chill bar with pool and foosball and the like in case you’re with some people who are ~not about~ going for it on the dance floor. I recommend ordering a long island ice tea (lean into it, baby) and grooving the night away
When you walk into Three Dots and a Dash you literally feel like you are entering another world. You go through an alley into the back of a restaurant that magically transforms into the most magical Tiki bar you could ever imagine. Their drinks are AMAZING and all of them are super fun — hello smoking treasure chest full of rum.
Lottie’s would be super cool no matter what (it’s a laid-back neighborhood bar with cheap drinks and a crowd that’s ALWAYS down for dancing), but it’s made even cooler by the fact that it’s the former set of the bar frequented by characters on Chicago Fire. The show has since built a set to resemble the bar, but all season one bar episodes were filmed right at Lottie’s. It’s a cool piece of trivia, a great spot for friends, and a must-visit for Chicago Fire fans!!
Any list of Chicago bars would be incomplete without mentioning Wrigleyville’s most famous (infamous?) spot. Complete with a massive dance floor, a dueling piano bar, and BATTING CAGES (yes, really!!), this is the perfect spot to cut loose before or after a Cubs game (or anytime, really). The crowd here is really young, loud, and rowdy — I highly recommend it for a crazy night with the girls.
You didn’t think I’d forget about karaoke, did you? You come for Bub City’s barbecue, but you stay for the karaoke. Here for a week, not a weekend? You can sing karaoke with a live band on Tuesday nights. Bonus: they also have a brunch menu perfect for those who had just a little too much fun the night before.
As one of few 4am bars in the city, The Hangge-Uppe is famous for being your squad’s perfect place to end the night. Two floors of late-night dancing will make you sad to head back to your hotel, but don’t worry — this fun spot is open til 4am Wednesday through Sunday.
Rooftops and Patios
Not only is this chic spot a coffee shop, event space, and bar/restaurant, but it also has one of the most stylish outdoor spaces on the west side of the city. Conveniently located right near the L Blue Line, the cozy patio will make you forget you’re in the middle of a bustling city. Plus, a menu that includes “Mac and cheesefries” is a winner in our book.
If you’re in town with a group, Royal Palms is the perrrrfect place to visit. There are delicious drinks and a rotating selection of food trucks to satisfy your needs — and tons of oversized games and shuffleboard down on the main floor. If you want to get in on the rooftop action though, head upstairs to their seasonal Lido Deck, which features a tropical experience right in the middle of Wicker Park.
Beach lovers, rejoice! No day at the beach is complete without a tropical cocktail (or mocktail) in a totally breezy location. Brand new to North Avenue beach is the Shore Club, a part-indoor, part-outdoor beach club featuring fun music, beachy decor, and a big selection of food and drink. Lounge on outdoor couches or belly up to the indoor bar — it’s the perfect complement to your Lake Michigan beach day.
When the weather is warm and the sun is out, I always crave a glass of rosé on the J.Parker rooftop. This gorgeous bar/restaurant is at the top of the iconic and historic Lincoln hotel, conveniently located in Lincoln Park, so you can cool off after a day at the zoo or enjoy the perfect summer night out. With inventive cocktails, delicious food, and views of Lake Michigan and the entire city skyline (get there before sundown for prime Instagram pics), you won’t want to spend your summer night in Chicago anywhere else.
There’s no doubt in my mind — Cindy’s offers the absolute best views in the city. Located on the top floor of the Athletic Association Hotel, Cindy’s overlooks Millennium Park and a stunning view of the lake. Get there early, order yourself a French 75, then snag a spot by the outdoor railing — the colors during sunset lend themselves to an unforgettable vista.
For a luxurious cocktail experience you won’t soon forget, head to the rooftop lounge of the LondonHouse Hotel. Housed on two floors, the large-but-cozy bar offers exceptional food and drink options, as well as breathtaking views of the city around you. Located right in the center of all the downtown action, the LH Rooftop is a piece of your trip you won’t soon forget.
As much as we love the lake (and really, we do), dining along the river can be just as fun of an experience. The downtown City Winery location is located directly on the river — so you can wait for your table and sip your from-the-tap wine on steps or benches with perfect views of passing boats and the surrounding architecture. Once seated, you’ll be treated to a comfortable menu of delicious favorites. This is easily the kind of place where you accidentally spend hours and hours — just don’t forget your sunglasses!
For an authentic summertime-in-Chicago vibe, no trip would be complete without a stop (or a stay) at one of the two Parson’s locations. The food is unpretentious, the drinks are unique and cheap, and the patio features large picnic tables and ping pong. If you want to hang out where Chicago 20-somethings do, you’ve found the spot. (I’ve only been to the Logan Square location, but the brand new Lincoln Park location is a bit more centrally located — and is just as fun.)