There’s a saying we Chicagoans love to overuse: “You live through Chicago in the winter so you can enjoy Chicago in the summer.” It may sound crazy to anyone who reads our January/February headlines (“Chicago Colder Than Antarctica, Alaska, North Pole,” January 2019), but it’s true — the second the thermometer reads 50 (okay, 45) and Cheryl Scott predicts sunshine and clear skies, we run outside faster than Kris Bryant runs the bases.
What’s so great about Chicago when it’s warm out? you may ask. Oh ye of little faith — what sets Chicago apart from other cities in warm climates is its ownership of a few key gifts from Mother Nature: freshwater beaches, 18.5 miles of lakefront beauty, and a lazy river that runs directly through the heart of downtown. So while you can sip a mojito beachside in California or en rooftop in NYC, Chicago’s the hotspot that allows you to do both all at once (take that, other cities!).
Have I done it? Have I convinced you? If you’re now set on making a trip to the Windy City (or you already live here and are ready to embrace all the summer has to offer), have I got the thing for you. Here, I’m sharing alllll the best things to do, places to see, and drinks to drink in the city that never sleeps (and by that I mean, the city that sleeps around 2am because that’s when the bars close because we gotta get up early for brunch) — cheers!
Summer House — American (Lincoln Park)
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.
Barcocina — Mexican (Lincoln Park)
Barcocina is a bottomless brunch option – but it has a nice sit-down-and-talk vibe as opposed to being too wild and crazy. As 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! ($49.95/person gives you an entree, two hours of unlimited drinks from a select menu, and gourmet chef stations)
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. Thursday through Sunday through Labor Day, they launched Summer Club At Fremont, a pop-up with new drinks, happy hour specials from 5 to 9 pm, and lots of summer-y decor! If you’re in town for a bachelorette party, this is a great option. ($40 for food stations, plus add-ons for drinks)
Troquet — French (River North)
Whenever anyone asks me for a brunch recommendation in the city (no matter the season), I always come back to Troquet. The French-inspired menu is full of delicious favorites (I love the Croque Madame, but the burger with fried egg is good too!), and the bottomless mimosa deal is relatively non-pricy (For $29 you get a brunch entree and 1.5 hours of unlimited bubbles). You can sit inside or out, but even if you elect to sit inside, the huge front windows allow you to enjoy the weather without getting bugs in your drink. If you’re deciding between a few places, I can almost guarantee this will be a hit. ($29 for a brunch entree and 1.5 hours of mimosas)
Beatrix — American (several locations)
Real talk — the Everygirl team goes to Beatrix so often they should almost pay US to eat there. Not only is it the most delicious grab-and-go place to stop for lunch and the birthplace of the gluten-free cheese popovers that Josie and I split every single workday for lunch, but each of its several locations also features a delightful patio and a large, healthy menu. The brunch entrees are delicious, and it’s not hard to stick to your goals here — they have great salads, protein-rich sides, and hearty sandwiches and bowls. So good, won’t break the bank, and a fun patio? Perfect.
The Allis — American (West Loop)
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.
Brickhouse — American (Wrigleyville)
Whether you’re hitting up a Cubs game or not, Brickhouse is a really fun place to feel the camaraderie and sportsmanship of Wrigley Field. Located literally right outside the stadium, Brickhouse offers an unlimited drink deal and the brunch buffet of your dreams. The outdoor lounge chairs and tables are the perfect place to soak up some sun for an afternoon, and it’s also great for a group. I accidentally stumbled upon an engagement party there once! ($30 all-you-can-eat buffet and $20 mimosa package)
The Dawson (West Loop)
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 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.
Paradise Park (Wicker Park)
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. You can sit under both the stars AND the lights — the entire restaurant is outside. 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).
Green Street Smoked Meats (West Loop)
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 outdoor section feels like something out of 1920s NYC — exposed brick, long cafeteria tables, cobblestone walkways, and lots of string lights. 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.
Joy District (River North)
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!
Parlor Pizza (several locations)
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!?). Order the prickly pear margarita — SO GOOD.
Royal Palms Shuffleboard (Wicker Park)
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.
Shore Club (Lincoln Park lakeshore)
Beach lovers, rejoice! No day at the beach is complete without a tropical cocktail (or mocktail) in a totally breezy location. Shore Club, a part-indoor, part-outdoor (renovated!) beach club featuring fun music, beachy decor, and a big selection of food and drink, has been a North Avenue Beach staple for the last three years. Lounge on outdoor couches or belly up to the indoor bar — it’s the perfect complement to your Lake Michigan beach day.
Parson’s Chicken & Fish (Logan Square or Lincoln Park)
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.)
Happy Hour Deal: 3-6pm weekdays — $2 shots, $6 drumsticks, and more (call for exact details based on the day)
Waydown (West Loop)
The Waydown rooftop is located inside the Ace Hotel, and it’s one of the most underrated views of the city. Viewing from the far-ish West Side offers a stunning view of the skyline, and the covered rooftop offers some nice protection from the elements. It’s a unique vibe in a creative/hopping part of town — definitely one to check off your list (and take some pics for the ‘gram).
Happy Hour Deal: 4-6pm Tuesday-Friday — $6 rosé and rosé cider, $3 Old Style cans, various snacks
Sepia (West Loop)
While it’s not the most picturesque patio in town, Sepia just may be one of the most convenient. Located just a hop, skip, and a jump away from the Metra stations and just about every train line, Sepia is the perfect spot for a post-work cocktail. The happy hour menu consists of cocktails, wine, beer, and snacks — and it’s the best under-$10 French 75 I’ve ever had.
Happy Hour Deal: $7 cocktails, wine, beer, snacks; $10 wine flights
Somerset — American (Gold Coast)
I couldn’t decide if this should go on the “brunch” list or the “dinner” list, because the truth is that it’s amaaazing for both. This highly Instagrammable spot is so chic inside and out, but the patio in the heart of Gold Coast truly shines. Bonus: they have a cool “progressive happy hour” with the rooftop bar in the same building — you start at Somerset, then go upstairs to Devereaux’s swanky rooftop. Perfect evening out!
Le Colonial — Vietnamese (Gold Coast)
Le Colonial is arguably the best place to go in Chicago for both authentic Vietnamese food and an upscale atmosphere. The Chicago institution was created in celebration of 1920s French Colonial Southeast Asia, and it’s everything you would expect it to be and more. The fresh, exotic flavors mixed with stunning decor (both inside and outside) and high-end service make it the perfect date night spot or GNO destination. Whether you go for the romantic, elegant atmosphere or the refreshing cocktails, you’ll stay for the food that is not only delicious, but will make you feel transported.
Beatnik on the River — Global (The Loop)
It doesn’t get more picture-perfect than an evening at Beatnik. Whether you’re coming in for a drink and a few snacks or you’re looking to make a real night of it, Beatnik is definitely the place to go. While away the long summer nights in Beatnik’s outdoor space and pretend you’ve transported yourself far away from the hustle and bustle of the city.
LUXBAR – American (Gold Coast)
LUXBAR is a Chicago staple and for good reason. The food is consistently delicious and the martinis are to die for. But the real icing on the cake is people watching on the patio on a Friday or Saturday night. LUXBAR sits in the middle of downtown’s Ritzy Gold Coast neighborhood, and the characters walking up and down the Rush Street corridor will not disappoint.
Etta — Italian (Bucktown)
Etta is a newcomer — the restaurant is barely a year old, but they’ve solidified their place in Chicago’s food scene pretty quickly. Sitting on North Avenue in Wicker Park, you can smell the wood-fired oven from blocks away. The space feels very warm and comfortable in an incredibly modern way, and the food all tastes like it has been made with the freshest ingredients and a ton of love. I can’t imagine a better place to dine alfresco and finish off a bottle of wine under the stars (jk, it’s Chicago, you can’t see stars!)
Big Star — Mexican (Wicker Park or Wrigleyville)
Located just blocks away from Paradise Park is another local hotspot: Big Star Tacos, which 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.
Maude’s — French (West Loop)
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.
City Winery Riverwalk — American (The Loop)
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!
The Robey (Wicker Park)
As the tallest building in Wicker Park/Bucktown, The Robey Hotel offers one of the absolute best views of the skyline and surrounding neighborhoods — AND its rooftop has a pool (what more could you want!?). The rooftop pool/lounge/bar opens to the public at 11am (and 9am for hotel guests), so you can spend an entire day (or just an afternoon or evening) relaxing by the pool and enjoying libations from the Cabana Club.
Cindy’s (Michigan Avenue)
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.
The J. Parker (Lincoln Park)
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.
LondonHouse Rooftop (The Loop)
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.
Cabra (West Loop)
Cabra is the brand-new rooftop destination from the brilliant culinary mind of Stephanie Izard (first female chef to win Top Chef, as well as the woman behind several of our other favorite Chicago restaurants). It’s located on top of the new Hoxton Chicago hotel, and its Peruvian-inspired menu perfectly compliments the STUNNING decor and idyllic rooftop vibes. It’s pretty large and therefore perfect for either an intimate get-together OR a fun group hang.
Aba (West Loop)
An absolute urban oasis, Aba is located on one of our favorite streets in the West Loop — right in the heart of the Fulton Market District. Whether you’re going for a protein-rich meal or just a drink, the ample greenery will make you almost forget you’re in the middle of a bustling city — but the skyline views won’t let you leave town for too long.
Take in a baseball game.
Chicago is home to so many amazing sports teams — but it really shines under the lights of Wrigley Field (the Cubs) and Guaranteed Rate Field (the White Sox). You can find pretty cheap bleacher tickets (if you’re over 21), which is a really fun way to meet new people and experience the game in close quarters. Bonus: some bars host pregames with free shuttles to the games, so you can eat and drink all you want before you go, and save money at the actual game (my friends have done Reggie’s before).
Take a brewery tour.
There are SO many breweries in Chicago — and all the best ones offer tours of their unique facilities. I’d say the ones you’d hear about the most are Lagunitas and Goose Island, but there are certainly options for any taste. Check out 5 Rabbit Cerveceria & Taproom for Latin-inspired beer or Lake Effect for a small-yet-inspiring taproom. I love this list of 16 of the best options!
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. BONUS: There are SO many beaches along the lakeshore — Oak Street’s is a bit more relaxed, while Montrose Beach is less busy than its downtown counterparts.
Architecture Boat Tour
While it honestly may sound boring, the architecture boat tour is truly anything but. Hop on board 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 do with a date or with a group. (Note: a lot of different tour companies do these tours — I’ve used Wendella!)
Kayak along the Chicago river
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!
Movies in the park
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.