The Everygirl’s Weekend City Guide to Chicago, IL

It is with enormous excitement that we finally present to you our weekend city guide to Chicago! What can we say about this glorious city? Not enough! Home to The Everygirl headquarters, one of the best food and cultural destinations in the U.S., and a place that has something for everyone, this city has truly captured our hearts. If you’re lucky enough to be traveling here this summer (because let’s face it, that is truly when this city shines), we hope our tips will help you have the best girls’ weekend possible!

Here’s how we’ve broken it down for you…

Budget Hotels (less than $150/night)
Mid-range Hotels ($150-300 night)
Treat Yo’self Hotels ($300-500 night)

Relax and Indulge
Outdoor Fun

Best Eats Under $10
Best Dinner and Brunch Spots
Drinks with the Girls


Where to Stay

Budget Hotels (under $150/night)

Hotel Allegro

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The newly redesigned Hotel Allegro feels leaps away from budget accommodations—the chic hotel is both affordable and luxurious all at once. Close to a subway station and just steps away from Millennium Park, Hotel Allegro makes for a convenient place to stay while in Chicago. There are iHome docking stations in each room, in-room spa services, and best of all, the entire hotel (like all Kimpton properties) is pet friendly.

Inn of Chicago – Magnificent Mile
If you’re lucky enough to spend the weekend (or longer!) in Chicago, you’re also fortunate enough to experience the city’s amazing array of hotels that feel luxurious at budget prices. The Inn of Chicago is one of those places—the good specials and reasonable prices mean you can spend a stylish and seemingly high-end weekend at this hotel at a budget price. As the name suggests, you’ll be just steps away from the famed Magnificent Mile (and all the shopping!).

The Freehand

photo by Adrian Gaut via

The new Freehand property sounds too good to be true—you’ll never believe this beautifully appointed property is actually a hostel. Everything from the sheets to the art has a pristine, fresh feeling to it and if you don’t mind sharing a room you can save even more money. For a more secluded yet still affordable choice, opt for one of the private rooms. Cocktails, coffee, and eats are available on-site, giving this hostel the look and feel of a well-designed hotel. Located in River North, the centralized location makes it easy to get around. Those on a budget will be glad to know that there is a daily complimentary breakfast included in the price of your room.

Mid-range Hotels ($150-300/night)

The Wit Hotel

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Those looking for a comfortable hotel with high-end touches and a sense of humor will feel right at home at the aptly named Wit. Though many hotels in Chicago excel at one service or offering, The Wit Hotel has a little bit of it all. The design is creative and unexpected, the beds are comfy, and many of the rooms feature amazing views of some of Chicago’s most visited sights. Don’t worry if you end up with a room without a view though—spend your evenings sipping wine at The Wit’s rooftop lounge to enjoy beautiful views of the city.

Acme Hotel
Located just a stone’s throw from the Magnificent Mile, the Acme Hotel is perfectly situated in downtown Chicago. Close to shopping and many of the city’s attractions, the hotel is a great option for any traveler. The Acme Hotel houses hip, beautiful decor, and furnishings that we love but the hotel really shines when it comes to the perks and extras they offer to guests at no charge. Free coffee delivered to your room any time you’d like, free access to Google Glass, and free hotspots to go (meaning you can travel all around the city while staying connected to high-speed wifi and avoid roaming fees) are just some of the stand-outs. Acme is committed to providing an innovative experience to their guests and their effort really shows.


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Aloft Hotels are almost always a great option for travelers looking for a stylish yet affordable place to rest their heads; the Aloft Chicago City Center is no different. Close to all the sights, home to a fun bar and lounge, and highly rated, the Aloft will be loved even by the pickiest travelers. Located in the River North neighborhood, the hotel is close to some truly amazing Chicago restaurants. We recommend checking in, getting settled, and spending an evening exploring the neighborhood.


Splurge Hotels ($300-$500/night)


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Those wanting to pamper themselves in style should look no further than the Thompson. From the moment you step foot onto the property, you’ll feel the luxurious yet comfortable vibe the hotel gives off. Located among the mansions of Chicago’s Gold Coast, the hotel will have you feeling like a local in no time. Stunning city views top off an already incredible property.


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The details that went into the design of the Public are what make the property truly worth a visit. Part boutique hotel and part luxury property, Public creates a personalized and comfortable experience for all guests. A visit to the Public’s library coffee bar (serving up fresh La Colombe coffee!) is an absolute must. In the evening, the coffee bar transforms into a wine bar offering the best of both worlds. The guest services team at the hotel prides themselves on providing a truly personal, customized experience to guests—your time there will be truly be a standout.

Hotel Lincoln

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Vintage charm in the heart of Chicago makes Hotel Lincoln a solid choice for any traveler looking for a luxury stay that is both unpretentious and comfortable. Hotel Lincoln’s location in (you guessed it) Lincoln Park means that you’ll enjoy a more peaceful stay while still being close to the action in downtown Chicago. Each room is decorated with a preppy, vintage inspired design. The real standout, however, is the property’s famed rooftop bar, J Parker (scroll down to our “Best Spots for Drinks with the Girls” section for more details), a key highlight of the property.

What to Do


Green City Market

photo by Jennifer Kathryn 

Who doesn’t love a good farmers market? The mission of Green City Market is to provide more diverse, high-quality foods to the residents of Chicago. Even if you’re just visiting, the market is a great place to stroll around for an hour or two picking up market snacks along the way. The market sometimes holds chef demonstrations as well if you’re in the mood to watch the pros at work. Just note that the market isn’t open during the coldest months, and that hours do vary depending on the time of year. Check their website before heading over.

Free Concerts in Millennium Park

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Headed to Chicago in the summer? Stop by Millennium Park at some point to catch one of the free concerts that the city hosts. Whether you’re a jazz lover or just someone who wants to soak up some local music, the concert series will have you covered. If you can’t make it for one of the musical performances, check the site for other options. Throughout the summer, the park also hosts workout classes, movies, festivals, and more.

The Comedy Bar
Frequently lauded as one of the best places in the city to catch a comedy show, The Comedy Bar is a nice option for those looking for a laid back, laughter filled evening. Located in River North, the club is easily accessible and boasts affordable ticket prices—a good option for any budget. Didn’t get the chance to grab dinner before your show? Not a problem! You can order food and drinks there as well.

Chicago Music Venues and Festivals

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As a city that has put out some truly iconic artists, Chicago will please just about any music fan. With amazing venues throughout the city and some of the most anticipated festivals in the country, heading to a live show while in the city is highly recommended. Check here to find a venue that matches your taste, or plan your trip around one of the famed music festivals (like Lollapalooza) that the city hosts each year.


Art Institute of Chicago

photo by Jennifer Kathryn 

Creative types and art lovers will want to spend days (if not more!) at the Art Institute of Chicago; the institute is world renowned for it’s collection. Though the museum is best known for its impressionist art, there are a variety of other art styles showcased as well. Don’t let the vastness of the museum overwhelm you—guided and self-guided tours are available every day and are a great way to see some of the museum’s best offerings.

Lincoln Park Conservatory
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The Lincoln Park Conservatory provides a welcomed respite from the fast pace of the city. Traveling to Chicago in the winter? Stop in to see palms and greenery even in the harshest of weather conditions. The conservatory has a variety of tropical plants, koi fish, and orchids to name a few. You don’t have to be a gardener or plant lover to enjoy the grounds. There is beauty at just about every turn at the conservatory making it a fun (and free!) stop on your tour of Chicago.

Shakespeare Theater
The theater scene in Chicago has a wide span, but the Shakespeare Theater is one of our favorite ways to take in this thriving part of Chicago culture. Located on the Navy Pier, you’ll enjoy a stunning setting along the lake in addition to a beautiful, well appointed theater. Though one might assume that seeing a Shakespeare play will cost you, a special program allows patrons under 35 years of age to purchase tickets for just $20!


Outdoor Adventure

The Beachphoto via

If you are traveling to Chicago in the winter this option probably isn’t the best for you! Lucky enough to be traveling to Chicago in the summer? A beach visit is a must! There are actually a few different beach options in the city: Montrose beach is the place to be for for dog lovers; Oak Street beach is another great option that is close to everything and easy to access; North Avenue beach is for the fun crowd.

Divvy Bikes

photo by Jennifer Kathryn 

Not keen on riding the L (public train) or ordering an Uber while in Chicago? Lucky for you, Chicago has a wonderful bike sharing system called Divvy Bikes. For $7, you have an unlimited number of bike trips lasting 30 minutes or less within a 24-hour period. Biking in a major city may give you a pause, but Chicago has hundreds of miles of bike lanes making this a safe, fun, and affordable way to enjoy the city. For a list of stations, visit the website here for a detailed station map. If you’re planning on renting a Divvy Bike during your stay, make sure to review these riding tips so you are aware of biking laws and rules.

Lakefront Trail

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The lakefront trail is a nearly 20 mile long recreational area that runs along Lake Michigan. A great place for a run or bike ride, the trail boasts beautiful views of the city and is a good option if you want to sightsee while getting in a workout at the same time. The trail runs near many of the most famed Chicago attractions so we recommend maximizing your visit by reviewing a trail map before setting out.


Relax and Indulge 

The Cowshed

photo by Jennifer Kathryn 

Located in the chic, sophisticated Soho House is the Cowshed Spa. Head there for a simple manicure, a full-body massage, or just about anything in between. There are several different treatment rooms, each one more relaxing than the last. Though this certainly isn’t a budget spa option, it’s a great place to head to for a special occasion or just to treat yourself.

Those looking for the ultimate relaxation experience will feel complete at peace in Allyu. A strong attention to detail when it comes to spa treatments makes this place a stand out. With full day options, don’t be surprised if you spend more time here than expected!

Blueberry Moon
An affordable spot where you can get nail treatments, massages, or your hair done, there are many options at Blueberry Moon; it’s a great spot to head to with a group who are all looking for something a little different.

Johnathan Breitung Salon and Spa

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This spa is all about a luxury feel allowing patrons to rejuvenate themselves from the inside out. The upstairs area of the property is a salon, while the downstairs area is an inviting spa. Offering a variety of pampering treatments, it’s a great spot to head to before a night out on the town.



Randolph Street Market

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To experience Randolph Street Market, you’ll have to plan your trip strategically since it’s only open during select times/dates—but trust us, it will be worth it. Vintage and antique lovers will fall in love with the seemingly endless rows of vendors the market boasts. The many food and drink vendors are the perfect spot to turn to after a long day of shopping.


Armitage Avenue Shopping

photo by Jennifer Kathryn 

In the mood to stroll and shop? Head to Armitage Avenue to visit some of our favorite shopping destinations in all of Chicago. Fun boutiques, trendy shops, and unique home decor stores are just some of what you’ll find.

The Magnificent Mile
Could we really leave this off the list? No! The quintessential Chicago shopping experience exists at the Magnificent Mile. Though you may be doing a whole lot of window shopping as many of the shops are highend, it’s a fun afternoon trip to experience with a few of your best girlfriends.


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A cute boutique with a good dose of charm, there’s a lot to love about Penelope’s. The owners have a keen eye for what looks good and the result is a store bursting with inventory you’ll want to take home. Their emphasis is on value and long-lasting, high quality items—so you’ll take home something that you not only love, but that will last forever. They sell women and men’s clothing and a handful of home items.

A place that seems too good to be true, P.O.S.H. is the place to go for a truly unique, authentic souvenir. The owners of the story scour the city and beyond for vintage and flea market pieces and their style is spot on. Home decor fiends will love searching for unique treasures here.

Art Effect

photo by Jennifer Kathryn 

We know we technically we already told you about Armitage (the home of Art Effect) but this little shop it too good for a just a quick mention. Home to some of the most unique and artistic finds in Chicago, it’s more than worth a visit. From cookbooks to dresses, they have a stylish version of just about everything. It’s a great spot for a one-of-a-kind gift to take back home.

Where to Eat


Best Eats Under $10


photo by Jennifer Kathryn

What used to be a stand at a farmer’s market in Chicago is now a full blown cafe for you to enjoy in Lincoln Park. Floriole specializes in pastries, but also has a wide offering of sandwiches and salads made with fresh ingredients, most of which are sourced from local sustainable farms. For under $10, you can snag a morning pastry and a coffee before heading out to explore. It’s an easy, casual lunch spot as well with most sandwiches and salads coming in at less than $10. It won’t break the bank, and it’s fresh ingredients and cute design will leave Floriole at the top of your list!

Mario’s Italian Lemonade
A summertime staple in Chicago, Mario’s Italian Lemonade is a small frozen lemonade stand that has been around since the 1950s. On hot days, there will most definitely be a line, but soldier through! Known for their flavorful shaved ice, the stand uses real fruit in their treats, and is unparalleled in the city. Just remember, the stand is only open during the summer months so plan your visit accordingly!


photo by Jennifer Kathryn 

Though you may have had Intelligentsia in New York or Los Angeles, the coffee powerhouse calls Chicago it’s home and birthplace. With a few different locations in Chicago, Intelligentsia is one of the best places for a cup of coffee in the city. Cozy up with a latte and a pastry before starting your day or stop in for a midday pick me up. Take a look at their list of Chicago locations to find one near your hotel.

Doughnut Vault

photo by Jennifer Kathryn 

Can anyone really say no to doughnuts? As the line out the door may suggest, Doughnut Vault is a great option in the city for a quality doughnut. Creative flavors and a hand-crafted, personal touch is what really makes this place stand out. Because the doughnuts are created by hand and in small batches, we recommend getting there early so that you can have your pick of the crop before flavors begin running out (and they will!).

Blue Door Farm Stand

photo by Jennifer Kathryn 

Blue Door Farm Stand offers farm-to-table eats in the Lincoln Park neighborhood. An expansive list of grilled cheeses (which is what we recommend trying first!), cold-pressed juices, and a variety of small bites and salads means the cafe will please just about any palette. This is perfect if you’re traveling with your ultra-healthy friend who has a juice every morning while you’re more of a breakfast sandwich and coffee kind of lady. Their menu changes often to highlight seasonal ingredients so you’ll get the best of the best regardless of what you order.


Best Dinners and Brunches

Big Star

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Located in Wicker Park and practically an institution itself, you simply must carve out some time for a dinner at Big Star. A menu filled with tacos, Mexican street food, and a number of great cocktail options, it’s easy to see why tourists and locals alike flock here. Though the drink menu is beer and bourbon focused, no one will look twice if you order a margarita! Just plan ahead as the restaurant is cash only, and can get very busy on weekends.

photo by Jennifer Kathryn 

Girl and the Goat or Little Goat
If you’re anything like us, you’ll probably fall in love with this place as soon as you see the cozy interior. Serving up modern American cuisine, Girl and the Goat strives itself on providing their diners with new, innovative dishes. With a great selection of wines, and a menu that will please just about any foodie, Girl and the Goat is one of our favorite picks for dinner with the girls. Be sure to book reservations well in advance (several weeks, if you can), or plan to go during an off-time to avoid long waits.

Avec is the place to go for sharing small plates, a good bottle of wine, and great conversation. Affordable prices, and an array of Mediterranean inspired dishes make Avec one of our favorite places to spend an evening in Chicago. Though we love dinner service at Avec, the restaurant is also open for lunch or brunch making it easy to work into any traveler’s schedule. As if the food wasn’t enough, an award-winning interior means you’ll truly never want to leave.

If you’re looking for a bit of a splurge, look no further than Bavette’s. Perfectly cooked steaks, oysters, and a great cocktail menu should be enough to convince you that the higher prices are worth it. The ambience is beautiful, setting the tone for a perfect girl’s night. Highlights include their bacon, bone marrow, and of course, the steak.

The Bongo Room
A brunch time favorite among locals, The Bongo Room is a great spot to catch a lazy brunch with your girlfriends. With a few different locations around the city, you’ll want to review their site to determine which one is closest to where you’ll be. Serving up fresh and seasonal dishes in a creative way, it’s a solid spot to enjoy brunch regardless of what you’re craving. Let’s be honest, how can you say no to a place that serves up a chocolate tower French toast?


photo by Jennifer Kathryn 

Beer, pork and oysters? After a long day trekking around the city, we’d say yes to all of the above. Publican is a restaurant that serves up fresh, farmhouse fare in a simple, no-frills way. Not a place for small or delicate plates, Publican serves up hearty, delicious foods in a rustic atmosphere that will have you feeling at ease from the moment you walk in. Food that is this good, and yet this unpretentious is hard to find, but Publican defies the odds.

Pump Room

photo by Jennifer Kathryn 

Located in the Public Hotel, Pump Room houses a relaxed vibe, and more importantly, a lot of great food. Regional flavors and fresh ingredients are highlighted regardless of what meal you’re having there. Late night tapas and small plates as well as brunch time classics like eggs benedict and buttermilk pancakes are all part of the offerings. If you’re there for dinner, the bar makes for a fun spot for after dinner cocktails.


photo by Jennifer Kathryn 

If you’re staying in the Aloft hotel (one of our top hotel picks in Chicago), you’re in luck! Beatrix is actually located in the hotel making it an easy spot to travel to for hotel guests. That being said, it’s still worth the trip even if you’re staying elsewhere. If you’re heading over for brunch, enjoy a great selection of food options along with an amazing variety of coffee drinks showcasing both Intelligentsia and Metropolis coffee roasters. Dinner patrons will enjoy a variety of options there from escarole and potato ravioli to skirt steak. A great cocktail and wine list means you’ll definitely have something good to wash your meal down with.


Drinks With the Girls 

RM Champagne

photo by Jennifer Kathryn 

Located in the West Loop, this is a perfect stop for any wine lover visiting the city. Known for sparkling wine, RM Champagne has a French inspired menu with $1 oysters on Tuesday! Wash your French fare down with a glass of one of their amazing wines or champagnes. As if the evening couldn’t get any better, top your meal off with one of their specialty French desserts—a perfect evening with the ladies.

Lost Lake
The tropics and Chicago don’t necessarily go together but when it comes to Lost Lake, it all makes sense. Lost Lake is a tiki bar on the border of Logan Square and Avondale that serves up some of our favorite tiki cocktails in the city. You and your crew can partake in one of their shared cocktail bowls or order drinks of your own, depending on what you’re in the mood for. And the American-Chinese restaurant next door delivers food right to your table!

The Allis at Soho House

photo by Jennifer Kathryn 

Wanting just a coffee and a cold-pressed juice? After dinner cocktails? The Allis delivers all of the above. Very rarely will you find a place that can do morning pastries and lattes as well as it does evening cocktails, but Allis is one of the rare few. Our recommendation is to head over for a cocktail or two after a long day exploring the city. A beautiful interior, and a prime location inside the exclusive Soho House are just the icing on the cake.

J Parker

photo by Jennifer Kathryn 

For an undeniably beautiful view of Chicago, head to the J Parker, perched on the top floor of the Hotel Lincoln. The drinks aren’t the cheapest, we admit, but the view and ambiance make it worth the splurge (you’re on vacation, after all!). They have a selection of small plates as well, but the real stand-out (in addition to the view) are their cocktails. Head over after dinner for a relaxed but stylish atmosphere, and an Instagram-worthy view of the skyline.

Half Acre
Beer aficionados will feel right at home at Half Acre in Chicago. Home to a brewery and a tap room, Half Acre is a good option whether you want to take a tour or just sample some brews. If you head over on a Saturday, you can get a tour plus a sampling for just $10 (keep in mind that it’s cash only though!). Throughout the year, Half Acre also hosts a number of different events (summer barbeque series, anyone?) so be sure to check in before your visit to see what they have planned.

What are your favorite spots in Chicago? Let us know in the comments! 
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