5×5: Chicago

All the best hangouts, in all the best cities, from the locals who know… 

With over 2 million residents, Chicago is the third most populous city in the United States. Established in the 1800’s, this concrete jungle has more to offer than historic boat rides and a world-famous baseball park. To learn more about The Windy City, we reached out to five Free People store employees to share with you all — the secrets of Chi-town!!

Danielle Gurley: Senior Store Manager

@daniellegruley + @fpchicago

Asrai Garden – 1935 W North Ave, Chicago, IL 60622

This flower shop is, hands down, my favorite spot in Chicago. Not only does owner, Elizabeth, carry a gorgeous floral selection, but she carries some of the best jewelry, home decor and downright beautiful objects made by local Chicago designers. Tucked away in the vibrant Wicker Park neighborhood, you are guaranteed to walk away with something seemingly handpicked just for you. It’s like a gothic fairytale in a secret garden. The whole staff oozes love and pride for their store and the good vibes are endless. I never leave without a treasure.  @asraigarden

 Skydeck Chicago – 233 S Wacker Dr, 103rd Floor, Chicago, IL 60606 

A touristy attraction for sure, but the breathtaking views are worth it. From the 103rd floor of the Willis Tower (FKA Sears Tower) you can see the entire city of Chicago laid out before you. A clear day will (maybe obviously) yield the best view. Step out on the two glass boxes that jut out of the building to make your stomach drop and get the Instagram shot that will make people go “AH!”

 Garfield Park Conservatory – 300 N. Central Park Ave, Chicago, IL 60624

Ok, so we’re self-admittedly not always the warmest of cities. This is my go-to spot for WARMTH during those long, cold Chicago winters. The fern room and cacti rooms are must-sees. And, if you go during the holiday, check out their floating Christmas tree display– which smells so good it will wipe the Scrooge out of any holiday hater. It’s free to the public and open all year round. I also may be a little partial because my boyfriend proposed to me there just last week!  @gpconservatory

 Logan Square Farmers Market – 3147 W. Logan Blvd. Suite 12, Chicago, IL 60647

OK, let’s talk about SUMMER! This weekly farmers’ market located in the heart of the Logan Square neighborhood is my go-to spot every single Sunday. I stock up on fresh flowers from Windrose Flowers, bread from the local Austrain bakery and meats & cheeses & veggies & fruits…oh my! My BF and I will bring a blanket, make a picnic and people & dog watch for the afternoon. @lsfarmersmarket

Pilsen Neighborhood  – 1831 S Halsted St, Chicago, IL 60608

Three miles southwest of downtown Chicago, this charming neighborhood is chock full of gems, with something for everyone. The main drag, 18th street, boasts some of my favorite Chicago shops & restaurants, with the Shudio carrying amazing vintage & handmade jewelry. Thalia Hall is one of the best music venues in Chicago. Duseks for a fancy cocktail. Verdant Matter for all your houseplant needs. Bowtruss for your daily coffee fix. And you can’t forget the best, cheapest tacos & paletas in the city. @theshudio, @thaliahallchicago, @verdant_matter, @bowtruss

Erin Carter: Wardrobe Stylist with 10 MGMT/Content Creator for @fpchicago

@frisquebusiness @erincarterstyling

A New Leaf – 1645 N Wells St, Chicago, IL 60614

Part flower shop, part event space (they have the dreamiest indoor/outdoor space for weddings and parties), part coolest store I’ve ever walked into. They have everything you can think of… crystals, ribbon, flowers, things for your home, baskets. They have an entire basement filled with candles, painted tiles, buttons… it’s a DIY’ers dream. You walk in and feel creative instantly. It’s also super close to the lake and, if you’re lucky, the Lincoln Park Farmers Market may be in action.

HASH Chicago – 1357 N. Western, Chicago, IL 60622
Hands down my favorite place to get brunch on the weekends. Hash serves the best coffee and breakfast — I get the Truffle Hash, with shredded brussel sprout, kale and carrot topped with truffle aoile..I’m salivating as I type this. Super bright with adorably retro decor and a Grateful Dead Stealie on the front door. It’s my kinda place.

Sprout Home Chicago – 745 N. Damen Avenue, Chicago, IL 60622

Nestled in the Ukrainian Village, Sprout is just a five-minute walk from my house, and I walk that 5 minutes often. They have the prettiest blooms to pick from (I always bring my mom one or two for the mini vase I bought there), the craziest vessels for housing your succulents, plants, or flowers, and they even opened a separate home store across the street. They carry the perfect balance of really, REALLY pretty items and flowers but also offer fun home goods. Not to mention they’re right across the street from my favorite mural in the whole city of Chicago — a big painting of hot dogs and french fries! 

Scone City – 1632 W Division St, Chicago, IL 60622

A modern art gallery and bakery all wrapped into one bright, little space. Everyone who works there is incredibly nice, the artwork is so inspiring to sit around while I’m working, and I wasn’t a scone person until I tried one of theirs.

The Chicago Theatre – 175 N. State Street, Chicago, IL 60601

One of my favorite venues in Chicago to see concerts. I used to live down the street from it, I graduated there, I’m taking my stepmom to see our favorite radio talk show recorded there in January, and the women’s bathroom is very Wes Anderson-y and completely baby pink and weird so that just makes it all the more special.

Brittney Holcomb: Assistant Store Manager/Content Creator for @fpchicago


Heritage Bicycles – 2959 N. Lincoln Ave, Chicago, IL 60657

Heritage General Store. The Free People Chicago girl knows it well. More than that, this is a place to go if you want to see what Chicago is really about. True to the name, the coffee, food and bikes are locally brewed, stirred and built, respectively, right here in Chi-town. Walking in, you may feel for a minute like you’ve stepped back a few eras to a simpler time. There is a typewriter handy on the bar to leave any random notes or quotes you may think up while waiting. If you need some soy milk or half and half, just open up the vintage White Star oven in the corner. I come here for the iced lavender latte and Bang Bang Pie biscuits (another Chicago staple), but I hear the bikes are awesome, too. Anyone can appreciate the vintage beauty of Daisy, their flagship model. 

Mezcaleria Las Flores  3149 W. Logan Blvd, Chicago, IL 60647

Although I pose as a Chicagoan in my day-to-day life, I was once a tried and true desert girl living in Tucson, AZ. Being from Arizona may warrant you a certain snobbery (unavoidable, I’m sorry) when it comes to cactus shopping and what I like to call the desert drinks – tequila and mezcal. When I want to be humbled, I go to Mezcaleria Las Flores. These people know their stuff, and have so much fun telling you about it. The drinks are well thought out and tasty. When you get hungry, you can order anything off the menu at Johnny’s Grill, the diner next door (worth mentioning: they have an all-day breakfast menu). If you want a piece of the Southwest in Chicago, and maybe some fries and a cheeseburger after, go here!

Homeslice 938 W. Webster, Chicago, IL, 60614

Where do I even start? Homeslice has quite the reputation for owning the best patio in Lincoln Park, but the cozy log cabin vibes and great pizza are what get me every time. By log cabin vibes, I mean that the duo best friend owners from Oregon shipped Douglas fir trees to Chicago to construct the space. If you venture outside, you will find additional seating in an Airstream trailer parked out back. I host my birthday pizza party here every year, and I don’t see that changing any time soon.

Lakefront Trail at Lincoln Park  Lakefront Trail, Chicago

There are plenty of iconic pit stops along this 18-mile bike path bordering Lake Michigan, but my jam is the walk from the Fullerton shoreline to North Avenue beach. This path will inch you closer and closer to the skyline until the architectural details start to materialize. The Navy Pier ferris wheel from this view looks nostalgic in the summer, and almost eerie in our colder months. You could walk this path hundreds of times and no two experiences will be the same. Sometimes, you will make it all the way to the Drake on the magnificent mile, and other times you might just turn left and camp out on the beach. If it’s summer, make sure to flag down one of the Popsicle bike carts that frequent the trail, and you will truly be living. 

Lincoln Hall – 2424 N. Lincoln Ave, Chicago, IL 60657

My absolute favorite low-capacity venue in Chicago. The shows here are intimate but super lively, and the artists will always come to the front after for a beer with the crowd. Lincoln Hall is part bar/restaurant with big gymnasium style doors separating the front and back rooms. When those doors open and you walk into the concert hall, the excitement hits you like a ton of bricks (in a good way). My favorite shows to date have been Local Natives, and Cursive’s revival of their Ugly Organ album.

Jacquelyn DeVries: Visual Manager 


Estereo – 2450 N Milwaukee Ave, Chicago, IL 60647

This bar, located in the heart of the ever-chic Logan Square neighborhood, is my go-to spot! Open all day, their bold mix of coffee shop/ bar with a Latin flair makes this spot unique. Whether I want to sip on some Dark Matter coffee or go bold with a watermelon mezcal cocktail, I know their concoctions always hit the spot and the vinyl is always on point! 

Dove’s – 1545 N Damen Ave, Chicago, IL 60622

If you are looking for some grub in the Wicker Park neighborhood, pop in to the not-so typical diner on the corner, Dove’s. This Tex-Mex diner is filled with nostalgic art, great food, friendly service and yummy cocktails. Their “chicken, fried chicken” is not to be missed. Oh, and don’t forget dessert. Ask for the horchta pie (off the menu) and they will know that I sent you! Another hot tip — the jukebox never disappoints. 

The Art Institute of Chicago – 111 S Michigan Ave, Chicago, IL 60603

If you love art, then you must visit the Art Institute of Chicago. One of the world’s largest museums, the Art Institute has a permanent collection of nearly 300,000 works. From Van Gogh to Picasso, Monet to Magritte, Pollock to Basquiat, they have it all. With over 30 special exhibits changing throughout the year, this museum always has something new to explore. The architecture alone is worth soaking in. I spend many days throughout the year visiting the works of the masters, gathering inspiration, and learning!   

The Museum of Contemporary Art – 220 E Chicago Ave, Chicago, IL 60611

Chicago is home to many great museums, another being the Museum of Contemporary Art! Built in 1967, this unique museum holds one of the world’s largest collections of contemporary art. Currently on display is the work of Diana Thater! Her exhibit, The Sympathetic Imagination, presents a series of immersive film and video installations that push the limits of these media to imagine animal experiences in natural habitats. If you are looking for a fun event, check out their late-night series, MCA Prime! 

Myopic Books – 1564 N Milwaukee Ave, Chicago, IL 60622

Hands down the best bookstore in the city. With 3 levels of used books, you are bound to find an arm-full of treasures. This store’s knowledgeable staff is there to guide you through the maze, so don’t be shy to ask for help!  Their music events and poetry readings are always a great time. No photos allowed, so think twice before pulling out your camera! And yes, this store has that great used bookstore smell. 

Meg Tillstrom: Greater Chicago District Manager


Brimfield – 5219 North Clark Street, Chicago, IL, 60640,

There’s nothing quite like this vintage home décor shop to give you all the cozy cabin on the lake feels… for the “Lou” in all of us. A huge wall filled with one-of-a-kind wool blankets, stacks of antique silver trays, piles of pendants from the most obscure places, cozy throw pillows, mid-century furniture, and all your home decorating needs. Holiday here is the most magical time… where else can you can find a whole table full of quirky vintage elf figurines?! With endless displays of the most random trinkets, you’ll never run out of things to explore. They even have an awesome event space upstairs that I dream of booking for something, someday…

Waterfront Café – 6219 N Sheridan Rd, Chicago, IL 60660

This little café is tucked away in the Edgewater neighborhood. Set on Chicago park grounds, it’s barely visible from the road, and one of the only restaurants set steps away from the lake. The most beautiful view overlooking the water, this spot gives off tiki picnic vibes that transport you somewhere much more tropical. Catch live music here on the weekends. A must-visit summer spot for a laid back lunch.

Baker & Nosh – 1303 W Wilson Ave, Chicago, IL 60640

Tucked away in the cutest block of the Uptown neighborhood, this local bakery offers fresh goods and great coffee. I’ve made it a habit to visit every Sunday morning. In the summer, grab a seat in the backyard, kick off your shoes and get lost in a good book. In the winter, I walk over with my pup for a take-out breakfast order of delicious biscuits and gravy for me, and grab a fresh baked dog treat on the way out… she can’t get enough! They even offer baking classes in some seasons.

Mineralogy – 1944 W Montrose Ave, Chicago, IL 60613

The most charming studio shop in the most unexpected place. This tiny studio in the Ravenswood neighborhood has a stunning collection of one-of-a-kind jewelry made with unique natural gems and minerals. Adding to the jewelry collection, this shop has curated a beautiful assortment of candles, crystals, ceramics and wall hangings. On any given day you can find owner and jewelry designer, Theresa, handcrafting from her workbench. She can work with you to design and create your own custom piece!

Lake Michigan, Chicago Sailboat Charters – 400 W Belmont Harbor Dr, Chicago, IL 60657

My absolute favorite way to see the city is by water. Chicago Sailboat Charters will take you out for the day and offer the most amazing views of the skyline. The architecture tour is another great way to see the city. And if you’re on a budget, take a ride on the Chicago water taxi. Any way you cut it, you can’t go wrong. If you get to Chicago in the summer, spring or fall, make sure you find a way to see it by boat.

There you have it, twenty-five Chicago hot spots from vintage boutiques to sailboat rides. With more than enough reasons to head to the land of many lakes, make sure you stop by our Chicago Free People stores, scattered around the city, and say hello to the locals above!!

+ Have Chicago secrets to add? Let us know in the comments below!

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Chicago seems like an awesome place – will have to mark it down for my trip to the US! The observatory looks super awesome. The cacti omg!

Charmaine Ng | Architecture & Lifestyle Blog

5 years ago

Has to be one of the non inclusive representations of Chicago I’ve ever seen. This was tragic

5 years ago

Love this post!

5 years ago

@Andalucia Unfortunately I wouldn’t expect anything else from a brand like this. Gorgeous clothes, beautiful blog posts sometimes, but really, really white.

5 years ago

Oh my gosh. So many gems on here! So glad to see the URBN gals around town!

Check out Architectural Artifacts over in Ravenswood! It makes an adventure of your afternoon

5 years ago

Great city and lots of things to do. Thanks for your sharings. Love them all…

From the natural beauty of the Vienna Woods and Danube River to its beautiful

4 years ago

Can’t wait to hang out in Chicago now! Will be preparing my things and visa as fast as I can. Anyways, could you please suggest the first stop to go?

4 years ago

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4 years ago

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4 years ago

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3 years ago

Amazing shots and nice blog. You’ve emphasize much what to expect in Chicago.

3 years ago

izmir foca otelleri 1887 ile rahat konforlu ve huzurlu bir sekilde bir tatil yapabilirsiniz.