Headed to Chicago next month and would love all of your recommendations! I'm looking for your favorite bookstores, local coffee shops, must-see views, great restaurants, and small businesses for a little shopping :)

Question

katie · Answer

the center of order and experimentation: great coffee with a side of stationery and some deadstock vintage clothing

Claire · Answer

Used Books, Coffee, Pastries: Metric coffee and/or Milli by Metric; Myopic Books and Perpetual Books for used and new books. Mindy’s Bakery for savory and sweet down the street from Myopic. Had an insane creamed spinach Stromboli there the other day.

Leslie · Answer

Kasama: One of those places that absolutely lives up to the hype. Go for brunch and definitely load up on the pastries

Maura · Answer

Logan Square: Hop off the Blue Line at Logan, put your name in at Lula for lunch, then pop over to City Lit Books while you wait. After lunch you’re within walking distance of cute shops along Milwaukee, or (my personal favorite) a stroll along the Boulevard. You can head NW for pastries at Loaf Lounge (home of The Bear’s chocolate cake), or the best cocktails at Billy Sunday. Head South on California and you’ll land near Lobo for pizza, fried chicken at Parson’s, Tex-Mex at Lonesome Rose, or drinking chocolate at Katherine Anne’s. You can’t go wrong!

Annie Pontarelli · Answer

Buddy: Buddy is in the Chicago Cultural Center and focuses on local artists, makers and small businesses. A fun stop after checking out the Cultural Center (which is free!)
Buddy is a shop, a hub for making connections between friends we have and those we have yet to meet. We are committed to giving artists and small manufacturers in Chicago a place to showcase and sell their goods and artworks to a vast audience of Chicagoans and visitors at the Chicago Cultural Center.

Valerie Chin · Answer

Chicago Magic Lounge 🪄: The speakeasy bar features close up magic that you can enjoy while you have a drink, but the shows are also a blast

Jennifer Quail · Answer

Chicago: CAC River Cruise aboard First Lady: The river cruise hosted by the Chicago Architecture Center is beyond amazing. It’s like taking a MasterClass while floating through the center of the city’s beautifuL built world.

Seimi · Answer

Pequod's Pizza - Deep Dish Pizza in Chicago: Deep dish pizza is it's own thing. And I think you should go for it if you're in town! There are so many great places: Lou Malnati's, Giordano's, and Gino's East --- but I'm here to recommend Pequod's. It's served in a sizzling pan dish with delicious caramelized cheese and so worth the calories.

Laurel · Answer

The Center for Order and Experimentation: The best eclectic boutique with fine stationery, local foods, small-batch scents, ceramics, etc. plus a great cafe.

rory · Answer

open orchestra rehearsal at millennium park: my favorite event in Chicago, magical

Hannah M. Wilde · Answer

Ca Phe Da: Speaking of which, the Vietnamese iced coffee.

Hannah M. Wilde · Answer

The up room at the Robey House: I don’t even drink much, but if you want to feel very fancy and like you’re in on a secret, take the elevator all the way up, get a cocktail, take in the views!

Hannah M. Wilde · Answer

Cafe Jumping Bean: While you’re in Pilsen, you must stop here! The Molletes are the perfect vegetarian light lunch

Hannah M. Wilde · Answer

Dove’s Luncheonette: Right off the wicker park blue line stoop, great spot for eating solo, everything is delicious!

Hannah M. Wilde · Answer

Dark matter coffee: The best coffee plus every coffee shop is a work of art.

Hannah M. Wilde · Answer

Pilsen community books: Gorgeous inside, excellent zines, curated mix of new and used books. PLUS right across the street from Hai Sou/Ca Phe Da where you should really get a Vietnamese iced coffee

Courtney · Answer

Shaw's Crab House: As a Chicago native, I would highly recommend Shaw’s crab house. It’s an institution. Vibes like no other. One side is a more casual oyster bar that feels untouched by time. The other side is more formal dining. Highly recommend requesting a booth. And the bar seating is also excellent. Perfect martinis. Impeccable service. A great reintroduction to the adults you were before you had kids.

Haley James · Answer

Ummo: "Contemporary Italian" — the food was INCREDIBLE and the space was beautiful. (One of my favorite espresso martinis of all time.)

Rachel Z · Answer

Lula Cafe for breakfast,lunch or dinner! Cindy's rooftop has the best view and delicious cocktails and food.Wicker Park is a great neighborhood for shopping with tons of small boutiques (Eskell), bookstores (Myopic), record stores (Reckless Records), and tons of good food

sunset strip mall · Answer

the national museum of mexican art: a really special, well-curated collection – i love how they've painted the walls to complement the artworks exhibited here

Megan · Answer

Small Cheval: Old-school burgers on a casual patio can’t miss.

Megan · Answer

Barnes & Noble Wicker Park: Yes it’s a Barnes & Noble but it’s beautiful inside. Plus there’s so much around it in Wicker Park to explore!

Megan · Answer

Metric Coffee: Best matcha in the city IMHO!

Kate · Answer

57th Street Books: South Side/Hyde Park. Then can walk to sister bookstore, the Seminary Co-op (next door to Robie House—perfect itinerary pairing!), to browse larger selection of academic and leisure reading.

Julie Gainer · Answer

chicago river walk:  Another one … can you tell I like walking next to water? This is more fun in the evening. stunning views and plenty of stops along the way to grab a snack or a drink.

Julie Gainer · Answer

lakefront path chicago: Walking the lakefront path in summer is so good… bring a suit and jump in at one of them cities many beaches … the views are fabulous

Jodie Resendiz · Answer

parachute hi-fi: You can make a reservation or go on Friday night at 5-5:15 pm (that’s correct) and sit at the bar. Great food and atmosphere!

Jodie Resendiz · Answer

lula cafe: An absolute must!

kitty · Answer

Pizza Lobo, Chicago: Amazing pizza and vibes!!! Had a cameo in The Bear as well!

Chandra Ram · Answer

I wrote a piece for Saveur about some of the restaurants that make Chicago a great food city! Here's the link: https://www.saveur.com/travel/best-restaurants-chicago/: A list of the best/most fun restaurants in Chicago

Cool Your Jets · Answer

Center for order and experimentation: Perfectly curated home goods shop with a cafe, the best spot to snag something uniquely Chicago.

Sarah · Answer

Frank Lloyd Wright Home & Studio Tour: You should check out frank Lloyd wright's home and studio in Oak Park (inner ring suburb adjacent to the city to the west, on the green and blue lines). Take the tour, and then walk around the neighborhood and check out the 25 FLW houses around town, many right around the home and studio. Also walking distance from Broken Tart, a truly incredible coffee shop and bakery. If you go thurs - Saturday, get the espresso cardamom bun.

Megan P · Answer

loba pastry + coffee: I will always get a pineapple sourdough muffin and emmie (essentially a sesame canélé in the shape of a bundt) then whatever other special items I want. I’m also extremely partial to the white chocolate curry scone. The baristas are so nice and the interior is so warm. I love it here! Everyone I take here always wants to come back.

Maryn · Answer

Monteverde: Unreal Italian restaurant. It’s very popular though, so reserve in advance!

Maryn · Answer

architectural boat tour: A must!!

James Kylstra · Answer

Hoosier Mama Pies: Great pie + coffee and homey atmosphere in Ukrainian Village. We try to go here whenever we get back to town. Check out the back patio if the weather’s nice