Chicago is one of our favorite cities, and this list has all our go-to spots for anyone planning a trip. We’ve included the iconic sights, must-visit food stops, and a few hidden gems that locals love. Whether it’s your first time or you’re looking f...
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Eat
Inventive small plates. Don't miss the goat empanadas.
Girl & The Goat
Chic, popular cocktail bar.
The Violet Hour
Near the University of Chicago, this bakery and restaurant has the best milkshakes. Get the Mexicana. Thank me later.
Medici on 57th
The original “farm to table” spot in Chicago; if you go for breakfast, get the breakfast burrito (they can make it gluten-free with corn tortillas too!).
Lula Cafe
Retro vibes, delicious ice cream for a sunny Chicago day.
Lickity Split
Amazing views and great brunch from the top of the Chicago Athletic Association.
Cindy's
I was blown away by Daisies. Amazing food, and they are so gluten-free friendly! Seriously, I can't stop dreaming about the chocolate bar I had for dessert.
Daisies
Don't miss these killer tacos.
Antique Taco
For the wine lovers.
Red and White Wines
Natural wine bar with great small bites.
Outside Voices
If you love gin, here's the place to be.
Scofflaw
This traditional English-style pub has an excellent food program and has even earned a Bib Gourmand designation from Michelin. A savory pie is an absolute must!
Pleasant House Pub
If you love tiki drinks, Three Dots and a Dash is THE cocktail bar for you. The atmosphere is sexy, the service is incredible, and the drinks are divine. As with all tiki drinks, be careful - the alcohol content is always higher than you think. If yo...
Three Dots and a Dash
This speakeasy-style bar serves up some seriously unique cocktails. Every drink is themed around childhood school memories, and the menu is written in old composition notebooks. The service is incredible, and the space is intimate—perfect for a date ...
The Meadowlark
My husband, who is South Indian, was so excited to see a restaurant serving food from his home state of Kerala. He said eating here felt like being home. The fish curry was incredible.
Thattu
From Top Chef winner Joe Flamm comes this delicious, family-style restaurant. Serving up Croatian-Italian fare, it’s a great option for those who enjoy sharing plates—you get to taste a bit of everything.
Rose Mary
Play
You absolutely cannot miss the architectural boat tour - and the best one is with the Chicago Architecture Center.
Chicago Architecture Center River Cruise
Grab a bike and ride along the water. A truly perfect summer day.
Divvy Bikes
Which beach is the best is hotly debated, but can you really go wrong?
Chicago Beaches | Guide to Local Beaches on Lake Michigan
An independent bookstore in Hyde Park with one of the largest collections of academics books in the world.
Seminary Co-op Bookstores
The summer music and film series really can't be beat.
Jay Pritzker Pavilion | Millennium Park Foundation
One of the world's premiere art museums. You can't miss it.
The Art Institute of Chicago
Get in your laughs at The Second City.
The Second City
If you love midcentury vintage design (like me), you MUST stop by Design 329—a vintage design collective in Chicago's Chinatown. This warehouse is home to over 10 vintage design shops, and you could easily spend an entire afternoon getting lost in th...
Design at 329
This bookstore is INCREDIBLE. I did some serious damage to my bank account.
Exile in Bookville
Unabridged Bookstore has been serving the Chicago community since the 1980s. They have an extensive collection, including entire sections dedicated to the LGBTQ+ community.
Unabridged Bookstore
If you have littles, RoscoeBooks is a great option—half of the store is dedicated to children's books!
RoscoeBooks
80,000+ books in this used book paradise.
Myopic Books
Stay
In the heart of Logan Square, they have six guest rooms located above their restaurant and bar. (Bring ear plugs in case you're sensitive to noise.) Starting at only $125/night.
Longman & Eagle
Iconic for a reason.
Chicago Athletic Association
Glorious art deco architecture is going to have swooning at this downtown boutique hotel. The service is incredible and the location is prime.
