Let the windy city whisk you away on a spontaneous adventure! Spontaneous and planning, however, they don’t really go hand-in-hand. So, we decided to give you the fun part, and leave the planning to us. If you find yourself lucky enough to have a full 24 hours to spare in Chicago, we’ve got something for you to do every hour, on the hour, plus a map to help you get there.
12PM: BY THE BOOK
Live-music Mondays and poetry readings complement the over 70,000 books available for your reading pleasure at Myopic Books.
1PM: ALL THE FEELS
Ikram‘s dramatic ruby facade can’t be missed. Carve out time to shop high-end designers, have a snack at the cafe, and browse local art.
2PM: MARGARITA MEMOIRS
Is there more to life than queso fundido and a classic margarita on a funky outdoor patio? Find out at Big Star.
3PM: TAKE ME OUT
To the ballgame! A Trip to Chicago would be incomplete without a hotdog in one hand and foam finger on the other at Wrigley Field.
4PM: CEREAL KILLER
If you take snack time seriously, head to The Wormhole Coffee for a bowl of cereal amidst fellow snack aficionados.
5PM: I WANT CANDY
For over 90 years, Margie’s Candies has been serving Chicago’s sweet tooth. Head to this staple for homemade sundaes and hand-dipped candy.
6PM: CAFE CULTURE
Head to the Three Arts Club in Restoration Hardware to check out a showroom of home furnishings and grab a snack at the 3 Arts Club Café.
7PM: A SAUCY SITUATION
There’s something special in the sauce at Gino’s East. Order the deep dish Chi-talian Stallion, you won’t regret it.
8PM: PIG OUT
Cheese, swine + wine. Three words when put together create the magical experience that is The Purple Pig. Ricotta Gnocchi, enough said.
9PM: BOOZY MOVIES
Davis Theater features first-run films alongside a restaurant and bar with 26 beers on tap, all of which can come with you into your movie.
A 5-course cocktail tasting at The Aviary is a Chicago must. These experimental libations are like nothing you’ve ever tasted before.
11PM: DOWN TO DRINK
Pop by The Drifter for a nightcap, a basement bar below Green Door Tavern that can be found in the venue’s old speakeasy section.
12AM: EGGSTRA YUMMY
The delicious chilaquiles at Au Cheval are only served after midnight. If you have an affinity for eggs, you can’t miss this no-frills spot.
1AM: GET LOST
If a hidden tiki bar sounds right up your alley, head to Lost Lake. Glamorous escapism with a side of rum punch for all.
2AM: PAINT THE TOWN RED
Enter the red door at Rossi’s and reveal a secret chamber of late-night vices in what is easily the most unpretentious bar in River North.
3AM: LET’S TACO ‘BOUT IT
Get your fix in between warm tortillas at Velvet Taco. A few blocks away, this small spot serves some of the best late-night eats in town.
4AM: FOOD UNTIL FOUR
Quality isn’t closed at 4am. It lives inside Bijan’s Bistro, where dishes like escargot and roasted duck a l’orange are always an option.
5AM: OFF THE RAILS
What was once an abandoned railway is now The 606, a 2.7 mile trail and recreational park ideal for a sunrise bike ride through the city.
11AM: LET’S FLOW
There’s no better place to flow in Chicago than at Ahimsa Oak Park Yoga, a sacred space to reset during your one night adventure.
7AM: TIME TO TONE
Warm up for a spontaneous day ahead with a full-body, low impact workout at Pure Barre.
There’s no better way to see the city than stand-up paddleboarding along Lake Michigan. Head to Chicago SUP for rentals and lessons!
9AM: A QUIET ZONE
The Harold Washington Library‘s postmodern design features a serene and green atrium on the 9th floor. Pick up a book and get lost in time!
10AM: CONTEMPORARY CREATIVITY
Make your way to The Museum of Contemporary Art. Established in 1967, it is one of the world’s largest contemporary art venues.
11AM: FASHION FIRST
Stop and shop at Seek Vintage, a cozy shop with retro finds featuring a large selection of 1930s to 1980s decor items & clothes.