Whether you’re stopping through Chicago on a long layover or driving through on the way to a nearby state, there will definitely be more than enough to keep you busy. Below is a list of how to have a rockin’ time in the Windy City for 24 hours with options depending on what you want to get out of your experience. Despite choosing some touristy things you just can’t miss, I’ve also added a resident-twist to it. 

This post tackles the Loop and River North, the most touristy parts of the city. The Loop is also the business district, so it becomes a ghost town on the weekends and after about 7pm. Look out for future posts on the rest of what this exciting town has to offer!

Morning

Breakfast

Do-Rite Donuts – Not the healthiest or most filling option around, but donuts are a staple breakfast item in Chicago. And Do-Rite does it right. I’m a huge fan of the gluten-free cinnamon & sugar option. I’m not a coffee drinker, but there’s always a line of people waiting to get a cuppa.

Corner Bakery – Need more substance? Like chai latte instead of coffee? Then head next door to Corner Bakery on Randolph St.

10am-12pm: Tour

Free Tours by Foot – City tours are a great way to get a lay of the land somewhere new, and this company offers theirs as pay-what-you-like. To be a true tourist, sign up for the North Loop and Millennium Park Tour and make sure to take pictures of the famous “bean” and the Jay Pritzker Pavilion at the park.

Afternoon

Lunch

Revival Food Hall – With a slew of options, you can’t go wrong with this modern day food court. Personal favorite: Smoque BBQ. Dying to try: Aloha Poke Co.

Cemita’s Puebla – Okay, so technically this isn’t in the Loop per se, but it is the West Loop. The cemitas, or Mexican sandwiches, here are spot on, so I have to include it! Hop on the pink line and grab a pollo cemita made with fresh, authentic ingredients from across the border.

1:30-4:30pm: Art or Shopping

Art Institute of Chicago – Rated the #1 museum in the world, the Art Institute is a must when visiting Chi-town. From Andy Warhol to Degas and Georgia O’Keefe, the works presented here span all styles of artistry.

Magnificent Mile – Arts and museums not really your thing? Go for an afternoon of shopping on the Mag Mile, instead. Make sure to add 3 Arts Club Cafe to your itinerary for an afternoon pick-me-up and tour of beautiful furniture.

Evening

5pm: Dinner and drinks

Havana – Some of the best Cuban food Chicago has to offer can be found at Havana! I highly recommend the Ropa Vieja and it’d be a shame if you didn’t try the coconut mojito.

7-8:30pm: Cruise or Show

Sunset Tour on Wendella Boats – There are a plethora of architecture tours offered here, but the best views of the city are at sunset! The boat is narrated on the river with historical and architectural facts first and then goes out to the lake for stunning sunset pictures.

Broadway in Chicago – Visiting Chicago in the winter? Check out a show and the awesome architecture at the Civic Opera House or Auditorium Theatre, or choose a production at one of the many other theaters the city boasts.

Night

9pm: John Hancock Building

Soak in 360-degree views of the 2nd best skyline in the world at the Hancock’s observation deck, 360 CHICAGO, or while sipping on a cocktail at the Signature Lounge.

11pm: Nightcap

If you’re visiting in summer, choose the rooftop, Cerise, at Virgin Hotel. If the weather’s not so great, the Game Room at Chicago Athletic Association is a great choice.