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Photograph: Neal O'Bryan

How to spend 12 hours in Chicago

Only here for a day? Explore some of Chicago’s best dining, drinking and cultural offerings with the help of our guide.

Samantha Nelson
Written by
Samantha Nelson
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Let’s be real: You could spend 12 years in Chicago without having a chance to fully explore the ins and outs of its 77 neighborhoods. But try not to get overwhelmed if you’re here for a quick visit, because you can still get a taste of some of the city’s best food, drinks and attractions so long as you plan ahead. The key to spending your time well is to avoid too much in transit, so we’ve centered the itinerary around the most iconic spots in downtown Chicago with a few detours to just get a taste of the city’s North and West Sides. Make your 12 hours in Chicago count by filling your eyes and stomach and then start planning your next trip to experience more.

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How to spend 12 hours in Chicago

  • Restaurants
  • Filipino
  • East Village
  • price 2 of 4

Start your day in West Town at one of the best restaurants in Chicago. The first Filipino restaurant in the world to earn a Michelin Star, Kasama serves a 13-course tasting menu for dinner that books up more than a month in advance, but their counter-service breakfast is first come, first served. Order your food to go or be prepared to wait in line for a longanisa sausage breakfast sandwich, an ube latte and a wide selection of pastries like blueberry tarts with chamomile cream and coconut black sesame macarons.

  • Museums
  • Science and technology
  • Museum Campus
  • price 2 of 4

It’s easy to spend all day or even a weekend exploring the myriad of exhibits at this natural history museum, which launched in the aftermath of the 1893 World’s Columbian Exposition and now boasts a  collection of 40 million artifacts and specimens. Marvel at Maximo the Titanosaur, the largest dinosaur ever found, and then visit the Field’s most famous resident, SUE the T. Rex, the biggest and most intact fossil of its kind. After you’ve had your fill of science, step outside and visit Kim and Carlo’s Hot Dog Cart for a traditional Chicago-style dog.

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  • Attractions
  • Parks and gardens
  • Millennium Park

Chicago’s motto is “city in a garden,” and urban planners prioritized green spaces after it was rebuilt following the Great Chicago Fire. Millennium Park is a modern embodiment of that vision, a gathering place that hosts concerts, festivals, film screenings, ice skating, art tours and more. See the city skyline and your own face reflected in Cloud Gate—the giant sculpture nicknamed “The Bean”—and the faces of Chicago citizens on 50-foot towers flanking Crown Fountain.

  • Things to do
  • Streeterville
  • price 2 of 4

Get a spectacular view of the city from 1,000 feet up in the building formerly known at the John Hancock Center. The recently renovated 94th floor observatory allows you to look out at Lake Michigan, Navy Pier, the Loop’s skyscrapers and beyond, with the windows providing labels to explain what neighborhoods are in view. Grab a local beer at the brand new Cloud Bar to brace yourself for Tilt, a ride that creates the sensation of tipping over the edge of the building. You can also try some of the city’s most popular snacks like Garrett Popcorn.

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  • Bars
  • Lounges
  • West Loop
  • price 3 of 4

Alinea is Chicago’s most acclaimed restaurant, but chef Grant Achatz’s multi-hour tasting menu experience won’t work on a tight schedule. Instead you can check out sibling spot The Aviary, which applies the same focus on surprising diners with whimsical and meticulously crafted dishes to its complex cocktails. Order a la carte drinks and bites or book a sampling of dishes paired with some of their greatest hits, which can incorporate fire, smoke and elaborate glassware.

  • Comedy
  • Comedy clubs
  • Lincoln Park
  • price 2 of 4

The Second City has served as a training ground for some of the best comedians and comedy writers in the world for more than 60 years, with famous alumni including Stephen Colbert, Bob Odenkirk and Keegan Michael Key. While the improv and sketch comedy group has satellite theaters and touring shows, you shouldn’t miss the chance to check out the original. The performances are often interactive, with actors seeking prompts from the audience or even bringing them on stage, and they’re filled with audacious musical numbers mocking everything from politics to pop culture to the pitfalls of dating.

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  • Music
  • Folk, country and blues
  • Sheffield & DePaul
  • price 1 of 4

The Great Migration brought the blues to Chicago and the music developed its own style in the city, where it has been nurtured by clubs, festivals and local record labels. Open since 1968, Kingston Mines is the largest and oldest continuously operating blues club in Chicago. It boasts two stages, so you can be sure to find an act that matches your vibe. The club is open until 4am Thursday and Friday and 5am Saturday, so there’s time to catch a show no matter what else you have on your itinerary.

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