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Chicago Architecture FoundationGet a nautical view of the city's skyscrapers.

Your 24-hour itinerary: The Mainstreamer

You can see some famous Chicago sights in a 24-hour window. Just follow the tourists to some of the city's most well known attractions.

Zach Long
Written by
Zach Long
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There's nothing wrong with following the crowd, especially when you're following them to some of the best Chicago attractions. There's a reason that tourists flock to very specific locales in the city: It's because they're fun. It's what Ferris did. With the help of our mainstreamer itinerary, you can experience a Chicago Cubs game, a sketch comedy show and a late-night karaoke bar—all in the span of 24 hours. Whether you're visiting the city of the first time or just want to act like you're new to town, you'll have no trouble blending in with the hordes of Chicago sightseers. Your day starts in the Chicago Loop...

24 hours for the Mainstreamer

10–10:45am: Conquer the Ledge at the Willis Tower Skydeck
  • Things to do
  • Loop
  • price 2 of 4

Journey to the 103rd floor of the Willis Tower and enjoy the view before mustering all of your courage and steping onto the Ledge. The glass cube structure extends over the side of the building, making you feel as if you’re suspended 1,353 feet off the ground. Try not to lose that breakfast.

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11–11:45am: Chill out in Millennium Park
  • Attractions
  • Parks and gardens
  • Millennium Park

Catch a bus to Millennium Park, a 24.5-acre greenspace which features Frank Gehry's Pritzker Pavilion and serpentine bridge; sculptor Anish Kapoor's 110-ton Cloud Gate (a.k.a. “The Bean”); and Jaume Plensa's Crown Fountain, with its ever-changing array of locals' faces spewing water very five minutes in the summer months.

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  • Sports and fitness
  • Baseball & softball
  • Wrigleyville
  • price 1 of 4

Leave the Loop and catch the Red Line to Wrigleyville, the home of historic Wrigley Field. Buy tickets in advance or take your chances with the scalpers lining the streets before entering the Friendly Confines and knocking back an Old Style in the bleachers. If the Cubs aren't in town, you can take your pick of the area's various sports bars.

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5:30–6pm: Go shopping at Water Tower Place
  • Shopping
  • Shopping centers
  • Streeterville
  • price 3 of 4

Head back downtown for a quick stop at Water Tower Place, a mall situated on Michigan Avenue that hosts the usual selection of apparel retailers as well as the American Girl Place and a Lego Store.

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11pm–1am: Get tropical at Three Dots and a Dash
  • Bars
  • Cocktail bars
  • River North
  • price 2 of 4

Chicago may not be a tropical getaway, but you can pretend you're on the beach by paying a visit to River North cocktail bar Three Dots and a Dash. Enjoy a delicious (and strong) cocktail or team up with some friends and sip on a punch bowl.

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  • Music
  • Music venues
  • Gold Coast
  • price 1 of 4

You've got one more stop on your intinerary: Singing and dancing at the Original Mother's. This Division Street bar offers nightly karaoke and a dance floor that is usually packed with late-night revelers. Even if you don't make it to 4am, you can at least sing "Sweet Caroline" before you turn in for the evening.

4:30am: Crash at the Virgin Hotel
  • Hotels
  • Boutique hotels
  • Loop

The new Virgin Hotel is a dream hotel for people into design and technology, with an app to control the room temperature, a pour-over coffee setup in each room and a Tesla to give free rides to guests. The press release about the hotel said the bed “functions as a playpen and traditional bed," so interpret that as you'd like.

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