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.
Chicago Architecture Foundation's Architecture River Cruise
Chicago Architecture Foundation Get a nautical view of the city's skyscrapers.
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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

Miss Ricky's is the diner at the Virgin Hotel
Photograph: Courtesy Virgin
Restaurants, American

9–10am: Chicken and waffles at Miss Ricky's

icon-location-pin Loop

Chicago's Virgin Hotel is located near the heart of the Loop and within walking distance of the Magnificent Mile. Start your day at the hotel's in-house diner, Miss Ricky's, where you can dine on decadent chicken and waffles or a stack of pancakes. Breakfast is served all day, so you can always come back for more.

Things to do

10–10:45am: Conquer the Ledge at the Willis Tower Skydeck

icon-location-pin Loop

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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Attractions, Parks and gardens

11–11:45am: Chill out in Millennium Park

icon-location-pin 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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Restaurants, Hot dogs

1:45–2:30pm: Eat a Chicago-style hot dog at Portillo's

icon-location-pin River North

Head to River North and eat lunch at this über-efficient local chain, which offers authentic Chicago dogs. The juicy dog comes on poppyseed bun steamed to perfect softness and with a generous helping of thick-cut tomatoes, onions and a hefty pickle slice.

WrigleyField.venue.jpg
Photograph: Stephen Green
Sports and fitness, Baseball & softball

3–5pm: Cheer on the Cubs at Wrigley Field

icon-location-pin Wrigleyville

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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Shopping, Shopping centers

5:30–6pm: Go shopping at Water Tower Place

icon-location-pin Streeterville

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.

Gino's East
Photograph: jpellgen / Flickr
Restaurants, Pizza

6–8pm: Dig into some deep dish pizza at Gino's East

icon-location-pin Streeterville

Once you've worked up an appetite, walk down the street and get some deep-dish pizza at this Chicago institution. You'll probably want to order an appetizer while you wait for your gooey pile of cheese, sauce and topping to cook.

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Comedy, Comedy clubs

8–10:30pm: See rising comedic stars on the main stage at Second City

icon-location-pin Lincoln Park

Even if you know nothing about improv, chances are you've heard of Second City. This is the place that put both sketch and improvised comedy on the map while launching the careers of Tina Fey, Chris Farley and John Belushi. Make reservations for a main stage show and you could see the next great Chicago comic.

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TheOriginalMothers.venue.jpg
Photograph: Mark Wright
Music, Music venues

1–4am: Show off your pipes at the Original Mother’s

icon-location-pin Gold Coast

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.

Hotels, Boutique hotels

4:30am: Crash at the Virgin Hotel

icon-location-pin 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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