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3 Days in Chicago: Suggested Itineraries

By Viator, October 2014

4.5 1210 Reviews | Add your review

There's more to Chicago than can be experienced in three days, but we've got some suggestions to get you started.

Day 1: The City

The Chicago CityPass gives you discounted admission to five of the city's premier attractions: Hancock Observatory, Field Museum, Museum of Science & Industry, Adler Planetarium and Shedd Aquarium. Take your pick of cruises  by water, coach tours by land and exhilarating Segway tours. Or tour Chicago your own way on a Hop-On, Hop-Off Trolley Tour. Get an overview of the city with a comprehensive Grand Half-Day Tour, covering the North Side and South Shore, the Outer Drive, Lincoln Park, Washington Park and Grant Park. Or see the city from the 94th floor of the Hancock Tower.

Day 2: The Architecture

Icons from the famous Chicago School of Architecture are revealed on the Historic Loop Skyscrapers walking tour of Chicago's earliest skyscrapers, built between the 1870s and the 1930s. For contrast, follow up with the Modern Loop Skyscrapers walking tour. Classic Art Deco detailing from the 1920s and 30's is the theme on the Downtown Chicago Deco walking tour.

Day 3: The Outdoors

Start with the Lakefront cycling tour of quiet back streets, city parks, and North Side beaches. Explore more of Chicago's neighborhoods by bike, cycling through the Gold Coast, Old Town, Lincoln Park and Lakeview. Or just hire a bike for the day and plan your own Chicago cycling tour. As the sun sets, take a memorable city lights bike ride. See the sights by water on a river cruise. Take an adrenaline-charged ride in a speedboat across Lake Michigan, or relax into the evening on a romantic dinner cruise. Then take the action indoors on a Chicago Club Crawl.

Tours & Tickets

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Chicago City Hop-on Hop-off Tour

4.5 star rating: Recommended 536 Reviews

See all the sights of Chicago at your own pace! On a Chicago City Hop-on Hop-off Tour you can get off the bus at any scheduled stop to visit Chicago's most ...  Read more

Location: Chicago, Illinois
Duration: Flexible

From USD $35.00

Skydeck Chicago Admission

4.5 star rating: Recommended 224 Reviews

Gaze upon the city sights from the pinnacle of Chicago, the Skydeck. Located on the 103rd floor of Willis Tower, formerly Sears Tower -- the third-tallest ...  Read more

Location: Chicago, Illinois
Duration: Flexible

From USD $18.00

Chicago Crime and Mob Tour

4 star rating: Recommended 66 Reviews

Some of the world’s most notorious criminals, mobsters and gangsters bamboozled their way through Chicago. On this Chicago crime tour, escape into the city’s ...  Read more

Location: Chicago, Illinois
Duration: 90 minutes (approx.)

From USD $39.95

Behind-the-Scenes Chicago Pizza Tour by Coach

5 star rating: Highly Recommended 30 Reviews

Get an exclusive view inside four famous Chicago pizzerias on this 3.5-hour tour and enjoy delicious slices at each! With your small group by mini-coach, go ...  Read more

Location: Chicago, Illinois
Duration: 3 hours 30 minutes (approx.)

From USD $48.00

Chicago City Sights Helicopter Tour

5 star rating: Highly Recommended 9 Reviews

Experience all of Chicago’s best sights from the air on this exciting helicopter tour! Aboard a state-of-the-art helicopter, you'll enjoy a magnificent view of ...  Read more

Location: Chicago, Illinois
Duration: 30 minutes (approx.)

From USD $198.99

Chicago Grand Half-Day Tour

4 star rating: Recommended 155 Reviews

This comprehensive half-day tour of Chicago is the perfect introduction to the Windy City! Discover the highlights of Chicago’s North Side and South Side and ...  Read more

Location: Chicago, Illinois
Duration: 4 hours (approx.)

From USD $48.00

Breakfast in the Sky: Early Access to Skydeck of Willis Tower in Chicago

5 star rating: Highly Recommended 4 Reviews

Start your day with a breathtaking view of Chicago and a hearty breakfast on a glass-enclosed balcony 103 stories up! Ascend to the Skydeck of Willis Tower, ...  Read more

Location: Chicago, Illinois
Duration: 90 minutes (approx.)

From USD $146.99

Chicago Pizza and Beer Tour

4.5 star rating: Recommended 2 Reviews

On this Chicago pizza-tasting tour with a friendly guide, visit four local pizzerias to try Chicago’s famous pizza and relax over cold beer or fine wine. ...  Read more

Location: Chicago, Illinois
Duration: 3.5 hours

From USD $79.99

Viator VIP: Willis Tower Skydeck Early Access, Trolley City Tour and Chicago River Cruise

4 star rating: Recommended 6 Reviews

See classic Chicago sights with this Viator VIP package that includes early entry to the Skydeck in Willis (formerly Sears) Tower where you'll be greeted and ...  Read more

Location: Chicago, Illinois
Duration: 6 hours (approx.)

From USD $124.99

Chicago Prohibition Tour

5 star rating: Highly Recommended 6 Reviews

Discover the underground world of the Prohibition-era speakeasy on an entertaining adults-only tour that takes you to four historic Chicago bars. Learn why the ...  Read more

Location: Chicago, Illinois
Duration: 3 hours 30 minutes (approx.)

From USD $45.00

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