Chicago RECOMMENDATIONS See all

3 Days in Chicago

By Viator, August 2018

5 3652 Reviews | Add your review

From skyscrapers to museums to vibrant neighborhoods to public parks, Chicago has something for everyone, and three days is more than enough time to explore its highlights. Travel by bus, bike, or on foot; linger in the bustling Loop; or head out of town on a day trip. Here’s how to plan your 3-day Windy City itinerary.
 
Day 1: Chicago’s Top Attractions
Explore Chicago’s most popular landmarks, many of which are concentrated in the Loop neighborhood, including Millenium Park and the Willis Tower Skydeck. Bus and bicycle tours of the area make it possible to see more in less time, while a hop-on hop-off bus itinerary offers a seamless overview of the city (plus the chance to disembark where and when you wish). Alternatively, combine your Loop adventures with a trip to another part of town. Catch an afternoon Cubs game at Wrigley Field on the North Side, or head to the South Side to explore Chinatown.
 
Day 2: Museums, Architecture, and Other Historical Highlights
Learn about Chicago’s past on an architecture tour—hop aboard a riverboat and cruise all three branches of the Chicago River, spotting highlights such as the Tribute Tower and the Merchandise Mart as you go, or head off on an intimate walking tour to view landmarks firsthand. Then, delve into Chicago’s esteemed museums, including the Field Museum of Natural History, Museum of Science and Industry, and the Art Institute of Chicago.
 
Day 3: Chicago Area Day Trip
Frank Lloyd Wright, a longtime Chicago resident and one of the 20th century’s most celebrated architects, designed a number of buildings in the Chicago area. Discover some of his best-known works on a day trip to the Frank Lloyd Wright Home and Studio in Oak Park, a village located just beyond Chicago’s western edge. Here you'll discover where the architect lived and worked for the first two decades of his career, and where he developed his signature Prairie School style. Oak Park’s other architectural gems include the Frank Lloyd Wright Historic District, Unity Temple, and the Arthur B. Heurtley House.

Tours & Tickets

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Chicago Architecture River Cruise, Chicago, null
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Chicago Architecture River Cruise

5 star rating: Highly Recommended 2438 Reviews

Experience one of the world’s most beautiful cities on a 75-minute cruise on the historic Chicago River. On this architecture cruise, head down the main branch ...  Read more

Location: Chicago, Illinois
Duration: 75 minutes (approx.)

From USD $41.44
Chicago Grand Tour and Admission to 360 Chicago (formerly John Hancock Observatory), Chicago, Day ... 
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Chicago Grand Tour and Admission to 360 Chicago (formerly John Hancock Observatory)

3.5 star rating: Worth doing 79 Reviews

Take a tour of Chicago and visit the 360 Chicago (John Hancock Observatory)! This comprehensive half-day tour is the perfect introduction to the Windy City. ...  Read more

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

From USD $65.00
Skydeck Chicago Admission, Chicago, Bus & Minivan Tours
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Skydeck Chicago Admission

4.5 star rating: Recommended 590 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 $22.00
$24.00 Save $2.00
Chicago Grand Half-Day Tour, Chicago, Attraction Tickets
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Chicago Grand Half-Day Tour

4 star rating: Recommended 333 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 $49.95
Chicago Explorer Pass, Chicago, Bus & Minivan Tours
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Chicago Explorer Pass

4.5 star rating: Recommended 168 Reviews

Create your own sightseeing itinerary with the Chicago Explorer Pass, saving up to 42% on ticket prices. This multi-attraction pass, valid for 30 days after ...  Read more

Location: Chicago, Illinois
Duration: Varies

From USD $75.00
Chicago Lakefront and Museum Campus Segway Tour, Chicago, Sightseeing Passes
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Chicago Lakefront and Museum Campus Segway Tour

5 star rating: Highly Recommended 10 Reviews

Looking for fun things to do in Chicago? Look no further - Explore Chicago with one of our professional guides on this scenic 7 or 8 mile Chicago Segway tour. ...  Read more

Location: Chicago, Illinois
Duration: 2 hours (approx.)

From USD $68.67
Museum of Science and Industry Chicago, Chicago, Segway Tours
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Museum of Science and Industry Chicago

4.5 star rating: Recommended 7 Reviews

The Museum of Science and Industry Chicago is the largest science museum in the country.  Housed in the only remaining building from the 1893 World’s Fair, ...  Read more

Location: Chicago, Illinois
Duration: Flexible

From USD $19.95
City Sightseeing Chicago Hop On Hop Off Tour, Chicago, Museum Tickets & Passes
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City Sightseeing Chicago Hop On Hop Off Tour

5 star rating: Highly Recommended 3 Reviews

Hop-on to a City Sightseeing Chicago bus tour and discover the many amazing, popular landmarks and attractions that are located here. With a 1, 2 or 3 day bus ...  Read more

Location: Chicago, Illinois
Duration: 1 to 3 days

From USD $37.00
Chicago South Side Tour with Optional River Cruise, Chicago, Hop-on Hop-off Tours
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Chicago South Side Tour with Optional River Cruise

4 star rating: Recommended 7 Reviews

Experience the beauty of Chicago on a tour full of history and excitement. See all of the city’s highlights, such as Grant Park, the Adler Planetarium and the ...  Read more

Location: Chicago, Illinois
Duration: 2 hours (approx.)

From USD $31.95
Small-Group Chicago Food Tour: Chinatown, Chicago, Bus & Minivan Tours
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Small-Group Chicago Food Tour: Chinatown

5 star rating: Highly Recommended 5 Reviews

Sample traditional Chinese flavors on this three-hour walking tour through one of the oldest Chinatown neighborhoods in America. Your local guide navigates you ...  Read more

Location: Chicago, Illinois
Duration: 3 hours 25 minutes (approx.)

From USD $60.00

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