Chicago RECOMMENDATIONS See all

3 Days in Chicago: Suggested Itineraries

By Viator, June 2015

4.5 1825 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 713 Reviews

Location: Chicago, Illinois
Duration: Flexible

From USD $35.00

Skydeck Chicago Admission

4.5 star rating: Recommended 339 Reviews

Location: Chicago, Illinois
Duration: Flexible

From USD $22.00

Behind-the-Scenes Chicago Pizza Tour by Coach

5 star rating: Highly Recommended 58 Reviews

Location: Chicago, Illinois
Duration: 3 hours 30 minutes

From USD $59.99

Chicago Crime and Mob Tour

4.5 star rating: Recommended 158 Reviews

Location: Chicago, Illinois
Duration: 90 minutes

From USD $35.95
$39.95 Save $4.00

Chicago City Sights Helicopter Tour

5 star rating: Highly Recommended 16 Reviews

Location: Chicago, Illinois
Duration: 30 minutes

From USD $198.99

Chicago Grand Half-Day Tour

4 star rating: Recommended 232 Reviews

Location: Chicago, Illinois
Duration: 4 hours

From USD $47.99

Chicago Prohibition Tour

5 star rating: Highly Recommended 35 Reviews

Location: Chicago, Illinois
Duration: 3 hours 30 minutes

From USD $44.99

Chicago Pizza and Beer Tour

5 star rating: Highly Recommended 11 Reviews

Location: Chicago, Illinois
Duration: 3.5 hours

From USD $79.99
From USD $124.00

Small-Group Chicago Food Tour: Gold Coast and Old Town

5 star rating: Highly Recommended 56 Reviews

Location: Chicago, Illinois
Duration: 3 hours

From USD $49.99

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