3 Days in Chicago: Suggested Itineraries
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.
I highly recommend this tour! Great way to see 2 neighborhoods, sample authentic Chicago eats and get a real feel for the city. Our tour guide Martha was terrific! First stop is a Jewish deli where we each got half a Reuben sandwich. Second stop was a slice of deep dish Chicago style pizza at Lou Malnati's. Delish!! We were all full by then! Rest of the tastings were smaller, but also great. Martha also included lots of interesting history about the area.
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This is a must-do tour for anyone visiting Chicago for the first time. We hopped off/on 3 times: once for lunch, once for the Sear's Tower and once for Millenium Park. Highly recommend!
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For our one day in Chicago, we got a great overview of the history and the sites.
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3 Days in Chicago: Suggested Itineraries Written by Viator
Chicago Architecture Guide Written by Viator
Grab a Slice of Chicago-Style Pizza Written by Viator
