#30. Route 66
- Rating: 4.5/5 (1,256 reviews)
- Address: 198 South Michigan Ave. Chicago, Illinois
- Read more on Tripadvisor

"For those who are lost, there will always be cities that feel like home," Simon Van Booy wrote in his 2011 novel "Everything Beautiful Began After," and what better way to find the cities that might feel like home than to get lost? Travel beckons, and there are many great cities to explore in the U.S. From New York to Los Angeles, Chicago to Miami, and Las Vegas to San Francisco, metro regions in the U.S. offer an incredible range of activities, attractions, and cultural monuments to enjoy.
Every city has its own unique history—stories of industry, immigration, and imagination. Plus, each city offers its own geographical specificity: San Francisco's gorgeous heights and quad-killing hills; the bustling boroughs of New York and how they wind around bodies of water; the flat desert of Las Vegas with its tremendous, wide-open sky (try stargazing at the nearby Red Rock Canyon for awe-inspiring views of the heavens).
Each city also has its own flavor. Some metros are practically a Baskin-Robbins of adventure, featuring all kinds of flavors, some of which might be complex, unfamiliar, or even new. Los Angeles, for example, can be experienced in so many ways, from its history as the motion picture and entertainment capital to its modern incarnation as one of the most culturally diverse cities in the world—there are many versions of LA to visit, just as there are many iterations of San Francisco, New York, and Las Vegas. Cities, after you scratch the surface, reveal even more treasures within—but first, you must know where to begin!
Stacker compiled a list of the highest-rated things to do in Chicago using data from Tripadvisor. Tripadvisor ranks places using a combination of metrics, including overall rating, reviews, and number of page views. As a result, an activity with a 5 out of 5 overall rating might rank lower than one with a 4 out of 5. Data is as of May 31, 2024.
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- Rating: 4.5/5 (1,256 reviews)
- Address: 198 South Michigan Ave. Chicago, Illinois
- Read more on Tripadvisor
- Rating: 5/5 (744 reviews)
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- Rating: 4.5/5 (1,263 reviews)
- Read more on Tripadvisor
- Rating: 4.5/5 (794 reviews)
- Address: 2391 North Stockton Drive Chicago, Illinois
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- Rating: 4.5/5 (1,204 reviews)
- Address: 1601 North Clark St. Chicago, Illinois
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- Rating: 4.5/5 (874 reviews)
- Address: 500-5700 North Lake Shore Drive Chicago, Illinois
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- Rating: 5/5 (437 reviews)
- Address: 180 North Michigan Ave. 2nd Floor Chicago, Illinois
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- Rating: 4.5/5 (1,116 reviews)
- Address: 735 North State St. Chicago, Illinois
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- Rating: 4.5/5 (2,450 reviews)
- Address: 540 North Lake Shore Drive Chicago, Illinois
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- Rating: 4.5/5 (1,511 reviews)
- Address: 1901 West Madison St. Chicago, Illinois
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- Rating: 4.5/5 (862 reviews)
- Address: 300 North Central Park Ave. Chicago, Illinois
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- Rating: 4/5 (9,909 reviews)
- Address: 1200 S. Lake Shore Drive Chicago, Illinois
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- Rating: 4.5/5 (3,427 reviews)
- Address: 301 S. Columbus Dr. Chicago, Illinois
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- Rating: 4/5 (15,172 reviews)
- Address: 600 East Grand Ave. Chicago, Illinois
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- Rating: 4.5/5 (1,478 reviews)
- Address: 40 East Erie St. Chicago, Illinois
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- Rating: 4.5/5 (2,031 reviews)
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- Rating: 5/5 (724 reviews)
- Address: 177 North State St. Chicago, Illinois
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- Rating: 4.5/5 (3,067 reviews)
- Address: 78 East Washington St. Chicago, Illinois
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- Rating: 4.5/5 (5,983 reviews)
- Address: 2001 North Clark St. Chicago, Illinois
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- Rating: 4.5/5 (3,107 reviews)
- Address: E. Lower Wacker Dr. Chicago, Illinois
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- Rating: 4.5/5 (11,126 reviews)
- Address: 875 North Michigan Ave. 94th Floor Chicago, Illinois
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- Rating: 4.5/5 (8,957 reviews)
- Address: 1400 South Lake Shore Drive Chicago, Illinois
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- Rating: 4.5/5 (18,287 reviews)
- Address: 201 E. Randolph St. Millenium Park Chicago, Illinois
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- Rating: 4.5/5 (9,954 reviews)
- Address: 1060 W. Addison St. Chicago, Illinois
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- Rating: 4.5/5 (17,882 reviews)
- Address: 233 South Wacker Drive entrance on Jackson Blvd. (south side of building) Chicago, Illinois
- Read more on Tripadvisor
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- Rating: 4.5/5 (15,804 reviews)
- Address: North Michigan Ave. Chicago, Illinois
- Read more on Tripadvisor
- Rating: 4.5/5 (11,213 reviews)
- Address: 5700 S. Lake Shore Drive Chicago, Illinois
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- Rating: 5/5 (3,425 reviews)
- Address: 111 East Wacker Drive Chicago, Illinois
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- Rating: 4.5/5 (25,150 reviews)
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- Rating: 5/5 (24,586 reviews)
- Address: 111 South Michigan Ave. Chicago, Illinois
- Read more on Tripadvisor
This story features data reporting by Karim Noorani, writing by Andrea Richards, and is part of a series utilizing data automation across 100 metros.
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