File:Chicago River ferry.jpg: John Picken derivative work: Georgfotoart, CC BY 2.0
Chicago
Chicago is the largest city in Illinois, on the southwest shore of Lake Michigan, with a downtown Loop, Michigan Avenue and a lakefront path.
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Where to stay, by what matters to you
- Places to stay within 10 minutes' walk of the beach in Chicago
- Places to stay with a level walk to the beach in Chicago
- Places to stay in Chicago that work without a car
- Quiet places to stay in Chicago: few bars nearby
- Lively places to stay in Chicago: bars and clubs close by
- Within 30 minutes by car of Field Museum
- Within 30 minutes by car of Navy Pier
- Within 30 minutes by car of Midway International Airport
- Within 30 minutes by car of Museum of Science and Industry
- Within 30 minutes by car of Frederick C. Robie House
- Within 30 minutes by car of O'Hare International Airport
- Within 20 minutes of Cloud Gate (The Bean) and Millennium Park
- Within 20 minutes of 875 North Michigan Avenue (John Hancock Center)
Best things to do in Chicago
The one thing not to miss
Go up the Willis Tower's Skydeck on the 103rd floor, the highest observation deck in the United States, then walk to Millennium Park to see Cloud Gate.
Willis Tower and the Skydeck1. Willis Tower and the Skydeck
A 110-story, 1,451-foot skyscraper in the Loop that opened in 1973 as the world's tallest building. Its Skydeck on the 103rd floor, about 1,353 feet up, is the highest observation deck in the United States and has glass boxes called The Ledge that project from the building.
Tickets are bought online. The Skydeck site does not say advance booking is required. Winter hours listed are 9am to 8pm, until 9pm on Saturday, with last entry 30 minutes before closing. Check the current schedule.
48,770 readers a month
2. Cloud Gate (The Bean) and Millennium Park
Anish Kapoor's polished steel sculpture, made of 168 plates with no visible seams, stands in Millennium Park. The 24.5-acre park opened in July 2004 as part of Grant Park and has public art and outdoor venues.
Millennium Park is a public park; the sources we read do not state opening hours, so check the city's site before you go.
26,660 readers a month
3. Lollapalooza
A four-day music festival held in Grant Park each year. It has run in Chicago since 2005 and is one of the largest music festivals in the world, drawing an estimated 400,000 people.
The festival's site listed 2026 dates of 30 July to 2 August and sells tickets online. We did not find its children's policy, so check before bringing under-18s.
23,688 readers a month
4. Art Institute of Chicago
A private, non-profit art museum in Grant Park, one of the best-known museums in the city.
We could not read the museum's visitor page, so check its own site for opening days and tickets.
10,497 readers a month
Unknown authorUnknown author, Public domain 5. Field Museum
A large natural history museum, one of the largest in the world, known for its educational programmes and collections. It is at 1400 S. DuSable Lake Shore Drive.
The museum site lists daily hours of 9am to 5pm with last entry at 4pm, closed on Thanksgiving and Christmas Day. It does not state whether advance booking is needed, so check its ticket page.
7,551 readers a month
6. Museum of Science and Industry
The Griffin Museum of Science and Industry sits in Jackson Park in Hyde Park, next to Lake Michigan and the University of Chicago.
The museum recommends advance tickets. General admission excludes parking, special exhibits, dome theatre films and tours, which cost extra. Chicago residents get a discount. Check hours on its site.
7,235 readers a month
7. 875 North Michigan Avenue (John Hancock Center)
A 100-story, 1,128-foot skyscraper on the Magnificent Mile, which topped out in 1968 as the second-tallest building in the world. It is the fifth-tallest building in Chicago.
The sources we read do not say whether the building's observation deck is open or how to book it. Check before you go.
6,946 readers a month
8. Grant Park and Buckingham Fountain
A 319-acre park in the Loop that includes Millennium Park, the Art Institute and the Museum Campus. Buckingham Fountain, dedicated in 1927, is one of the largest fountains in the world and runs from about mid-April to mid-October with evening colour-light shows.
The fountain runs generally from mid-April to mid-October, so it is not on in winter.
6,790 readers a month
9. Frederick C. Robie House
A Prairie-style house museum on the University of Chicago campus, designed by Frank Lloyd Wright and completed in 1910. It is described as one of his best Prairie buildings.
The sources we read do not give tour times or booking details. Check before you go.
5,291 readers a month
Sources
10. Navy Pier
A pier about 3,300 feet long that opened in 1916 as Municipal Pier. It has a 196-foot Ferris wheel, the Chicago Children's Museum, the Chicago Shakespeare Theater and summer fireworks on Wednesday and Saturday nights.
Fireworks run Wednesday and Saturday nights in summer and Saturday nights in fall. We did not confirm admission details for the rides and attractions.
4,355 readers a month
Sources
Just missed the list: Shedd Aquarium (11th by readers; a public aquarium opened in 1930); Lincoln Park Zoo (also popular; a free zoo, open every day)
How we ranked these
By how many people read about each place on English Wikipedia in a typical month, measured October 2026. It is a popularity measure, not our opinion. Willis Tower and the Skydeck leads with about 48,770 readers a month. Photos come from Wikimedia Commons under free licences; the author and licence are on each photo.
Research required. Area notes for this destination are not written yet. The top 10 above is sourced; the rest of this page is an outline.
Affiliate disclosure: Booking links on this site are partner links. Once our partnership is active we earn a commission if you book, at no extra cost to you. It does not change what we recommend. How this works.