The landmarks most people start with, in a sensible order.
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Chicago's most visited sights sit close together along the lakefront and the river, which makes a first trip easy to plan on foot and by train. This list covers the places most visitors start with, grouped by where they are: the Loop and the lakefront first, then the two stops that need a train ride.
Each entry notes what the place is and where it is. Opening hours and admission change through the year, so check the official site before you go.
Addresses and links on this list were checked against each place's own website on 2026-09-18.
The Loop
Free and open 6am to 11pm, with Cloud Gate (the Bean), Crown Fountain and Frank Gehry's Jay Pritzker Pavilion. Start here — most of the rest of this list is within walking distance.
The Loop
Next door to Millennium Park, with a collection spanning 5,000 years. Chicago residents pay a reduced admission with ID; the Modern Wing has its own entrance on Monroe.
The Loop
Free to walk into, with two stained-glass domes — including the Tiffany dome in Preston Bradley Hall, the largest of its kind anywhere.
The Loop
A free 1.25-mile path along the south bank of the main branch of the river, open 6am to 11pm, built in four stretches with bars, kayak rentals and boat docks along the way.
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The Loop
Exhibits on how the city was built, and the operator of the architecture river cruise — the single best way to understand Chicago in ninety minutes.
The Loop
The 103rd-floor observation deck of Willis Tower, including The Ledge — glass boxes that project out from the side of the building. Expect a queue and about ninety seconds on the glass.
Streeterville
A lakefront pier with the Centennial Wheel, the Chicago Children's Museum and boat departures. Busy, unapologetically touristy, and the view back at the skyline is worth it.
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Museum Campus
Natural history on the Museum Campus, home to SUE the Tyrannosaurus rex — the most complete T. rex ever found.
Lincoln Park
Free admission, no reservation needed, inside Lincoln Park a few miles north of downtown. One of the few free zoos left in the country.
Wrigleyville
Home of the Cubs since 1916 and the second-oldest ballpark in the major leagues. Worth a game if the season is on, and a walk around Wrigleyville if it isn't.
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