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Chicago's most visited sights sit close together along the lakefront and the river, which makes a first trip unusually easy to plan on foot. This route takes the ten places most visitors start with and groups them by where they are: the Loop and the lakefront first, in walking order, then the two stops that need a train.
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The Loop, on foot
Start here. Millennium Park is free, open from six in the morning until eleven at night, and it holds three of the things people come to Chicago to see: Cloud Gate (the Bean), Crown Fountain, and Frank Gehry's Jay Pritzker Pavilion. Most of the rest of this list is within a twenty-minute walk of this spot.
Next door, with a collection that spans five thousand years. Chicago residents pay a reduced admission with ID. The Modern Wing has its own entrance on Monroe, which is the one to use if the main steps are crowded.
Across Michigan Avenue and free to walk into. It has two stained-glass domes, including the Tiffany dome in Preston Bradley Hall — the largest of its kind anywhere. Ten minutes is enough; twenty is better.
The river
Stop 04
Chicago Riverwalk
The Loop · Along the Chicago River between Lake Shore Drive and Lake Street
A free 1.25-mile path along the south bank of the river's main branch, open six to eleven, built in four stretches with bars, kayak rentals and boat docks along the way. Walk it west from Michigan Avenue; it is the best free thing in the city.
On Wacker at the river, with exhibits on how the city was built — and it is the operator of the architecture river cruise, which is the single best way to understand Chicago in ninety minutes. Book a morning slot the day before.
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 on a busy day. Go early or go late.
The lakefront
A lakefront pier with the Centennial Wheel, the Chicago Children's Museum and boat departures. It is busy and unapologetically touristy, and the view back at the skyline from the end of the pier is worth all of it.
Natural history on the Museum Campus, south of the Loop along the lake, and home to SUE — the most complete Tyrannosaurus rex ever found. If you have walked everything above, this is where the day ends.
The two that need a train
Free admission, no reservation needed, inside Lincoln Park a few miles north of downtown. It is one of the few free zoos left in the country, and it is a good morning on a second day.
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 is not. The Red Line's Addison stop puts you at the gate.
Before you go
Opening hours and admission change through the year, so check each place's own site before you set out. The addresses here were checked against those sites on the date at the top, and the coordinates of the four landmarks with map pins were checked against OpenStreetMap — one of them, Navy Pier, had been 375 metres out on older lists. If something has changed, say so in the comments.
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