Explore trips
North America · Single base · 2 NIGHTS
Chicago weekend · Art Institute and Millennium Park
Build a short break around one main visit
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US Letter · 11 × 8.5 in · Landscape
Chicago weekend · Art Institute and Millennium Park
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Day 1
Chicago
America/Chicago- Check in or drop your bags Staypineapple, An Iconic Hotel, The Loop, Chicago
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Walk the Chicago Riverwalk near State Street
Chicago Riverwalk, Chicago
Treat the walk as optional on a late arrival or in poor weather.
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Walk around the Chicago Cultural Center and Millennium Park
Chicago Cultural Center, Chicago
If the Cultural Center is open, take a short look inside. Save the Art Institute for its own day.
- Dinner in the Loop Chicago Loop, Chicago
OvernightStaypineapple, An Iconic Hotel, The LoopChicago -
Day 2
Chicago
America/Chicago- Breakfast near Millennium Park Millennium Park, Chicago
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Walk Millennium Park and see Cloud Gate
Millennium Park, Chicago
Use the park first, then check your museum's public opening time.
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Pick two or three Art Institute collections
Art Institute of Chicago, Chicago
Choose the museum's public entry hours and check for any special exhibition time slots.
- Lunch near Michigan Avenue South Michigan Avenue, Chicago
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Walk Grant Park toward Buckingham Fountain
Grant Park, Chicago
The grounds and skyline are the focus. Treat fountain operation as seasonal.
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Explore the lakeside paths near Monroe Harbor
Monroe Harbor, Chicago
Turn back early if the waterfront is windy or crowded.
- Dinner around South Loop South Loop, Chicago
OvernightStaypineapple, An Iconic Hotel, The LoopChicago -
Day 3
Chicago
America/Chicago- Breakfast near the hotel Chicago Loop, Chicago
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Take a short walk around Daley Plaza or the Riverwalk
Daley Plaza, Chicago
Pick one route and leave it optional.
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Check out and collect bags
Staypineapple, An Iconic Hotel, The Loop, Chicago
Confirm hotel checkout and leave enough time for departure.