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Chicago, United States · 3 days itinerary

Chicago: Architecture & Deep Dish

Photo by Christopher Alvarenga on Unsplash

This three-day trip takes in Chicago's architecture highlights. It starts downtown with Millennium Park, the Art Institute, and a river cruise to establish the city's layout. The next day covers the skyline from Willis Tower and the Board of Trade, then moves north to Lincoln Park and Graceland Cemetery.

3 daysArchitectureRiver cruiseSkydeckLincoln ParkBy travli· Checked by the travli team, September 2026

Day by day

Day 1

Millennium Park and River Cruise

  1. 9:00Millennium ParkSight
  2. 10:15Art Institute of ChicagoSight
  3. 14:00Chicago Cultural CenterSight
  4. 15:30Chicago Architecture Center River CruiseChicago Architecture CenterDay trip
Day 2

Willis Tower and Riverwalk

  1. 9:00Willis TowerSight
  2. 11:45Chicago RiverwalkChicago RiverwalkWalk
  3. 13:00Chicago Board of Trade BuildingSight
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Day 3

Lincoln Park and Graceland Cemetery

  1. 9:00Lincoln Park Zoo & ConservatoryLincoln Park ZooSight
  2. 13:45The Green Mill Cocktail LoungeThe Green MillSight
  3. 15:00Graceland CemeteryWalk
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Chicago questions

Do I need to book the Chicago Architecture Center River Cruise ahead?

Yes. Reserve timed tickets online at least one day before. Expect to pay about 50 dollars per adult.

Are advance tickets required for the Willis Tower Skydeck?

Buy Skydeck tickets online for a timed slot to skip the longest lines. Adult prices vary by date and time, so check the official site for today's rate.

How do I get around Chicago using public transit?

Use CTA trains and buses with a Ventra card. A single ride costs 2.50 dollars and covers most downtown and north side stops.

Do I need reservations for the Art Institute of Chicago?

Buy Art Institute tickets online to skip the queue. Adult admission is higher for non-Chicago residents, so check the museum's site for the current price.

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