Chicago itineraries
Pick how long you have. Each plan is paced for real life, with lunch breaks, travel estimates and a note on what to book ahead.
1 day
1 day in Chicago
- Day 1: Skydeck Chicago at Willis Tower, Art Institute of Chicago & more
2 days
2 days in Chicago
- Day 1: Skydeck Chicago at Willis Tower, Art Institute of Chicago & more
- Day 2: Millennium Park & Deep-Dish Pizza
3 days
3 days in Chicago
- Day 1: Skydeck Chicago at Willis Tower, Art Institute of Chicago & more
- Day 2: Millennium Park & Deep-Dish Pizza
- Day 3: Explore Chicago
4 days
4 days in Chicago
- Day 1: Skydeck Chicago at Willis Tower, Art Institute of Chicago & more
- Day 2: Millennium Park & Deep-Dish Pizza
- Day 3: Explore Chicago
- Day 4: Explore Chicago
5 days
5 days in Chicago
- Day 1: Skydeck Chicago at Willis Tower, Art Institute of Chicago & more
- Day 2: Millennium Park & Deep-Dish Pizza
- Day 3: Explore Chicago
- Day 4: Explore Chicago
- Day 5: Explore Chicago