Chicago Itinerary: 2 to 5 days, day by day

Skyscrapers along the river, a lakefront to walk, and deep-dish pizza before the blues. Pick a trip length to see every day written out — what to do, where to stay and what it costs.

Every trip length

Pick how long you have in Chicago.

Each one is a complete plan. Here is the shape of each, a line per day.

3 days in Chicago

Day 1Chicago River, Loop landmarks and the lakefront
Day 2Museum Campus and South Loop
Day 3Neighborhood markets, Lincoln Park and a final downtown evening

4 days in Chicago

Day 1Downtown orientation and the lakefront
Day 2Parks, lakefront and museum campus
Day 3Architecture, neighborhoods and classic Chicago food
Day 4Neighborhood color and an easy final downtown stretch

5 days in Chicago

Day 1Downtown Chicago and the riverfront
Day 2Museum Campus and lakefront Chicago
Day 3Historic core, architecture, and West Loop food
Day 4Lincoln Park, neighborhood streets, and local shopping
Day 5Gold Coast, Oak Street, and final downtown views

How many days do you need in Chicago?

4 days is the right length for a first trip to Chicago. That covers the Loop's architecture and a river cruise, the Art Institute, Millennium Park and a night of live blues. With fewer days you see the highlights at a brisk pace; with more, add a day trip to Milwaukee or the Indiana Dunes.

See the 4-day Chicago itinerary →

When to go, what a trip costs and what other travellers planned: Chicago travel guide →

Ready when you are