On The Roam

United States

Chicago

The best architecture in America, a lakefront you can cycle for miles, and food worth planning around.

Build my Chicago trip

Free, no account needed, about a minute.

Worth
3 days
Cost
Middling
Getting around
Mostly on foot
Currency
USD

Good for

What Chicago rewards you for turning up wanting.

  • Architecture
  • Food
  • Museums
  • Music

And it feels like this

  • city
  • grand
  • water

When to go

Usually at its best in May, June, September and October.

Highlighted months are the ones we would pick. Choose any month to start planning one. The planner reads the real forecast for your dates either way, and moves the indoor days around the rain.

What is actually there

A few of the places we hold in Chicago, in the order the planner rates them. Your days get built from these.

  • Experience

    U-505 Submarine

  • Museum

    Griffin Museum of Science and Industry

  • Café

    Intelligentsia Coffee

  • Restaurant

    The Berghoff Restaurant

  • Historic site

    Our Lady of Sorrows Basilica

  • Park

    Millennium Park

  • Entertainment

    Chicago Theatre

  • Experience

    Frederick C. Robie House

  • Museum

    Chicago History Museum

  • Historic site

    Roberts Temple Church of God in Christ

A day in Chicago

Built by the planner from real places, for nobody in particular. Pick a stop to find it on the map.

© OpenStreetMap contributors

A weekday in Chicago, built from real opening hours and the walk between each stop. Yours would be built around your dates, your pace and the forecast.

You might also like

Places with a similar feel to Chicago.

Ready when you are

Tell us your dates and what you enjoy, and we will have a day for you before you have finished your coffee.

Start planning Chicago

Place data © OpenStreetMap contributors. Prices and opening times change, so it is worth checking official sources before you travel.