Chicago trip ideas

Trips planned for Chicago run 3 to 4 days. These are the places they keep coming back to, and the trips themselves, day by day.

  • 2 trips
  • 3 to 4 days
  • 12 places

How many days do you need in Chicago?

2 trips planned for Chicago run 3 to 4 days.

A 3-day planA 4-day plan
Map of the most-visited places in Chicago

What to see in Chicago

The places Chicago trips keep coming back to, most often first.

  1. 1

    Millennium Park

    Public park in Chicago, Illinois, USA.

    In 2 of 2 trips
  2. 2

    Grant Park

    Urban park in Chicago, Illinois, USA.

    In 2 of 2 trips
  3. 3

    Shedd Aquarium

    Public aquarium in Chicago, Illinois, United States.

    In 2 of 2 trips
  4. 4

    Institute for the Study of Ancient Cultures, West Asia & North Africa

    Chicago archaeology museum and research center.

    In 2 of 2 trips
  5. 5

    Kenneth C. Griffin Museum of Science and Industry

    Museum in Chicago, Illinois, United States.

    In 2 of 2 trips
  6. 6

    Basilica of St. Hyacinth

    Church in Chicago, USA.

    In 1 of 2 trips
  7. 7

    Holy Trinity Cathedral

    Cathedral in Chicago, Illinois.

    In 1 of 2 trips
  8. 8

    Biograph Theater

    Theater and former movie theater in Chicago, Illinois, United States.

    In 1 of 2 trips
  9. 9

    Lincoln Park Zoo

    Zoo located in Lincoln Park in Chicago, Illinois.

    In 1 of 2 trips
  10. 10

    Our Lady of Sorrows Basilica

    Catholic church in Chicago.

    In 1 of 2 trips
  11. 11

    Civic Opera House

    Opera house in Chicago, Illinois, United States.

    In 1 of 2 trips
  12. 12

    Chicago Temple Building

    Church building in Chicago, Illinois, United States of America.

    In 1 of 2 trips

Trips to Chicago

Sample tripChicago in 4 Days: Sanctuaries, Stages and LakefrontSacred spaces of several faiths · stages and opera · parks to lakefront museums4 days · September · a solo trip · 16 stopsSample tripChicago in 3 Days: Lakefront, Museums, and South Side3 days · June · lakefront parks, museums, and the South Side3 days · June · a couple's trip · 12 stops

Good to know

Is Lincoln Park Zoo free to visit?

Yes. It is one of the few remaining free zoos in the United States, which makes an unhurried evening visit easy to plan.

Where does this Chicago itinerary spend each day?

Day 1 stays in the northwest-side Polish village and Lincoln Park; Day 2 runs from the West Side through the Loop to the Near North Side; Day 3 is the central parkland; Day 4 covers the South Side around the University of Chicago.

What is the Institute for the Study of Ancient Cultures?

A compact museum on the University of Chicago campus, formerly the Oriental Institute, holding collections from Egypt, Mesopotamia, Persia and beyond. Admission is free.

When is the best time to see the Shedd Aquarium?

This itinerary places it in the evening, when the day-visitor crowds have thinned and the lakefront walk from Grant Park is quiet.

Where is the Obama Presidential Center?

In Jackson Park on Chicago's South Side, a short ride from the Institute for the Study of Ancient Cultures and the Griffin Museum of Science and Industry.

Are Millennium Park and Grant Park connected?

They sit side by side in the same downtown green; Grant Park runs along the lakefront south of Millennium Park, and Shedd Aquarium lies further along the same stretch.

Plan your own Chicago trip

Tell Triptic your dates and who is going, and get the days, real flights and a place to stay.

Plan a Chicago trip