5 days in Chicago & Colorado Springs Itinerary

5 days in Chicago & Colorado Springs Itinerary

Created using Inspirock United States journey planner

Make it your trip
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Chicago
— 2 nights
Fly
2
Colorado Springs
— 2 nights
Fly

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Chicago

— 2 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Visit Frank Lloyd Wright's Unity Temple and Pleasant Home for their historical value. For shopping fun, head to The Magnificent Mile or Ernest Hemingway Birthplace. There's lots more to do: admire the masterpieces at The Art Institute of Chicago, don't miss a visit to Buckingham Fountain, admire the striking features of Marquette Building, and browse the exhibits of Chicago Cultural Center.

To find more things to do, reviews, and more tourist information, read Chicago day trip planning site.

Use the Route module to find travel options from your starting location to Chicago. In May, daily temperatures in Chicago can reach 71°F, while at night they dip to 52°F. Finish up your sightseeing early on the 9th (Sun) so you can catch the flight to Colorado Springs.

Things to do in Chicago

Museums · Historic Sites · Shopping · Neighborhoods

Side Trip

Colorado Springs

— 2 nights
Stunning Garden of the Gods Park scenery, blue skies and the glory of Pikes Peak-America’s Mountain have attracted visitors to Colorado Springs for more than a century.
Start off your visit on the 10th (Mon): stroll around Garden of the Gods, surround yourself with nature on Colorado Wolf Adventures, and then get to know the fascinating history of Old Colorado City. Here are some ideas for day two: take a memorable drive along Pikes Peak - America's Mountain and then identify plant and animal life at Colorado Wolf and Wildlife Center.

Start your trip to Colorado Springs by creating a personalized itinerary on Inspirock.

Fly from Chicago to Colorado Springs in 4.5 hours. Alternatively, you can drive; or do a combination of train and bus. The time zone difference moving from Central Standard Time to Mountain Standard Time is minus 1 hour. Traveling from Chicago in May, Colorado Springs is slightly colder at night with lows of 42°F. Cap off your sightseeing on the 11th (Tue) early enough to catch the flight back home.

Things to do in Colorado Springs

Parks · Outdoors · Wildlife · Scenic Drive

Side Trips