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

S M T W T F S
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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 Frank Lloyd Wright Home and Studio 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, make a trip to Buckingham Fountain, admire the striking features of Marquette Building, and take in panoramic vistas at Skydeck Chicago - Willis Tower.

For photos, reviews, other places to visit, and more tourist information, read our Chicago trip itinerary app.

Use the Route module to see travel options from your home to Chicago. In May, daily temperatures in Chicago can reach 71°F, while at night they dip to 52°F. Wrap up your sightseeing on the 9th (Sun) early enough to fly to Colorado Springs.

Things to do in Chicago

Museums · Historic Sites · Shopping · Childrens Museums

Side Trip

Find places to stay May 7 — 9:

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 tour the pleasant surroundings 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

Find places to stay May 9 — 11:

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