14 days in Chicago & Colorado Itinerary

14 days in Chicago & Colorado Itinerary

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Route & dates

14 days in Chicago & Colorado Itinerary

Start: Springfield
Drive:  3​h
1
Chicago
— 3 nights
Fly + taxi:  4​h 45​min
2
Steamboat Springs
— 2 nights
Drive:  2​h 45​min
3
Glenwood Springs
— 3 nights
Drive:  2​h 45​min
4
Buena Vista
— 1 night
Drive:  2​h 15​min
5
Colorado Springs
— 1 night
Fly:  4​h 15​min
6
Durango
— 3 nights
Fly:  7​h
End: Springfield

3
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Kids will appreciate attractions like Silver Beach County Park and Museum of Science and Industry. Take a break from the city and head to Grand Mere State Park and Whihala Beach Co Park. And it doesn't end there: admire the masterpieces at The Art Institute of Chicago, see the interesting displays at The Field Museum, admire the striking features of Chicago Cultural Center, and admire nature's wide array of creatures at Shedd Aquarium.

To see maps, ratings, traveler tips, and more tourist information, go to the Chicago route planner .

Springfield to Chicago is an approximately 3-hour combination of flight and subway. You can also drive; or do a combination of bus and train. In September, plan for daily highs up to 78°F, and evening lows to 61°F. Finish your sightseeing early on the 3rd (Wed) so you can travel to Steamboat Springs.

Things to do in Chicago

Museums Parks Outdoors

Side Trips

Grand Mere State Park, Whihala Beach, Silver Beach County Park
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Silver Beach County Park ©
Silver Beach County Park
Museum of Science and Industry ©
Museum of Science and Industry

2
nights
Steamboat Springs

Steamboat Springs ©
An internationally known ski resort, Steamboat Springs sits in the shadow of Mount Werner in north central Colorado.
On the 4th (Thu), explore the world behind art at Steamboat Art Museum, then take in the natural beauty of Strawberry Park Hot Springs, and then admire the sheer force of Fish Creek Falls. Get ready for a full day of sightseeing on the 5th (Fri): explore and take pictures at Steamboat Ski Resort, then get engrossed in the history at Tread of Pioneers Museum, and then tour the pleasant surroundings at Yampa River Botanic Park.

For other places to visit, more things to do, photos, and more tourist information, read Steamboat Springs trip itinerary maker website .

You can do a combination of flight and taxi from Chicago to Steamboat Springs in 5 hours. Alternatively, you can drive; or do a combination of train and bus. The time zone changes from Central Standard Time (CST) to Mountain Standard Time (MST), which is usually a -1 hour difference. Traveling from Chicago in October, expect Steamboat Springs to be slightly colder, temps between 59°F and 30°F. Finish your sightseeing early on the 5th (Fri) so you can drive to Glenwood Springs.

Things to do in Steamboat Springs

Parks Outdoors Winter Sports
Highlights from your plan
Fish Creek Falls ©
Fish Creek Falls
Steamboat Ski Resort ©
Steamboat Ski Resort
Yampa River Botanic Park ©
Yampa River Botanic Park

3
nights
Glenwood Springs

Glenwood Springs ©
Glenwood Springs occupies a scenic location at the junction of the Colorado River and the Roaring Fork River, halfway between Vail and Aspen along the Front Range of the Rocky Mountains.
Explore hidden gems such as River Rafting & Tubing and Hanging Lake. Step out of the city life by going to Hanging Lake Trail and Glenwood Canyon Bike Trail. Pack the 6th (Sat) with family-friendly diversions at Glenwood Caverns Adventure Park. There's more to do: tour the pleasant surroundings at Grizzly Creek Trail.

To see reviews, photos, where to stay, and more tourist information, you can read our Glenwood Springs driving holiday planning site .

Drive from Steamboat Springs to Glenwood Springs in 3 hours. Alternatively, you can do a combination of bus and train; or take a bus. Expect slightly colder weather when traveling from Steamboat Springs in October: highs in Glenwood Springs hover around 47°F, while lows dip to 32°F. Wrap up your sightseeing on the 8th (Mon) early enough to drive to Buena Vista.

Things to do in Glenwood Springs

Outdoors Parks Trails
Highlights from your plan
Hanging Lake Trail ©
Hanging Lake Trail
River Rafting & Tubing
Glenwood Canyon Bike Trail ©
Glenwood Canyon Bike Trail

1
night
Buena Vista

The Town of Buena Vista is a Statutory Town in Chaffee County, Colorado, United States. On the 9th (Tue), take an in-depth tour of Buena Vista Heritage Museum, then relax in the rural setting at Jumpin' Good Goat Dairy, and then relax and float downstream with a rafting and tubing tour.

To see where to stay, maps, more things to do, and other tourist information, you can read our Buena Vista journey tool .

Traveling by car from Glenwood Springs to Buena Vista takes 3 hours. Alternatively, you can do a combination of bus and car; or take a bus. When traveling from Glenwood Springs in October, plan for somewhat warmer days in Buena Vista, with highs around 62°F, while nights are about the same with lows around 31°F. Finish your sightseeing early on the 9th (Tue) to allow enough time to drive to Colorado Springs.

Things to do in Buena Vista

Adventure Tours Outdoors
Highlights from your plan
Climbing Tours
Buena Vista Heritage Museum ©
Buena Vista Heritage Museum
Jumpin' Good Goat Dairy ©
Jumpin' Good Goat Dairy

1
night
Colorado Springs

Colorado Springs ©
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.
On the 10th (Wed), appreciate the extensive heritage of Old Colorado City Historic District, identify plant and animal life at Garden of the Gods, and then take in the dramatic natural features at Red Rock Canyon.

To find traveler tips, more things to do, where to stay, and more tourist information, go to the Colorado Springs tour itinerary maker site .

Drive from Buena Vista to Colorado Springs in 2.5 hours. Alternatively, you can take a bus; or take a bus. Plan for a bit warmer nights when traveling from Buena Vista in October since evenings lows in Colorado Springs dip to 39°F. Wrap up your sightseeing on the 10th (Wed) early enough to travel to Durango.

Things to do in Colorado Springs

Parks Nature Neighborhoods
Highlights from your plan
Garden of the Gods ©
Garden of the Gods
Red Rock Canyon Open Space ©
Red Rock Canyon Open Space
Old Colorado City ©
Old Colorado City

3
nights
Durango

Durango ©
Originally a frontier mining town, Durango is known today for its scenic setting, outdoor activities, and the 1880s steam-powered railway that takes visitors through sections of the mountains where roads don't reach.
Eschew the tourist crowds and head to Balcony House and Spruce Tree House. Chapin Mesa Archeological Museum and Earthen Vessel Gallery will appeal to museum buffs. When in Durango, make a side trip to see Cliff Palace in Mesa Verde National Park, approximately 1h 20 min away. There's much more to do: relax and float downstream with a rafting and tubing tour, stop by Animas Chocolate Company, and tour the pleasant surroundings at Animas River Trail.

To see reviews, where to stay, and other tourist information, refer to the Durango trip planning site .

Traveling by flight from Colorado Springs to Durango takes 4.5 hours. Alternatively, you can do a combination of shuttle and flight; or drive. Traveling from Colorado Springs in October, Durango is a bit cooler at night with lows of 32°F. On the 13th (Sat), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Durango

Outdoors Historic Sites Adventure

Side Trip

Mesa Verde National Park
Highlights from your plan
Cliff Palace ©
Cliff Palace
Balcony House ©
Balcony House
Spruce Tree House ©
Spruce Tree House

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