Important: This destination may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local, and health advisories for this destination before you book.

Cheap flights from Colorado Springs (DEN) to Chicago (CHI)

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Lowest round trip fares by airline from Colorado Springs and Chicago

Cheapest prices ($40 One Way, $86 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Tue, May 18
DEN
Denver
ORD
Chicago
$40
Frontier Airlines
Fri, Aug 20
DEN
Denver
ORD
Chicago
$43
Spirit Airlines
Tue, May 25
DEN
Denver
ORD
Chicago
$76
American Airlines
Sat, May 15
DEN
Denver
MDW
Chicago
$79
Delta
Fri, Sep 10
COS
Colorado Springs
ORD
Chicago
$79
United
Sat, Aug 21 - Tue, Aug 24
DEN
Denver
ORD
Chicago
$86
Spirit Airlines
Sat, Aug 21 - Tue, Aug 24
DEN
Denver
ORD
Chicago
$87
Spirit Airlines
Tue, May 18 - Tue, May 18
DEN
Denver
ORD
Chicago
$92
United
Wed, May 19 - Wed, May 19
DEN
Denver
ORD
Chicago
$92
American Airlines
Fri, May 21 - Mon, May 24
DEN
Denver
ORD
Chicago
$100
Frontier Airlines

Great Deals On Cheap Hotels in Chicago

Freehand Chicago

Freehand Chicago

3.5 out of 5
19 East Ohio Street, Chicago, IL
The price is $94 per night from May 16 to May 16
Located in River North, this hotel is within a 10-minute walk of Chinese Consulate, Holy Name Cathedral, and Northwestern Memorial Hospital. Museum of Contemporary ...
4.3/5Excellent! (15 reviews)
"I like the bunk beds- so interesting. I love the location. It is close to everything. You are in the heart of the city with lots of activities to do! The staff from day one have been so rude, so cold in attitude just unpleasant but I have tried to beasrespectful and polite as I can possibly be - ..."

Reviewed on Sep 21, 2020

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL
The price is $79 per night from May 16 to May 16
Located in The Loop, this hotel is steps from Columbia College Chicago, Grant Park, and State Street. Art Institute of Chicago and Buckingham Fountain are also ...
3.1/5 (9 reviews)
"I liked the close proximity to downtown, Chicago. The two restaurants on the property as well as close parking in which you would need to pay."

Reviewed on Sep 25, 2020

Travelodge by Wyndham Downtown Chicago
Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave, Elk Grove Village, IL
The price is $40 per night from May 16 to May 16
Situated in Elk Grove Village, this motel is 2.1 mi (3.3 km) from Lake Park and 2.8 mi (4.6 km) from Allstate Arena. Apache Park is 2.9 mi (4.7 km) away.
3.8/5Good! (13 reviews)
"Really nice and clean place. The parking lot was clear."

Reviewed on Feb 23, 2021

Motel 6 Elk Grove Village, IL - O'Hare
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Flights Review

Fly From Colorado Springs to Chicago

Origin Colorado Springs
Destination Chicago
Number of Daily Flights 42
Earliest Flight Departure Date May 20
Latest Flight Departure Date May 21
Popular Airlines Frontier Airlines

Cheap flights from Colorado Springs to Chicago

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Save Even More Time and Money With a Chicago Travel Package

Once your flights are booked, why start all over again searching for a cheap hotel? Book your flight and hotel together, and save yourself more than time and energy. You'll also be able to take advantage of discounts and coupons on your Chicago vacation that you can't get when you book flights and hotel separately.

Relax in Chicago With Confidence and Convenience

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.