Flights from Colorado Springs to Chicago

Cheapest flights from Colorado Springs

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Jul 8 - Sun, Jul 13

DEN

Denver Intl.

ORD

O'Hare Intl.

$171 Roundtrip, found 1 day ago

$171

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Tue, Jul 8 from Denver Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $171 found 1 day ago

Sat, Jun 28 - Sat, Jul 5

DEN

Denver Intl.

ORD

O'Hare Intl.

$194 Roundtrip, found 5 days ago

$194

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Sat, Jun 28 from Denver Intl. to O'Hare Intl., returning Sat, Jul 5, priced at $194 found 5 days ago

Tue, Jul 8 - Sun, Jul 13

DEN

Denver Intl.

ORD

O'Hare Intl.

$194 Roundtrip, found 1 day ago

$194

Roundtrip

found 1 day ago

Select American Airlines flight, departing Tue, Jul 8 from Denver Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $194 found 1 day ago

Tue, Jul 8 - Sun, Jul 13

DEN

Denver Intl.

ORD

O'Hare Intl.

$194 Roundtrip, found 1 day ago

$194

Roundtrip

found 1 day ago

Select United flight, departing Tue, Jul 8 from Denver Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $194 found 1 day ago

Tue, Jul 8 - Tue, Jul 15

DEN

Denver Intl.

ORD

O'Hare Intl.

$205 Roundtrip, found 4 days ago

$205

Roundtrip

found 4 days ago

Select American Airlines flight, departing Tue, Jul 8 from Denver Intl. to O'Hare Intl., returning Tue, Jul 15, priced at $205 found 4 days ago

Tue, Jul 8 - Sun, Jul 13

DEN

Denver Intl.

ORD

O'Hare Intl.

$209 Roundtrip, found 1 day ago

$209

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Jul 8 from Denver Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $209 found 1 day ago

Thu, Jul 10 - Sat, Jul 12

DEN

Denver Intl.

ORD

O'Hare Intl.

$213 Roundtrip, found 4 days ago

$213

Roundtrip

found 4 days ago

Select American Airlines flight, departing Thu, Jul 10 from Denver Intl. to O'Hare Intl., returning Sat, Jul 12, priced at $213 found 4 days ago

Thu, Jul 31 - Fri, Aug 8

DEN

Denver Intl.

MDW

Midway Intl.

$216 Roundtrip, found 4 days ago

$216

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Thu, Jul 31 from Denver Intl. to Midway Intl., returning Fri, Aug 8, priced at $216 found 4 days ago

Tue, Jul 29 - Wed, Aug 6

DEN

Denver Intl.

MDW

Midway Intl.

$218 Roundtrip, found 4 days ago

$218

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Jul 29 from Denver Intl. to Midway Intl., returning Wed, Aug 6, priced at $218 found 4 days ago

Wed, Jul 9 - Sun, Jul 13

DEN

Denver Intl.

ORD

O'Hare Intl.

$222 Roundtrip, found 3 days ago

$222

Roundtrip

found 3 days ago

Select United flight, departing Wed, Jul 9 from Denver Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $222 found 3 days ago

Fri, Jul 4 - Fri, Jul 11

DEN

Denver Intl.

ORD

O'Hare Intl.

$229 Roundtrip, found 4 days ago

$229

Roundtrip

found 4 days ago

Select Delta flight, departing Fri, Jul 4 from Denver Intl. to O'Hare Intl., returning Fri, Jul 11, priced at $229 found 4 days ago

Tue, Jul 8 - Sun, Jul 13

DEN

Denver Intl.

ORD

O'Hare Intl.

$229 Roundtrip, found 1 day ago

$229

Roundtrip

found 1 day ago

Select American Airlines flight, departing Tue, Jul 8 from Denver Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $229 found 1 day ago

Sat, Jun 28 - Sat, Jul 5

DEN

Denver Intl.

ORD

O'Hare Intl.

$232 Roundtrip, found 5 days ago

$232

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Sat, Jun 28 from Denver Intl. to O'Hare Intl., returning Sat, Jul 5, priced at $232 found 5 days ago

Thu, Jul 10 - Sun, Jul 13

DEN

Denver Intl.

ORD

O'Hare Intl.

$234 Roundtrip, found 4 days ago

$234

Roundtrip

found 4 days ago

Select American Airlines flight, departing Thu, Jul 10 from Denver Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $234 found 4 days ago

Tue, Jul 8 - Wed, Jul 16

DEN

Denver Intl.

ORD

O'Hare Intl.

$235 Roundtrip, found 5 days ago

$235

Roundtrip

found 5 days ago

Select American Airlines flight, departing Tue, Jul 8 from Denver Intl. to O'Hare Intl., returning Wed, Jul 16, priced at $235 found 5 days ago

Wed, Jul 9 - Sun, Jul 13

DEN

Denver Intl.

ORD

O'Hare Intl.

$240 Roundtrip, found 3 days ago

$240

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Wed, Jul 9 from Denver Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $240 found 3 days ago

Thu, Jul 31 - Fri, Aug 8

DEN

Denver Intl.

MDW

Midway Intl.

$242 Roundtrip, found 4 days ago

$242

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Thu, Jul 31 from Denver Intl. to Midway Intl., returning Fri, Aug 8, priced at $242 found 4 days ago

Tue, Jul 8 - Sun, Jul 13

DEN

Denver Intl.

ORD

O'Hare Intl.

$244 Roundtrip, found 1 day ago

$244

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Jul 8 from Denver Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $244 found 1 day ago

Mon, Nov 24 - Thu, Nov 27

COS

Colorado Springs

ORD

O'Hare Intl.

$301 Roundtrip, found 17 hours ago

$301

Roundtrip

found 17 hours ago

Select Delta flight, departing Mon, Nov 24 from Colorado Springs to O'Hare Intl., returning Thu, Nov 27, priced at $301 found 17 hours ago

Wed, Jul 9 - Sun, Jul 13

DEN

Denver Intl.

ORD

O'Hare Intl.

$355 Roundtrip, found 3 days ago

$355

Roundtrip

found 3 days ago

Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Wed, Jul 9 from Denver Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $355 found 3 days ago