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

Tue, Jul 8 - Fri, Jul 11

DEN

Denver Intl.

MDW

Midway Intl.

$193 Roundtrip, just found

$193

Roundtrip

just found

Select Delta flight, departing Tue, Jul 8 from Denver Intl. to Midway Intl., returning Fri, Jul 11, priced at $193 just found

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 - Fri, Jul 11

DEN

Denver Intl.

ORD

O'Hare Intl.

$194 Roundtrip, just found

$194

Roundtrip

just found

Select American Airlines flight, departing Tue, Jul 8 from Denver Intl. to O'Hare Intl., returning Fri, Jul 11, priced at $194 just found

Tue, Jul 8 - Fri, Jul 11

DEN

Denver Intl.

ORD

O'Hare Intl.

$194 Roundtrip, just found

$194

Roundtrip

just found

Select United flight, departing Tue, Jul 8 from Denver Intl. to O'Hare Intl., returning Fri, Jul 11, priced at $194 just found

Tue, Jul 8 - Fri, Jul 11

DEN

Denver Intl.

ORD

O'Hare Intl.

$204 Roundtrip, just found

$204

Roundtrip

just found

Select Frontier Airlines flight, departing Tue, Jul 8 from Denver Intl. to O'Hare Intl., returning Fri, Jul 11, priced at $204 just found

Tue, Jul 8 - Tue, Jul 15

DEN

Denver Intl.

ORD

O'Hare Intl.

$205 Roundtrip, found 5 days ago

$205

Roundtrip

found 5 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 5 days ago

Thu, Jun 19 - Sat, Jun 21

DEN

Denver Intl.

ORD

O'Hare Intl.

$208 Roundtrip, found 4 hours ago

$208

Roundtrip

found 4 hours ago

Select Frontier Airlines flight, departing Thu, Jun 19 from Denver Intl. to O'Hare Intl., returning Sat, Jun 21, priced at $208 found 4 hours 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

Tue, Jul 8 - Fri, Jul 11

DEN

Denver Intl.

ORD

O'Hare Intl.

$211 Roundtrip, just found

$211

Roundtrip

just found

Select American Airlines flight, departing Tue, Jul 8 from Denver Intl. to O'Hare Intl., returning Fri, Jul 11, priced at $211 just found

Tue, Jul 8 - Fri, Jul 11

DEN

Denver Intl.

ORD

O'Hare Intl.

$212 Roundtrip, just found

$212

Roundtrip

just found

Select American Airlines flight, departing Tue, Jul 8 from Denver Intl. to O'Hare Intl., returning Fri, Jul 11, priced at $212 just found

Thu, Jul 10 - Sat, Jul 12

DEN

Denver Intl.

ORD

O'Hare Intl.

$213 Roundtrip, found 5 days ago

$213

Roundtrip

found 5 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 5 days ago

Thu, Jul 31 - Fri, Aug 8

DEN

Denver Intl.

MDW

Midway Intl.

$216 Roundtrip, found 5 days ago

$216

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Thu, Jul 31 from Denver Intl. to Midway Intl., returning Fri, Aug 8, priced at $216 found 5 days ago

Tue, Jul 29 - Wed, Aug 6

DEN

Denver Intl.

MDW

Midway Intl.

$218 Roundtrip, found 5 days ago

$218

Roundtrip

found 5 days ago

Select Delta flight, departing Tue, Jul 29 from Denver Intl. to Midway Intl., returning Wed, Aug 6, priced at $218 found 5 days ago

Tue, Jul 8 - Fri, Jul 11

DEN

Denver Intl.

ORD

O'Hare Intl.

$220 Roundtrip, just found

$220

Roundtrip

just found

Select American Airlines flight, departing Tue, Jul 8 from Denver Intl. to O'Hare Intl., returning Fri, Jul 11, priced at $220 just found

Tue, Jul 8 - Fri, Jul 11

DEN

Denver Intl.

ORD

O'Hare Intl.

$222 Roundtrip, just found

$222

Roundtrip

just found

Select United flight, departing Tue, Jul 8 from Denver Intl. to O'Hare Intl., returning Fri, Jul 11, priced at $222 just found

Tue, Jul 8 - Fri, Jul 11

DEN

Denver Intl.

MDW

Midway Intl.

$228 Roundtrip, just found

$228

Roundtrip

just found

Select Delta flight, departing Tue, Jul 8 from Denver Intl. to Midway Intl., returning Fri, Jul 11, priced at $228 just found

Fri, Jun 20 - Sun, Jun 22

DEN

Denver Intl.

ORD

O'Hare Intl.

$228 Roundtrip, found 4 hours ago

$228

Roundtrip

found 4 hours ago

Select Frontier Airlines flight, departing Fri, Jun 20 from Denver Intl. to O'Hare Intl., returning Sun, Jun 22, priced at $228 found 4 hours ago

Mon, Nov 24 - Thu, Nov 27

COS

Colorado Springs

ORD

O'Hare Intl.

$301 Roundtrip, found 1 day ago

$301

Roundtrip

found 1 day ago

Select Delta flight, departing Mon, Nov 24 from Colorado Springs to O'Hare Intl., returning Thu, Nov 27, priced at $301 found 1 day ago

Wed, Jul 9 - Sun, Jul 13

DEN

Denver Intl.

ORD

O'Hare Intl.

$355 Roundtrip, found 4 days ago

$355

Roundtrip

found 4 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 4 days ago