Flights from Chicago to Pueblo

Cheapest flights from Chicago

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.

Wed, Oct 15 - Tue, Oct 21

MDW

Midway Intl.

COS

Colorado Springs

$217 Roundtrip, found 4 days ago

$217

Roundtrip

found 4 days ago

Select Delta flight, departing Wed, Oct 15 from Midway Intl. to Colorado Springs, returning Tue, Oct 21, priced at $217 found 4 days ago

Tue, Oct 14 - Tue, Oct 21

MDW

Midway Intl.

COS

Colorado Springs

$268 Roundtrip, found 4 days ago

$268

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Oct 14 from Midway Intl. to Colorado Springs, returning Tue, Oct 21, priced at $268 found 4 days ago

Sat, Oct 18 - Tue, Oct 21

MDW

Midway Intl.

COS

Colorado Springs

$298 Roundtrip, found 4 days ago

$298

Roundtrip

found 4 days ago

Select Delta flight, departing Sat, Oct 18 from Midway Intl. to Colorado Springs, returning Tue, Oct 21, priced at $298 found 4 days ago

Tue, Oct 14 - Sat, Oct 18

MDW

Midway Intl.

COS

Colorado Springs

$319 Roundtrip, found 4 days ago

$319

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Oct 14 from Midway Intl. to Colorado Springs, returning Sat, Oct 18, priced at $319 found 4 days ago

Thu, Oct 16 - Tue, Oct 21

MDW

Midway Intl.

COS

Colorado Springs

$348 Roundtrip, found 4 days ago

$348

Roundtrip

found 4 days ago

Select Delta flight, departing Thu, Oct 16 from Midway Intl. to Colorado Springs, returning Tue, Oct 21, priced at $348 found 4 days ago

Tue, Oct 14 - Fri, Oct 17

MDW

Midway Intl.

COS

Colorado Springs

$349 Roundtrip, found 4 days ago

$349

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Oct 14 from Midway Intl. to Colorado Springs, returning Fri, Oct 17, priced at $349 found 4 days ago

Thu, Oct 16 - Sat, Oct 18

MDW

Midway Intl.

COS

Colorado Springs

$399 Roundtrip, found 4 days ago

$399

Roundtrip

found 4 days ago

Select Delta flight, departing Thu, Oct 16 from Midway Intl. to Colorado Springs, returning Sat, Oct 18, priced at $399 found 4 days ago

Thu, Oct 16 - Fri, Oct 17

MDW

Midway Intl.

COS

Colorado Springs

$429 Roundtrip, found 4 days ago

$429

Roundtrip

found 4 days ago

Select Delta flight, departing Thu, Oct 16 from Midway Intl. to Colorado Springs, returning Fri, Oct 17, priced at $429 found 4 days ago

Wed, Oct 15 - Sun, Oct 19

MDW

Midway Intl.

COS

Colorado Springs

$452 Roundtrip, found 4 days ago

$452

Roundtrip

found 4 days ago

Select Delta flight, departing Wed, Oct 15 from Midway Intl. to Colorado Springs, returning Sun, Oct 19, priced at $452 found 4 days ago

Wed, Oct 15 - Mon, Oct 20

MDW

Midway Intl.

COS

Colorado Springs

$471 Roundtrip, found 4 days ago

$471

Roundtrip

found 4 days ago

Select Delta flight, departing Wed, Oct 15 from Midway Intl. to Colorado Springs, returning Mon, Oct 20, priced at $471 found 4 days ago

Sun, Oct 19 - Tue, Oct 21

MDW

Midway Intl.

COS

Colorado Springs

$488 Roundtrip, found 4 days ago

$488

Roundtrip

found 4 days ago

Select Delta flight, departing Sun, Oct 19 from Midway Intl. to Colorado Springs, returning Tue, Oct 21, priced at $488 found 4 days ago

Tue, Oct 14 - Sun, Oct 19

MDW

Midway Intl.

COS

Colorado Springs

$503 Roundtrip, found 4 days ago

$503

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Oct 14 from Midway Intl. to Colorado Springs, returning Sun, Oct 19, priced at $503 found 4 days ago

Tue, Oct 14 - Mon, Oct 20

MDW

Midway Intl.

COS

Colorado Springs

$522 Roundtrip, found 4 days ago

$522

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Oct 14 from Midway Intl. to Colorado Springs, returning Mon, Oct 20, priced at $522 found 4 days ago

Sat, Oct 18 - Sun, Oct 19

MDW

Midway Intl.

COS

Colorado Springs

$533 Roundtrip, found 4 days ago

$533

Roundtrip

found 4 days ago

Select Delta flight, departing Sat, Oct 18 from Midway Intl. to Colorado Springs, returning Sun, Oct 19, priced at $533 found 4 days ago

Sat, Oct 18 - Mon, Oct 20

MDW

Midway Intl.

COS

Colorado Springs

$552 Roundtrip, found 4 days ago

$552

Roundtrip

found 4 days ago

Select Delta flight, departing Sat, Oct 18 from Midway Intl. to Colorado Springs, returning Mon, Oct 20, priced at $552 found 4 days ago

Thu, Oct 16 - Sun, Oct 19

MDW

Midway Intl.

COS

Colorado Springs

$583 Roundtrip, found 4 days ago

$583

Roundtrip

found 4 days ago

Select Delta flight, departing Thu, Oct 16 from Midway Intl. to Colorado Springs, returning Sun, Oct 19, priced at $583 found 4 days ago

Thu, Oct 16 - Mon, Oct 20

MDW

Midway Intl.

COS

Colorado Springs

$602 Roundtrip, found 4 days ago

$602

Roundtrip

found 4 days ago

Select Delta flight, departing Thu, Oct 16 from Midway Intl. to Colorado Springs, returning Mon, Oct 20, priced at $602 found 4 days ago

Sun, Oct 19 - Mon, Oct 20

MDW

Midway Intl.

COS

Colorado Springs

$739 Roundtrip, found 4 days ago

$739

Roundtrip

found 4 days ago

Select Delta flight, departing Sun, Oct 19 from Midway Intl. to Colorado Springs, returning Mon, Oct 20, priced at $739 found 4 days ago

Fri, Oct 17 - Fri, Oct 17

MDW

Midway Intl.

COS

Colorado Springs

$1,207 Roundtrip, found 4 days ago

$1,207

Roundtrip

found 4 days ago

Select Delta flight, departing Fri, Oct 17 from Midway Intl. to Colorado Springs, returning Fri, Oct 17, priced at $1,207 found 4 days ago

Sun, Oct 19 - Sun, Oct 19

MDW

Midway Intl.

COS

Colorado Springs

$1,759 Roundtrip, found 4 days ago

$1,759

Roundtrip

found 4 days ago

Select Delta flight, departing Sun, Oct 19 from Midway Intl. to Colorado Springs, returning Sun, Oct 19, priced at $1,759 found 4 days ago