Flights from Chicago to Aspen

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.

Sat, Sep 6 - Sat, Sep 13

ORD

O'Hare Intl.

DEN

Denver Intl.

$116 Roundtrip, found 1 day ago

$116

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Sat, Sep 6 from O'Hare Intl. to Denver Intl., returning Sat, Sep 13, priced at $116 found 1 day ago

Sun, Sep 21 - Wed, Sep 24

ORD

O'Hare Intl.

DEN

Denver Intl.

$128 Roundtrip, found 18 hours ago

$128

Roundtrip

found 18 hours ago

Select Frontier Airlines flight, departing Sun, Sep 21 from O'Hare Intl. to Denver Intl., returning Wed, Sep 24, priced at $128 found 18 hours ago

Sat, Oct 4 - Wed, Oct 8

ORD

O'Hare Intl.

DEN

Denver Intl.

$129 Roundtrip, found 2 hours ago

$129

Roundtrip

found 2 hours ago

Select Frontier Airlines flight, departing Sat, Oct 4 from O'Hare Intl. to Denver Intl., returning Wed, Oct 8, priced at $129 found 2 hours ago

Sat, Sep 13 - Sun, Sep 14

ORD

O'Hare Intl.

DEN

Denver Intl.

$134 Roundtrip, found 3 days ago

$134

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Sat, Sep 13 from O'Hare Intl. to Denver Intl., returning Sun, Sep 14, priced at $134 found 3 days ago

Thu, Sep 4 - Thu, Sep 11

ORD

O'Hare Intl.

DEN

Denver Intl.

$140 Roundtrip, found 1 day ago

$140

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Thu, Sep 4 from O'Hare Intl. to Denver Intl., returning Thu, Sep 11, priced at $140 found 1 day ago

Wed, Aug 20 - Sun, Aug 24

ORD

O'Hare Intl.

DEN

Denver Intl.

$145 Roundtrip, found 6 days ago

$145

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Wed, Aug 20 from O'Hare Intl. to Denver Intl., returning Sun, Aug 24, priced at $145 found 6 days ago

Sat, Oct 4 - Wed, Oct 8

ORD

O'Hare Intl.

DEN

Denver Intl.

$151 Roundtrip, found 2 hours ago

$151

Roundtrip

found 2 hours ago

Select American Airlines flight, departing Sat, Oct 4 from O'Hare Intl. to Denver Intl., returning Wed, Oct 8, priced at $151 found 2 hours ago

Sat, Oct 4 - Wed, Oct 8

ORD

O'Hare Intl.

DEN

Denver Intl.

$151 Roundtrip, found 2 hours ago

$151

Roundtrip

found 2 hours ago

Select United flight, departing Sat, Oct 4 from O'Hare Intl. to Denver Intl., returning Wed, Oct 8, priced at $151 found 2 hours ago

Tue, Aug 26 - Sat, Aug 30

ORD

O'Hare Intl.

DEN

Denver Intl.

$152 Roundtrip, found 5 days ago

$152

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Tue, Aug 26 from O'Hare Intl. to Denver Intl., returning Sat, Aug 30, priced at $152 found 5 days ago

Sat, Aug 9 - Tue, Aug 12

ORD

O'Hare Intl.

DEN

Denver Intl.

$153 Roundtrip, found 7 hours ago

$153

Roundtrip

found 7 hours ago

Select Frontier Airlines flight, departing Sat, Aug 9 from O'Hare Intl. to Denver Intl., returning Tue, Aug 12, priced at $153 found 7 hours ago

Thu, Sep 4 - Sun, Sep 14

ORD

O'Hare Intl.

DEN

Denver Intl.

$154 Roundtrip, found 1 day ago

$154

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Thu, Sep 4 from O'Hare Intl. to Denver Intl., returning Sun, Sep 14, priced at $154 found 1 day ago

Sat, Oct 4 - Wed, Oct 8

ORD

O'Hare Intl.

DEN

Denver Intl.

$157 Roundtrip, found 2 hours ago

$157

Roundtrip

found 2 hours ago

Select Frontier Airlines flight, departing Sat, Oct 4 from O'Hare Intl. to Denver Intl., returning Wed, Oct 8, priced at $157 found 2 hours ago

Sun, Sep 21 - Wed, Sep 24

ORD

O'Hare Intl.

DEN

Denver Intl.

$160 Roundtrip, found 18 hours ago

$160

Roundtrip

found 18 hours ago

Select Frontier Airlines flight, departing Sun, Sep 21 from O'Hare Intl. to Denver Intl., returning Wed, Sep 24, priced at $160 found 18 hours ago

Sun, Sep 21 - Wed, Sep 24

ORD

O'Hare Intl.

DEN

Denver Intl.

$161 Roundtrip, found 18 hours ago

$161

Roundtrip

found 18 hours ago

Select United flight, departing Sun, Sep 21 from O'Hare Intl. to Denver Intl., returning Wed, Sep 24, priced at $161 found 18 hours ago

Sat, Aug 30 - Sat, Sep 6

ORD

O'Hare Intl.

DEN

Denver Intl.

$161 Roundtrip, found 2 days ago

$161

Roundtrip

found 2 days ago

Select United flight, departing Sat, Aug 30 from O'Hare Intl. to Denver Intl., returning Sat, Sep 6, priced at $161 found 2 days ago

Fri, Aug 8 - Tue, Aug 12

ORD

O'Hare Intl.

DEN

Denver Intl.

$162 Roundtrip, found 7 hours ago

$162

Roundtrip

found 7 hours ago

Select Frontier Airlines flight, departing Fri, Aug 8 from O'Hare Intl. to Denver Intl., returning Tue, Aug 12, priced at $162 found 7 hours ago

Sat, Oct 4 - Wed, Oct 8

ORD

O'Hare Intl.

DEN

Denver Intl.

$164 Roundtrip, found 2 hours ago

$164

Roundtrip

found 2 hours ago

Select United flight, departing Sat, Oct 4 from O'Hare Intl. to Denver Intl., returning Wed, Oct 8, priced at $164 found 2 hours ago

Sun, Sep 28 - Wed, Oct 8

ORD

O'Hare Intl.

DEN

Denver Intl.

$165 Roundtrip, found 9 hours ago

$165

Roundtrip

found 9 hours ago

Select Frontier Airlines flight, departing Sun, Sep 28 from O'Hare Intl. to Denver Intl., returning Wed, Oct 8, priced at $165 found 9 hours ago

Tue, Sep 9 - Thu, Sep 11

ORD

O'Hare Intl.

DEN

Denver Intl.

$168 Roundtrip, found 4 days ago

$168

Roundtrip

found 4 days ago

Select United flight, departing Tue, Sep 9 from O'Hare Intl. to Denver Intl., returning Thu, Sep 11, priced at $168 found 4 days ago

Sat, Aug 16 - Sun, Aug 24

ORD

O'Hare Intl.

DEN

Denver Intl.

$217 Roundtrip, found 1 day ago

$217

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, Aug 16 from O'Hare Intl. to Denver Intl., returning Sun, Aug 24, priced at $217 found 1 day ago