$34 Cheap flight deals from Chicago (CHI) to Aspen (DEN)

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This Weekend's Flight Deals from Chicago to Aspen

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Jun 29 - Sat, Jul 5
MDW
Midway Intl.
DEN
Denver Intl.
$174 Roundtrip, found 5 hours ago
$174
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sun, Jun 29 from Midway Intl. to Denver Intl., returning Sat, Jul 5, priced at $174 found 5 hours ago
Sat, Jun 28 - Sun, Jun 29
ORD
O'Hare Intl.
DEN
Denver Intl.
$217 Roundtrip, just found
$217
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to Denver Intl., returning Sun, Jun 29, priced at $217 just found
Sat, Jun 28 - Tue, Jul 15
ORD
O'Hare Intl.
ASE
Pitkin County
$534 Roundtrip, found 1 hour ago
$534
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to Pitkin County, returning Tue, Jul 15, priced at $534 found 1 hour ago
Sat, Jun 28 - Thu, Jul 3
ORD
O'Hare Intl.
EGE
Eagle County Regional
$684 Roundtrip, found 1 day ago
$684
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to Eagle County Regional, returning Thu, Jul 3, priced at $684 found 1 day ago

Airfares from $34 One Way, $68 Round Trip from Chicago to Aspen

Prices starting at $68 for return flights and $34 for one-way flights to Aspen were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Sep 23 - Wed, Sep 24
ORD
Chicago
DEN
Denver
$68 Roundtrip, just found
$68
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Sep 23 from Chicago to Denver, returning Wed, Sep 24, priced at $68 just found
Sat, Jul 12 - Sat, Jul 19
MDW
Chicago
DEN
Denver
$69 Roundtrip, found 5 hours ago
$69
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sat, Jul 12 from Chicago to Denver, returning Sat, Jul 19, priced at $69 found 5 hours ago
Thu, Oct 23 - Tue, Oct 28
ORD
Chicago
DEN
Denver
$157 Roundtrip, just found
$157
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Oct 23 from Chicago to Denver, returning Tue, Oct 28, priced at $157 just found
Wed, Oct 22 - Mon, Oct 27
ORD
Chicago
DEN
Denver
$163 Roundtrip, just found
$163
Roundtrip
just found
Select United flight, departing Wed, Oct 22 from Chicago to Denver, returning Mon, Oct 27, priced at $163 just found
Wed, Oct 22 - Mon, Oct 27
ORD
Chicago
DEN
Denver
$163 Roundtrip, just found
$163
Roundtrip
just found
Select American Airlines flight, departing Wed, Oct 22 from Chicago to Denver, returning Mon, Oct 27, priced at $163 just found

Aspen economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at The Ranahan
4.0-star property

Hyatt Vacation Club at The Ranahan

9.4/10 Exceptional! (1,387 reviews)

Aug 13 - Aug 20

7 night stay

Chicago (ORD) to Denver (DEN)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 3 hours ago
Great place with mountain and river views 3-4 miles from the Breckenridge Town center. They have a few shuttle to the town. We were able to walk one way and then get the shuttle the other way, which was nice. The walk was mostly along the river. The rooms were very comfortable with a kitchenette, sitting room and bedroom, though sitting room has no windows for natural light. Nice big screens in both rooms. They do not serve any free breakfast and nothing hot, though there is a bar for drinks and bar food.

Reviewed on Jun 11, 2025

Timbers and Lone Eagle by Keystone Resort
4.0-star property

Timbers and Lone Eagle by Keystone Resort

9/10 Wonderful! (51 reviews)

Jul 27 - Aug 3

7 night stay

Chicago (ORD) to Denver (DEN)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 6 hours ago
Skiing. Great. Accommodating. C- And this was lone eagle. 3029 unit - checked in with vomit smell on carpet. Bed as hard as a Rock. Ski lockers keys didn’t work. No towels in master bath. Had to replace empty toilet tissue (not end of world but the point). My bet is poor house cleaning stafff too busy trying to clean up vomit from previous guest to get to the rest of the condo. I did mention the smell, right?

Reviewed on Nov 28, 2017

The Maven Hotel at Dairy Block
4.0-star property

The Maven Hotel at Dairy Block

9.4/10 Exceptional! (1,094 reviews)

Jul 31 - Aug 3

3 night stay

Chicago (CHI) to Denver (DEN)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Great vibe. Unique.

Reviewed on Oct 27, 2024

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More About Flying To Aspen from Chicago

Route Information for Flights from Chicago to Aspen

Origin Airport IATA Code
CHI
Destination Airport IATA Code
DEN
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Aspen

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.