$29 Cheap flight deals from Chicago (CHI) to Cripple Creek (DEN)

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This Weekend's Flight Deals from Chicago to Cripple Creek

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.

Sat, Jan 24 - Sun, Jan 25
ORD
O'Hare Intl.
DEN
Denver Intl.
$254 Roundtrip, found 5 hours ago
$254
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sat, Jan 24 from O'Hare Intl. to Denver Intl., returning Sun, Jan 25, priced at $254 found 5 hours ago
Sun, Jan 25 - Mon, Jan 26
MDW
Midway Intl.
DEN
Denver Intl.
$293 Roundtrip, found 5 hours ago
$293
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sun, Jan 25 from Midway Intl. to Denver Intl., returning Mon, Jan 26, priced at $293 found 5 hours ago
Sun, Jan 25 - Mon, Jan 26
RFD
Greater Rockford
DEN
Denver Intl.
$375 Roundtrip, found 5 hours ago
$375
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Sun, Jan 25 from Greater Rockford to Denver Intl., returning Mon, Jan 26, priced at $375 found 5 hours ago
Sat, Jan 24 - Mon, Jan 26
ORD
O'Hare Intl.
COS
Colorado Springs
$418 Roundtrip, found 9 hours ago
$418
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Sat, Jan 24 from O'Hare Intl. to Colorado Springs, returning Mon, Jan 26, priced at $418 found 9 hours ago

Airfares from $29 One Way, $79 Round Trip from Chicago to Cripple Creek

Prices starting at $79 for return flights and $29 for one-way flights to Cripple Creek were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Mar 12 - Sat, Mar 21
ORD
Chicago
DEN
Denver
$79 Roundtrip, found 4 hours ago
$79
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Thu, Mar 12 from Chicago to Denver, returning Sat, Mar 21, priced at $79 found 4 hours ago
Thu, Feb 5 - Tue, Feb 10
MDW
Chicago
DEN
Denver
$145 Roundtrip, found 3 days ago
$145
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Feb 5 from Chicago to Denver, returning Tue, Feb 10, priced at $145 found 3 days ago
Sat, Feb 14 - Sat, Feb 28
ORD
Chicago
DEN
Denver
$166 Roundtrip, found 17 hours ago
$166
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Sat, Feb 14 from Chicago to Denver, returning Sat, Feb 28, priced at $166 found 17 hours ago
Tue, Mar 17 - Wed, Mar 25
ORD
Chicago
DEN
Denver
$179 Roundtrip, found 3 days ago
$179
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Mar 17 from Chicago to Denver, returning Wed, Mar 25, priced at $179 found 3 days ago
Sat, Feb 21 - Wed, Feb 25
ORD
Chicago
DEN
Denver
$182 Roundtrip, found 3 hours ago
$182
Roundtrip
found 3 hours ago
Select United flight, departing Sat, Feb 21 from Chicago to Denver, returning Wed, Feb 25, priced at $182 found 3 hours ago

Cripple Creek 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

9.6/10 Exceptional! (1,598 reviews)

Mar 5 - Mar 8

3 night stay

Chicago (CHI) to Denver (DEN)

American Airlines • Coach

Denver (DEN) to Chicago (CHI)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,038, price is now $607 per person
$607
per person
found 1 day ago
Staff were excellent. Rooms look like there brand new

Reviewed on Jan 15, 2026

Gold Point Resort Breckenridge by Vacatia
3.0-star property

Gold Point Resort Breckenridge by Vacatia

9.2/10 Wonderful! (111 reviews)

Feb 21 - Feb 27

6 night stay

Chicago (ORD) to Denver (DEN)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,366, price is now $791 per person
$791
per person
found 1 day ago
The place was OK, but I had higher expectations. The view was wonderful, but the condo was just basic and lacking character and dated.

Reviewed on Sep 5, 2023

Embassy Suites by Hilton Denver Downtown Convention Center
4.0-star property

Embassy Suites by Hilton Denver Downtown Convention Center

9/10 Wonderful! (1,319 reviews)

Feb 21 - Mar 1

8 night stay

Chicago (CHI) to Denver (DEN)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,696, price is now $997 per person
$997
per person
found 1 day ago
It was a wonderful stay - great staff, from valet to housekeeping to food services to hospitality.

Reviewed on Dec 2, 2025

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More About Flying To Cripple Creek from Chicago

Route Information for Flights from Chicago to Cripple Creek

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

Chicago to Cripple Creek

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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.