$41 Cheap flight deals from Chicago (CHI) to Littleton (DEN)

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This Weekend's Flight Deals from Chicago to Littleton

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, Feb 7 - Tue, Feb 10
ORD
O'Hare Intl.
DEN
Denver Intl.
$244 Roundtrip, found 19 hours ago
$244
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Sat, Feb 7 from O'Hare Intl. to Denver Intl., returning Tue, Feb 10, priced at $244 found 19 hours ago
Fri, Feb 6 - Mon, Feb 9
MDW
Midway Intl.
DEN
Denver Intl.
$259 Roundtrip, found 13 hours ago
$259
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Fri, Feb 6 from Midway Intl. to Denver Intl., returning Mon, Feb 9, priced at $259 found 13 hours ago
Fri, Feb 6 - Mon, Feb 16
RFD
Greater Rockford
DEN
Denver Intl.
$688 Roundtrip, found 1 day ago
$688
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Feb 6 from Greater Rockford to Denver Intl., returning Mon, Feb 16, priced at $688 found 1 day ago

Airfares from $41 One Way, $70 Round Trip from Chicago to Littleton

Prices starting at $70 for return flights and $41 for one-way flights to Littleton were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Apr 4 - Sat, Apr 11
ORD
Chicago
DEN
Denver
$70 Roundtrip, found 22 hours ago
$70
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Sat, Apr 4 from Chicago to Denver, returning Sat, Apr 11, priced at $70 found 22 hours ago
Mon, Feb 23 - Sat, Feb 28
MDW
Chicago
DEN
Denver
$139 Roundtrip, found 3 days ago
$139
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Feb 23 from Chicago to Denver, returning Sat, Feb 28, priced at $139 found 3 days ago
Sat, Mar 14 - Thu, Mar 19
ORD
Chicago
DEN
Denver
$176 Roundtrip, found 1 day ago
$176
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Mar 14 from Chicago to Denver, returning Thu, Mar 19, priced at $176 found 1 day ago
Tue, Mar 3 - Wed, Mar 4
RFD
Rockford
DEN
Denver
$183 Roundtrip, found 3 days ago
$183
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Mar 3 from Rockford to Denver, returning Wed, Mar 4, priced at $183 found 3 days ago
Tue, Apr 28 - Tue, May 5
ORD
Chicago
DEN
Denver
$187 Roundtrip, found 1 hour ago
$187
Roundtrip
found 1 hour ago
Select United flight, departing Tue, Apr 28 from Chicago to Denver, returning Tue, May 5, priced at $187 found 1 hour ago

Littleton 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 12 - Mar 15

3 night stay

Chicago (ORD) to Denver (DEN)

American Airlines • Coach

Denver (DEN) to Chicago (ORD)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,107, price is now $710 per person
$710
per person
found 1 day ago
Staff were excellent. Rooms look like there brand new

Reviewed on Jan 15, 2026

Limelight Hotel Snowmass
4.0-star property

Limelight Hotel Snowmass

9.6/10 Exceptional! (757 reviews)

Mar 13 - Mar 16

3 night stay

Chicago (CHI) to Denver (DEN)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,208, price is now $1,431 per person
$1,431
per person
found 1 day ago
I had a fabulous stay at the property as a last minute booking. Great breakfast buffet in the morning and I was also able to bring my dog. I loved the convenience of Base Village. There is a lot of construction on the lot behind so be prepared to wake up early. Only issue is that I didn’t receive room service nor towels during my stay. Perhaps it’s a standard these days from an environmental standpoint but hadn’t experienced the lack of that service in the Aspen/Snowmass area before. Otherwise, I would definitely stay again.

Reviewed on Jun 25, 2024

Timbers and Lone Eagle by Keystone Resort
4.0-star property

Timbers and Lone Eagle by Keystone Resort

9.2/10 Wonderful! (57 reviews)

Mar 22 - Mar 29

7 night stay

Chicago (ORD) to Denver (DEN)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $8,615, price is now $5,603 per person
$5,603
per person
found 1 day 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

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More About Flying To Littleton from Chicago

Route Information for Flights from Chicago to Littleton

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

Chicago to Littleton

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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.