$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.
MDW
Midway Intl.
DEN
Denver Intl.
$147 Roundtrip, found 21 hours ago
$147
Roundtrip
found 21 hours ago
ORD
O'Hare Intl.
DEN
Denver Intl.
$176 Roundtrip, found 5 hours ago
$176
Roundtrip
found 5 hours ago
RFD
Greater Rockford
DEN
Denver Intl.
$291 Roundtrip, found 3 days ago
$291
Roundtrip
found 3 days ago
ORD
O'Hare Intl.
EGE
Eagle County Regional
$418 Roundtrip, found 3 days ago
$418
Roundtrip
found 3 days 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.
MDW
Chicago
DEN
Denver
$68 Roundtrip, found 4 hours ago
$68
Roundtrip
found 4 hours ago
ORD
Chicago
DEN
Denver
$68 Roundtrip, found 2 hours ago
$68
Roundtrip
found 2 hours ago
ORD
Chicago
DEN
Denver
$143 Roundtrip, found 3 days ago
$143
Roundtrip
found 3 days ago
RFD
Rockford
DEN
Denver
$155 Roundtrip, found 10 hours ago
$155
Roundtrip
found 10 hours ago
ORD
Chicago
EGE
Vail
$211 Roundtrip, found 17 hours ago
$211
Roundtrip
found 17 hours ago
Aspen economy flight packages
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Spark by Hilton Denver International Airport
8.4/10 Very Good! (388 reviews)
Dec 17 - Dec 21
4 night stay
Chicago (CHI) to Denver (DEN)
Southwest Airlines • Coach
Denver (DEN) to Chicago (CHI)
Frontier Airlines • Coach
Save 100% on your flight
Price was $378, price is now $235 per person
$235
per person
found 1 day ago
Nice place, great customer service
Reviewed on Oct 14, 2025
4.0-star property
The Maven Hotel at Dairy Block
9.4/10 Exceptional! (1,151 reviews)
Dec 17 - Dec 21
4 night stay
Chicago (CHI) to Denver (DEN)
Southwest Airlines • Coach
Denver (DEN) to Chicago (CHI)
Frontier Airlines • Coach
Save 100% on your flight
Price was $703, price is now $408 per person
$408
per person
found 1 day ago
Great vibe. Unique.
Reviewed on Oct 27, 2024
4.5-star property
The Source Hotel
8.8/10 Excellent! (1,014 reviews)
Dec 17 - Dec 21
4 night stay
Chicago (CHI) to Denver (DEN)
Southwest Airlines • Coach
Denver (DEN) to Chicago (CHI)
Frontier Airlines • Coach
Save 100% on your flight
Price was $478, price is now $288 per person
$288
per person
found 1 day ago
Great stay! Very friendly and accommodating staff. Attractive aesthetic, wonderful dining, convenient location.
Reviewed on Sep 24, 2025
Aspen packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Renaissance Boulder FlatIron Hotel
8.6/10 Excellent! (1,003 reviews)
Dec 14 - Dec 21
7 night stay
Chicago (ORD) to Denver (DEN)
Delta • Non-stop roundtrip • PremiumEconomy
Price was $944, price is now $682 per person
$682
per person
found 21 hours ago
A 4:00 PM check-in time while pushing a $20 "early" check in time is an egregious money grab, especially when there are fewer than 10 cars in the entire parking lot when we arrived. I will no longer book your hotels if the check in time is not until 4 pm. The lobby bar and restaurant business hours were very haphazard.
Reviewed on May 30, 2025
4.0-star property
The Maven Hotel at Dairy Block
9.4/10 Exceptional! (1,151 reviews)
Dec 14 - Dec 21
7 night stay
Chicago (ORD) to Denver (DEN)
Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,430, price is now $929 per person
$929
per person
found 21 hours ago
Great vibe. Unique.
Reviewed on Oct 27, 2024
4.5-star property
The Source Hotel
8.8/10 Excellent! (1,014 reviews)
Dec 14 - Dec 21
7 night stay
Chicago (ORD) to Denver (DEN)
Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,013, price is now $702 per person
$702
per person
found 21 hours ago
Great stay! Very friendly and accommodating staff. Attractive aesthetic, wonderful dining, convenient location.
Reviewed on Sep 24, 2025
Aspen first class flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Chateau Eau Claire & Roaring Fork by Frias Properties
6.8/10 (5 reviews)
Dec 31 - Jan 4
4 night stay
Chicago (CHI) to Denver (DEN)
American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $3,950, price is now $3,064 per person
$3,064
per person
found 23 hours ago
5.0-star property
Hotel Jerome, Auberge Collection
9.6/10 Exceptional! (442 reviews)
Dec 31 - Jan 4
4 night stay
Chicago (CHI) to Denver (DEN)
American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $8,187, price is now $6,183 per person
$6,183
per person
found 23 hours ago
Beautiful hotel. Very helpful staff. Great location.
Reviewed on May 28, 2019
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
Low Cost Flights From Chicago to Aspen
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Flights to Aspen
- Los Angeles to Aspen
- New York to Aspen
- Chicago to Aspen
- Houston to Aspen
- San Francisco to Aspen
- Newark to Aspen
- San Diego to Aspen
- New Orleans to Aspen
- Austin to Aspen
- Oakland to Aspen
- Rome to Aspen
- Amarillo to Aspen
- Columbia to Aspen
- Great Falls to Aspen
- Honolulu to Aspen
- Karachi to Aspen
- Medellin to Aspen
- Monterrey to Aspen
- Kahului to Aspen
- Placencia to Aspen
Flights from Chicago
- Chicago to Orlando
- Chicago to Houston
- Chicago to New York
- Chicago to Phoenix
- Chicago to Dallas
- Chicago to Los Angeles
- Chicago to London
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- Chicago to Washington
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- Chicago to Toronto
- Chicago to San Francisco
- Chicago to Cleveland
- Chicago to Detroit
- Chicago to Montreal
- Chicago to Sacramento
- Chicago to Kansas City
- Chicago to Hartford
- Chicago to Atlantic City
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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.