Cheap flights from MDW to ASE (Midway Intl. to Pitkin County)
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Cheap Flights from MDW to ASE starting at $612 One Way, $780 Round Trip
Prices starting at $780 for return flights and $612 for one-way flights to Pitkin County 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
ASE
Aspen
$780 Roundtrip, found 2 days ago
$780
Roundtrip
found 2 days ago
MDW
Chicago
ASE
Aspen
$815 Roundtrip, found 2 days ago
$815
Roundtrip
found 2 days ago
MDW
Chicago
ASE
Aspen
$1,025 Roundtrip, found 2 days ago
$1,025
Roundtrip
found 2 days ago
MDW
Chicago
ASE
Aspen
$1,035 Roundtrip, found 2 days ago
$1,035
Roundtrip
found 2 days ago
MDW
Chicago
ASE
Aspen
$1,054 Roundtrip, found 2 days ago
$1,054
Roundtrip
found 2 days ago
Hotel Ideas near Pitkin County
Airport Hotels near Pitkin County
The Inn at Aspen
38750 CO-82 Aspen CO
$224 nightly
The price is $239 total per night from Dec 17 to Dec 18
$239 total
Dec 17 - Dec 18
Total with taxes and fees
Book a stay at this ski hotel in Aspen. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our ...
8.6/10 Excellent! (1,002 reviews)
Nice rooms Right on Buttermilk ski resort Close to airport
Reviewed on Dec 9, 2025
St. Moritz Lodge & Condominiums
334 W Hyman Ave Aspen CO
$185 nightly
The price is $206 total per night from Dec 15 to Dec 16
$206 total
Dec 15 - Dec 16
Total with taxes and fees
Book a stay at this ski hotel in Aspen. Enjoy free WiFi, free parking, and a free ski shuttle. Our guests praise the breakfast and the pool in our reviews. Popular ...
9/10 Wonderful! (1,004 reviews)
Awesome spot, convenient location and a nice retro sort of charm to the common areas
Reviewed on Dec 8, 2025
The Gant
610 SOUTH WEST END STREET Aspen CO
$671 nightly
The price is $780 total per night from Dec 15 to Dec 16
$780 total
Dec 15 - Dec 16
Total with taxes and fees
Book a stay at this boutique condo in Aspen. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (941 reviews)
Fantastic stay at the Gant, and all the staff are amazing and very accommodating. We can’t wait to be back!
Reviewed on Dec 10, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Hotels In Aspen
The Gant
610 SOUTH WEST END STREET Aspen CO
$671 nightly
The price is $780 total per night from Dec 15 to Dec 16
$780 total
Dec 15 - Dec 16
Total with taxes and fees
Book a stay at this boutique condo in Aspen. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (941 reviews)
Fantastic stay at the Gant, and all the staff are amazing and very accommodating. We can’t wait to be back!
Reviewed on Dec 10, 2025
The Inn at Aspen
38750 CO-82 Aspen CO
$224 nightly
The price is $239 total per night from Dec 17 to Dec 18
$239 total
Dec 17 - Dec 18
Total with taxes and fees
Book a stay at this ski hotel in Aspen. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our ...
8.6/10 Excellent! (1,002 reviews)
Nice rooms Right on Buttermilk ski resort Close to airport
Reviewed on Dec 9, 2025
St. Moritz Lodge & Condominiums
334 W Hyman Ave Aspen CO
$185 nightly
The price is $206 total per night from Dec 15 to Dec 16
$206 total
Dec 15 - Dec 16
Total with taxes and fees
Book a stay at this ski hotel in Aspen. Enjoy free WiFi, free parking, and a free ski shuttle. Our guests praise the breakfast and the pool in our reviews. Popular ...
9/10 Wonderful! (1,004 reviews)
Awesome spot, convenient location and a nice retro sort of charm to the common areas
Reviewed on Dec 8, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Aspen Hotels With Airport Transportation
Hotel Aspen
110 W Main St Aspen CO
Book a stay at this business-friendly hotel in Aspen. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Aspen Mountain and Buttermilk Mountain ...
The rooms were really old and had a run down feeling. The rugs were visibly dirty, the towels were cleaned, but had stains, and there was no clear statement (that I saw) that there is no elevator. The fireplace suites are not worth the extra cost-- the couches are old and discolored, and the fireplace ...
Reviewed on Oct 4, 2022
Alpenblick by Frias Properties
710 S. Mill Street Aspen CO
Stay at this vacation home in Aspen. Enjoy free WiFi, free parking, and a free airport shuttle. Popular attractions Aspen Mountain and Buttermilk Mountain are ...
A terrific location.
The shuttle service to and from the airport was a nice treat as was the location.
Reviewed on Jul 18, 2017
Alpenblick Townhomes
710 South Mill St Aspen CO
Book a stay at this ski apartment in Aspen. Enjoy free WiFi, free parking, and a golf course. Popular attractions Aspen Mountain and Buttermilk Mountain are ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Low Priced Aspen Hotels
St. Moritz Lodge & Condominiums
334 W Hyman Ave Aspen CO
$185 nightly
The price is $206 total per night from Dec 15 to Dec 16
$206 total
Dec 15 - Dec 16
Total with taxes and fees
Book a stay at this ski hotel in Aspen. Enjoy free WiFi, free parking, and a free ski shuttle. Our guests praise the breakfast and the pool in our reviews. Popular ...
9/10 Wonderful! (1,004 reviews)
Awesome spot, convenient location and a nice retro sort of charm to the common areas
Reviewed on Dec 8, 2025
Tyrolean Lodge
200 West Main St Aspen CO
$211 nightly
The price is $235 total per night from Dec 15 to Dec 16
$235 total
Dec 15 - Dec 16
Total with taxes and fees
Book a stay at this ski hotel in Aspen. Enjoy free WiFi, free parking, and 20 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (660 reviews)
Yes
Reviewed on Dec 3, 2025
Hotel Aspen
110 W Main St Aspen CO
Book a stay at this business-friendly hotel in Aspen. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Aspen Mountain and Buttermilk Mountain ...
The rooms were really old and had a run down feeling. The rugs were visibly dirty, the towels were cleaned, but had stains, and there was no clear statement (that I saw) that there is no elevator. The fireplace suites are not worth the extra cost-- the couches are old and discolored, and the fireplace ...
Reviewed on Oct 4, 2022
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Family Friendly Hotels in Aspen
Mountain Chalet Aspen
333 East Durant Avenue Aspen CO
Stay at this hotel in Aspen. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.6/10 Excellent! (1,001 reviews)
Older property, but great location. Parking was very difficult. Very central to everything downtown
Reviewed on Jun 4, 2024
Hotel Durant
122 East Durant Aspen CO
$315 nightly
The price is $351 total per night from Dec 15 to Dec 16
$351 total
Dec 15 - Dec 16
Total with taxes and fees
Book a stay at this ski hotel in Aspen. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Aspen Mountain and Buttermilk Mountain are located ...
8.8/10 Excellent! (743 reviews)
Staff was friendly, rooms were small but cute and clean
Reviewed on Oct 19, 2025
Limelight Hotel Aspen
355 S. Monarch St Aspen CO
$703 nightly
The price is $782 total per night from Dec 15 to Dec 16
$782 total
Dec 15 - Dec 16
Total with taxes and fees
Book a stay at this boutique hotel in Aspen. Enjoy free breakfast, 2 hot tubs, and a free airport shuttle. Our guests praise the breakfast and the helpful staff ...
9.6/10 Exceptional! (1,000 reviews)
Families like: Outdoor pool, kitchenette, babysitting, skiing nearby
Travelers say...
Everyone and everything was amazing. Staff were nice and friendly, the room was spotless every day and you can’t say enough about how amazing the breakfast is. In a town where a good bang for your buck is hard to come by, the Limelight is a fantastic option regardless of your price point.
Reviewed on Dec 8, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
MDW to ASE Route Info
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MDW Address & GPS
Address:
5700 South Cicero
Chicago IL, 60638
United States
IATA Code:
MDW
Longitude:
-87.740871
Latitude:
41.788136
Time Zone:
America/Chicago
ASE Address & GPS
Address:
233 East Airport Road
Aspen CO, 81611
United States
IATA Code:
ASE
Longitude:
-106.864688
Latitude:
39.219685
Time Zone:
America/Denver
Other Flights from Midway Intl. Airport (MDW)
Other Flights to Pitkin County Airport (ASE)
- O'Hare Intl. Airport (ORD)
- Chicago Executive Airport (PWK)
- Dupage Airport (DPA)
- Kenosha Regional Airport (ENW)
- South Bend Intl. Airport (SBN)
- Greater Rockford Airport (RFD)
- General Mitchell Intl. Airport (MKE)
- Waukesha County Airport (UES)
- Goshen Municipal Airport (GSH)
- Purdue University Airport (LAF)
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Frequently asked questions
Map To Nearby Hotels
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.