Users have found that booking a flight from Chicago Midway Airport to Aspen at least 25 days early can save you up to 28% on average compared to booking a flight this week. If booking 25 days before your flight isn’t an option for you, users have found flights from Chicago Midway Airport to Aspen for as little as $359 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $655 for flights departing within the next 3 days.
May can be a great time to fly to Aspen from Chicago Midway Airport with a flight ticket averaging about $558. Cheapflights users have found deals in the month of May for as cheap as $421. The most expensive prices can be found in the month of November.
When flying from Chicago Midway Airport to Aspen, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$699 - $1,669
Route
Depart
Return
Price
Chicago MidwayAspen Pitkin County
MDW - ASE
MDWASE
Chicago Midway
Tue 11/5
1 stop6h 15m
Aspen Pitkin County
Sun 11/10
1 stop8h 31m
Chicago MidwayAspen Pitkin County
MDW - ASE
MDWASE
Chicago Midway
Mon 9/9
1 stop6h 55m
Aspen Pitkin County
Wed 9/11
1 stop6h 13m
Chicago MidwayAspen Pitkin County
MDW - ASE
MDWASE
Chicago Midway
Mon 9/9
1 stop6h 55m
Aspen Pitkin County
Wed 9/11
2 stops8h 19m
Chicago MidwayAspen Pitkin County
MDW - ASE
MDWASE
Chicago Midway
Tue 11/5
1 stop6h 15m
Aspen Pitkin County
Sun 11/10
2 stops9h 20m
Chicago MidwayAspen Pitkin County
MDW - ASE
MDWASE
Chicago Midway
Fri 8/2
1 stop6h 53m
Aspen Pitkin County
Mon 8/5
1 stop6h 07m
Chicago MidwayAspen Pitkin County
MDW - ASE
MDWASE
Chicago Midway
Tue 6/25
1 stop6h 54m
Aspen Pitkin County
Sun 6/30
1 stop6h 10m
Chicago MidwayAspen Pitkin County
MDW - ASE
MDWASE
Chicago Midway
Tue 6/25
1 stop6h 54m
Aspen Pitkin County
Sun 6/30
2 stops9h 45m
Chicago MidwayAspen Pitkin County
MDW - ASE
MDWASE
Chicago Midway
Thu 6/20
1 stop6h 54m
Aspen Pitkin County
Fri 6/21
2 stops9h 51m
Chicago MidwayAspen Pitkin County
MDW - ASE
MDWASE
Chicago Midway
Thu 6/20
1 stop6h 54m
Aspen Pitkin County
Fri 6/21
1 stop6h 10m
No data available for this route at this time. Please check back soon.
Overall
Crew
Food
Boarding
Comfort
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Overall
Crew
Food
Boarding
Comfort
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.