The best pricing can be found in the month of December. Prices to Chicago Midway Airport from Aspen average $558. You can even find prices in December for less than $558, as users have found deals to Chicago Midway Airport from as low as $399. The month of April appears to be one of the more expensive times to travel to Chicago Midway Airport from Aspen. Flying in the targeted month can save you up to 44%.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Aspen to Chicago Midway Airport as you normally would.
Fly from
Fly to
Budget
$563 - $988
Route
Depart
Return
Price
Aspen Pitkin CountyChicago Midway
ASE - MDW
ASEMDW
Aspen Pitkin County
Tue 5/28
1 stop6h 56m
Chicago Midway
Sat 6/1
1 stop6h 42m
Aspen Pitkin CountyChicago Midway
ASE - MDW
ASEMDW
Aspen Pitkin County
Wed 6/12
1 stop6h 10m
Chicago Midway
Sun 6/16
1 stop6h 54m
Aspen Pitkin CountyChicago Midway
ASE - MDW
ASEMDW
Aspen Pitkin County
Wed 6/12
2 stops8h 19m
Chicago Midway
Sun 6/16
1 stop6h 54m
Aspen Pitkin CountyChicago Midway
ASE - MDW
ASEMDW
Aspen Pitkin County
Tue 5/28
2 stops9h 13m
Chicago Midway
Sat 6/1
1 stop6h 42m
Aspen Pitkin CountyChicago Midway
ASE - MDW
ASEMDW
Aspen Pitkin County
Tue 5/28
1 stop6h 56m
Chicago Midway
Sat 6/1
1 stop6h 42m
Aspen Pitkin CountyChicago Midway
ASE - MDW
ASEMDW
Aspen Pitkin County
Tue 5/28
2 stops9h 13m
Chicago Midway
Sat 6/1
1 stop6h 42m
Aspen Pitkin CountyChicago Midway
ASE - MDW
ASEMDW
Aspen Pitkin County
Fri 8/30
1 stop9h 14m
Chicago Midway
Mon 9/2
1 stop6h 42m
Aspen Pitkin CountyChicago Midway
ASE - MDW
ASEMDW
Aspen Pitkin County
Fri 8/30
2 stops9h 21m
Chicago Midway
Mon 9/2
1 stop6h 42m
No data available for this route at this time. Please check back soon.
Boarding
Crew
Entertainment
Overall
Food
Comfort
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.
Boarding
Crew
Entertainment
Overall
Food
Comfort
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.
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