What is the cheapest airline that flies from Chicago Midway to Aspen Pitkin County?

Delta is the most popular carrier operating from Chicago Midway to Aspen Pitkin County

When did momondo last update prices for flights from Chicago Midway Airport to Aspen Pitkin County Airport?

Prices for flights from Chicago Midway Airport to Aspen Pitkin County Airport were last updated today.

How old do you have to be to fly from Chicago Midway Airport to Aspen Pitkin County Airport?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to Aspen Pitkin County Airport.

What documentation or ID do you need to fly to Aspen Pitkin County Airport?

The travel and health documents required for your trip to Aspen Pitkin County Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Aspen Pitkin County Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$182 Cheap Flights from Chicago Midway Airport to Aspen in 2026

Find the cheapest flights from Chicago Midway Airport to Aspen

Round-trip

One-way

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:00 am - 11:21 am

MDW

ASE

6h 21m

1 stop

1:50 pm - 10:10 pm

ASE

MDW

7h 20m

1 stop

$426Delta

Sat, Nov 7 - Tue, Nov 10

6:00 am - 11:21 am

MDW

ASE

6h 21m

1 stop

7:30 am - 6:05 pm

ASE

MDW

9h 35m

2 stops

$431Delta

Sun, Nov 1 - Sat, Nov 7

6:11 am - 11:23 am

MDW

ASE

6h 12m

1 stop

7:20 am - 4:59 pm

ASE

MDW

8h 39m

2 stops

$494Delta

Sat, Aug 29 - Sat, Sep 5

6:05 am - 11:21 am

MDW

ASE

6h 16m

1 stop

7:35 am - 3:25 pm

ASE

MDW

6h 50m

1 stop

$524Delta

Wed, Sep 30 - Sat, Oct 3

6:05 am - 11:21 am

MDW

ASE

6h 16m

1 stop

7:35 am - 6:20 pm

ASE

MDW

9h 45m

2 stops

$529Delta

Wed, Sep 30 - Sat, Oct 3

6:00 am - 11:21 am

MDW

ASE

6h 21m

1 stop

7:30 am - 4:20 pm

ASE

MDW

7h 50m

1 stop

$554Delta

Thu, Oct 22 - Mon, Oct 26

6:00 am - 11:21 am

MDW

ASE

6h 21m

1 stop

7:30 am - 6:05 pm

ASE

MDW

9h 35m

2 stops

$559Delta

Thu, Oct 22 - Mon, Oct 26

6:05 am - 11:23 am

MDW

ASE

6h 18m

1 stop

7:20 am - 6:33 pm

ASE

MDW

10h 13m

2 stops

$674Delta

Thu, Aug 27 - Thu, Sep 3

6:05 am - 11:23 am

MDW

ASE

6h 18m

1 stop

7:20 am - 3:38 pm

ASE

MDW

7h 18m

1 stop

$749Delta

Thu, Aug 27 - Sat, Aug 29

6:05 am - 11:23 am

MDW

ASE

6h 18m

1 stop

7:20 am - 4:15 pm

ASE

MDW

7h 55m

1 stop

$779Delta

Thu, Aug 27 - Thu, Sep 3

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Delta flights from Chicago Midway Airport to Aspen

Our best Delta deals on Chicago Midway Airport to Aspen flight tickets

Delta

Nov 7

MDW6:00 amChicago Midway

6h 21m

1 stop

ASE11:21 amAspen Pitkin County

Nov 10

ASE1:50 pmAspen Pitkin County

7h 20m

1 stop

MDW10:10 pmChicago Midway

$426

Delta

Nov 1

MDW6:00 amChicago Midway

6h 21m

1 stop

ASE11:21 amAspen Pitkin County

Nov 7

ASE7:30 amAspen Pitkin County

9h 35m

2 stops

MDW6:05 pmChicago Midway

$431

Delta

Aug 29

MDW6:11 amChicago Midway

6h 12m

1 stop

ASE11:23 amAspen Pitkin County

Sep 5

ASE7:20 amAspen Pitkin County

8h 39m

2 stops

MDW4:59 pmChicago Midway

$494

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Aspen that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Sat 11/7

6:00 am-11:21 am

1 stop6h 21m

Aspen Pitkin County

Tue 11/10

1:50 pm-10:10 pm

1 stop7h 20m

$426

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Sun 11/1

6:00 am-11:21 am

1 stop6h 21m

Aspen Pitkin County

Sat 11/7

7:30 am-6:05 pm

2 stops9h 35m

$431

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Sat 8/29

6:11 am-11:23 am

1 stop6h 12m

Aspen Pitkin County

Sat 9/5

7:20 am-4:59 pm

2 stops8h 39m

$494

Quickest round-trip

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Wed 9/30

6:05 am-11:21 am

1 stop6h 16m

Aspen Pitkin County

Sat 10/3

7:35 am-3:25 pm

1 stop6h 50m

$524

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Wed 9/30

6:05 am-11:21 am

1 stop6h 16m

Aspen Pitkin County

Sat 10/3

7:35 am-6:20 pm

2 stops9h 45m

$529

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Thu 10/22

6:00 am-11:21 am

1 stop6h 21m

Aspen Pitkin County

Mon 10/26

7:30 am-4:20 pm

1 stop7h 50m

$554

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Thu 10/22

6:00 am-11:21 am

1 stop6h 21m

Aspen Pitkin County

Mon 10/26

7:30 am-6:05 pm

2 stops9h 35m

$559

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Thu 8/27

6:05 am-11:23 am

1 stop6h 18m

Aspen Pitkin County

Thu 9/3

7:20 am-6:33 pm

2 stops10h 13m

$674

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Thu 8/27

6:05 am-11:23 am

1 stop6h 18m

Aspen Pitkin County

Sat 8/29

7:20 am-3:38 pm

1 stop7h 18m

$749

ChicagoAspen

MDW - ASE

MDWASE

Chicago Midway

Thu 8/27

6:05 am-11:23 am

1 stop6h 18m

Aspen Pitkin County

Thu 9/3

7:20 am-4:15 pm

1 stop7h 55m

$779

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago Midway Airport to Aspen

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the cheapest day to depart on your flight to Aspen?

The cheapest day to depart from Chicago Midway Airport to Aspen is on a Tuesday when prices can be found for as low as $356. The most expensive day to fly to Aspen is Wednesday, with ticket prices averaging around $589.

What is the cheapest time of day to depart on your flight to Aspen?

At noon is the cheapest time of day to fly from Chicago Midway Airport to Aspen when you can find flight prices for as low as $371. Flying to Aspen at noon is an ideal time because this is during off-peak travel hours. Try not to purchase tickets in the evening because they tend to be around $547. Of course, these prices can vary depending on the time of year and what airport you fly to.

When to book flights from Chicago Midway Airport to Aspen

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Aspen according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago Midway Airport to Aspen (MDW to ASE) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Aspen

Fastest flight time	6h 16m
Direct flights	None

The fastest flight from Chicago Midway Airport to Aspen takes 6h 16m

There are no direct flights from Chicago Midway Airport to Aspen. There are no popular flight routes from Chicago Midway Airport to Aspen.

Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Aspen

How far is Chicago Midway to Aspen Pitkin County by plane?
There are 1015.2 mi between Chicago Midway and Aspen Pitkin County. Flights usually cover this in 6h 16m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Chicago Midway Airport to Aspen Pitkin County Airport?
Prices for flights from Chicago Midway Airport to Aspen Pitkin County Airport were last updated today.
How old do you have to be to fly from Chicago Midway Airport to Aspen Pitkin County Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to Aspen Pitkin County Airport.
What documentation or ID do you need to fly to Aspen Pitkin County Airport?
The travel and health documents required for your trip to Aspen Pitkin County Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Aspen Pitkin County Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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Snowmass Village

Carbondale

Buena Vista

Snowmass

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Aspen?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Aspen from Chicago.

Can I find flights from Chicago to Aspen with flexible booking policies on momondo?

Flights from Chicago to Aspen with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Aspen?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Aspen from Chicago.

I’m not ready to book a flight from Chicago to Aspen right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Aspen from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.