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Cheap flights from Aspen to Chicago from $137

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Aspen to Chicago departing on 1/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

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United Airlines Logo
6:00 pm - 11:57 pmASE-ORD
4h 57m1 stop
United Airlines Logo
9:00 am - 11:17 amORD-ASE
3h 17mnonstop
$299United Airlines
Find Deal
Fri, Apr 10 - Sun, Apr 12
Delta Logo
1:05 pm - 9:56 pmASE-ORD
7h 51m1 stop
Delta Logo
5:23 am - 11:21 amORD-ASE
6h 58m1 stop
$309Delta
Find Deal
Thu, Nov 13 - Sun, Nov 16
Delta Logo
7:21 am - 4:41 pmASE-ORD
8h 20m1 stop
Delta Logo
5:20 am - 11:10 amORD-ASE
6h 50m1 stop
$339Delta
Find Deal
Tue, Nov 4 - Sat, Nov 8
United Airlines Logo
3:50 pm - 7:50 pmASE-ORD
3h 00mnonstop
United Airlines Logo
1:10 pm - 3:29 pmORD-ASE
3h 19mnonstop
$369United Airlines
Find Deal
Thu, Mar 26 - Mon, Mar 30
United Airlines Logo
5:26 pm - 10:53 pmASE-ORD
4h 27m1 stop
United Airlines Logo
1:10 pm - 3:29 pmORD-ASE
3h 19mnonstop
$379United Airlines
Find Deal
Thu, Mar 26 - Mon, Mar 30
Delta Logo
1:05 pm - 10:30 pmASE-ORD
8h 25m1 stop
Delta Logo
5:23 am - 11:21 amORD-ASE
6h 58m1 stop
$386Delta
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Tue, Nov 11 - Fri, Nov 14
American Airlines Logo
12:55 pm - 5:10 pmASE-ORD
3h 15mnonstop
American Airlines Logo
9:51 am - 12:25 pmORD-ASE
3h 34mnonstop
$389American Airlines
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Fri, Dec 19 - Mon, Dec 22
American Airlines Logo
2:53 pm - 7:13 pmASE-ORD
3h 20mnonstop
American Airlines Logo
5:00 am - 12:00 pmORD-ASE
8h 00m1 stop
$399American Airlines
Find Deal
Fri, Dec 19 - Mon, Dec 22
Delta Logo
2:55 pm - 10:22 pmASE-MDW
6h 27m1 stop
Delta Logo
6:00 am - 2:15 pmMDW-ASE
9h 15m1 stop
$419Delta
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Sat, Dec 20 - Mon, Dec 22
American Airlines Logo
7:34 am - 5:17 pmASE-ORD
8h 43m1 stop
American Airlines Logo
1:23 pm - 7:30 pmORD-ASE
7h 07m1 stop
$441American Airlines
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Mon, Nov 17 - Thu, Nov 20

Delta flights from Aspen to Chicago

Our best Delta deals on Aspen to Chicago flight tickets
Delta
Nov 13
ASE1:05 pmAspen Pitkin County
7h 51m
1 stop
ORD9:56 pmChicago O'Hare Intl
Nov 16
ORD5:23 amChicago O'Hare Intl
6h 58m
1 stop
ASE11:21 amAspen Pitkin County
$309
Find similar
Delta
Nov 4
ASE7:21 amAspen Pitkin County
8h 20m
1 stop
ORD4:41 pmChicago O'Hare Intl
Nov 8
ORD5:20 amChicago O'Hare Intl
6h 50m
1 stop
ASE11:10 amAspen Pitkin County
$339
Find similar
Delta
Nov 11
ASE1:05 pmAspen Pitkin County
8h 25m
1 stop
ORD10:30 pmChicago O'Hare Intl
Nov 14
ORD5:23 amChicago O'Hare Intl
6h 58m
1 stop
ASE11:21 amAspen Pitkin County
$386
Find similar

American Airlines flights from Aspen to Chicago

Our best American Airlines deals on Aspen to Chicago flight tickets
American Airlines
Dec 19
ASE12:55 pmAspen Pitkin County
3h 15m
ORD5:10 pmChicago O'Hare Intl
Dec 22
ORD9:51 amChicago O'Hare Intl
3h 34m
ASE12:25 pmAspen Pitkin County
$389
Find similar
American Airlines
Dec 19
ASE2:53 pmAspen Pitkin County
3h 20m
ORD7:13 pmChicago O'Hare Intl
Dec 22
ORD5:00 amChicago O'Hare Intl
8h 00m
1 stop
ASE12:00 pmAspen Pitkin County
$399
Find similar
American Airlines
Nov 17
ASE7:34 amAspen Pitkin County
8h 43m
1 stop
ORD5:17 pmChicago O'Hare Intl
Nov 20
ORD1:23 pmChicago O'Hare Intl
7h 07m
1 stop
ASE7:30 pmAspen Pitkin County
$441
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Aspen to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated October 21, 2025.
Use the filters below to find and compare flights from Aspen to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Fri 4/10

6:00 pm-11:57 pm

1 stop4h 57m

Chicago O'Hare Intl

Sun 4/12

9:00 am-11:17 am

Nonstop3h 17m

$299

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Thu 11/13

1:05 pm-9:56 pm

1 stop7h 51m

Chicago O'Hare Intl

Sun 11/16

5:23 am-11:21 am

1 stop6h 58m

$309

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Tue 11/4

7:21 am-4:41 pm

1 stop8h 20m

Chicago O'Hare Intl

Sat 11/8

5:20 am-11:10 am

1 stop6h 50m

$339

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Thu 3/26

3:50 pm-7:50 pm

Nonstop3h 00m

Chicago O'Hare Intl

Mon 3/30

1:10 pm-3:29 pm

Nonstop3h 19m

$369

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Thu 3/26

5:26 pm-10:53 pm

1 stop4h 27m

Chicago O'Hare Intl

Mon 3/30

1:10 pm-3:29 pm

Nonstop3h 19m

$379

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Tue 11/11

1:05 pm-10:30 pm

1 stop8h 25m

Chicago O'Hare Intl

Fri 11/14

5:23 am-11:21 am

1 stop6h 58m

$386

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Fri 12/19

12:55 pm-5:10 pm

Nonstop3h 15m

Chicago O'Hare Intl

Mon 12/22

9:51 am-12:25 pm

Nonstop3h 34m

$389

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Fri 12/19

2:53 pm-7:13 pm

Nonstop3h 20m

Chicago O'Hare Intl

Mon 12/22

5:00 am-12:00 pm

1 stop8h 00m

$399

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Sat 12/20

2:55 pm-10:22 pm

1 stop6h 27m

Chicago Midway

Mon 12/22

6:00 am-2:15 pm

1 stop9h 15m

$419

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Mon 11/17

7:34 am-5:17 pm

1 stop8h 43m

Chicago O'Hare Intl

Thu 11/20

1:23 pm-7:30 pm

1 stop7h 07m

$441

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Aspen to Chicago

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

What is the typical price of a round-trip flight between Aspen and Chicago?

What is the cheapest month to fly to Chicago?

The month of April is, on average, the cheapest month to fly to Chicago from Aspen, with most prices found around $340. If you’re not able to fly to Chicago in April, then August is your next best option. Flight prices from Aspen to Chicago during August average around $340.

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

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $487. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Aspen to Chicago for around $771.

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

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Aspen to Chicago during this time can be as low as $541. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $646.

What is the cheapest Aspen Pitkin County to Chicago flight route?

Fly from Aspen Pitkin County to Chicago O'Hare Intl for the best Aspen Pitkin County - Chicago flight prices

What cabin class options are available on Aspen Pitkin County to Chicago flights?

There are 4 cabin classes available to choose from on Aspen Pitkin County to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Aspen to Chicago flights?

No. A direct flight is the cheapest option for a flight between Aspen to Chicago.

When to book flights from Aspen to Chicago

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

Cheap Aspen to Chicago (ASE to CHI) flight deals and tips

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

Best Price Found

$335

Fastest flight time

2h 59m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Aspen in the past 72 hours is $335. The best round-trip flight deal from Aspen to Chicago found on momondo in the last 72 hours is $358.
The fastest flight from Aspen to Chicago takes 2h 59m
Direct flights go from Aspen to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
Search flight deals

  • How far is Aspen Pitkin County to Chicago by plane?

    The straight-line distance from Aspen Pitkin County to Chicago is 1021.7 mi. In terms of flight time, this usually takes a little over 3h 00m.

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

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

  • How many operators does momondo search for flights from Aspen Pitkin County Airport to Chicago?

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Aspen Pitkin County Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Aspen to Chicago?

  • What is the most popular airline from Aspen to Chicago?

Best airlines flying from Aspen to Chicago

Compare and see reviews for airlines that fly from Aspen to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $172Free CancellationRating
7.2
11,023 reviews
Search American Airlines flights
United AirlinesPriceFrom $289Free CancellationRating
7.4
8,991 reviews
Search United Airlines flights

  • United Airlines Flights From Aspen to Chicago

    United Airlines flight deals from Aspen to Chicago start from $289 round-trip. Over the 11 United Airlines flights for this route in a normal week, average airfare is usually $409 round-trip - but some users have found much cheaper deals with momondo.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

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 Chicago from Aspen.

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

All flight searches from Aspen to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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

Once you have performed a search for Aspen to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes momondo offers price alerts on flights to Chicago from Aspen. 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.

An easier way to manage your Chicago trip

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport