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Cheap flights from Aspen to Chicago from $172

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 6/26. 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

Enter your travel dates to find the best prices.
American Airlines Logo
11:22 am - 3:29 pm
ASE
-
ORD
3h 07mnonstop
American Airlines Logo
11:10 am - 1:16 pm
ORD
-
ASE
3h 06mnonstop
$343American Airlines
Fri, Jul 3 - Mon, Jul 6
American Airlines Logo
11:26 am - 3:35 pm
ASE
-
ORD
3h 09mnonstop
American Airlines Logo
7:04 pm - 9:14 pm
ORD
-
ASE
3h 10mnonstop
$344American Airlines
Thu, Jun 18 - Sun, Jun 21
American Airlines Logo
2:21 pm - 11:39 pm
ASE
-
ORD
8h 18m
1 stop
American Airlines Logo
7:49 pm - 9:56 pm
ORD
-
ASE
3h 07mnonstop
$353American Airlines
Fri, Jul 3 - Mon, Jul 6
American Airlines Logo
12:51 pm - 8:29 pm
ASE
-
ORD
6h 38m
1 stop
American Airlines Logo
5:00 am - 10:01 am
ORD
-
ASE
6h 01m
1 stop
$363American Airlines
Fri, Jul 3 - Mon, Jul 6
Delta Logo
8:05 am - 8:24 pm
ASE
-
ORD
11h 19m
2 stops
Delta Logo
5:30 am - 11:21 am
ORD
-
ASE
6h 51m
1 stop
$368Delta
Wed, Sep 2 - Mon, Sep 7
American Airlines Logo
7:36 am - 3:51 pm
ASE
-
ORD
7h 15m
1 stop
American Airlines Logo
11:10 am - 1:16 pm
ORD
-
ASE
3h 06mnonstop
$391American Airlines
Thu, Jul 23 - Mon, Jul 27
United Airlines Logo
1:00 pm - 5:00 pm
ASE
-
ORD
3h 00mnonstop
United Airlines Logo
5:00 am - 10:51 am
ORD
-
ASE
6h 51m
1 stop
$399United Airlines
Wed, Oct 21 - Sun, Oct 25
United Airlines Logo
2:22 pm - 8:40 pm
ASE
-
ORD
5h 18m
1 stop
United Airlines Logo
5:00 am - 8:46 am
ORD
-
ASE
4h 46m
1 stop
$409United Airlines
Thu, Jul 23 - Mon, Jul 27
Delta Logo
7:20 am - 4:15 pm
ASE
-
MDW
7h 55m
1 stop
Delta Logo
6:05 am - 11:23 am
MDW
-
ASE
6h 18m
1 stop
$421Delta
Wed, Aug 26 - Sat, Aug 29
Delta Logo
7:20 am - 4:15 pm
ASE
-
MDW
7h 55m
1 stop
Delta Logo
6:05 am - 11:23 am
MDW
-
ASE
6h 18m
1 stop
$449Delta
Wed, Aug 26 - Sat, Aug 29

United Airlines flights from Aspen to Chicago

Our best United Airlines deals on Aspen to Chicago flight tickets
United Airlines
Oct 21
ASE1:00 pmAspen Pitkin County
3h 00m
ORD5:00 pmChicago O'Hare Intl
Oct 25
ORD5:00 amChicago O'Hare Intl
6h 51m
1 stop
ASE10:51 amAspen Pitkin County
$399
United Airlines
Jul 23
ASE2:22 pmAspen Pitkin County
5h 18m
1 stop
ORD8:40 pmChicago O'Hare Intl
Jul 27
ORD5:00 amChicago O'Hare Intl
4h 46m
1 stop
ASE8:46 amAspen Pitkin County
$409
United Airlines
May 28
ASE9:00 amAspen Pitkin County
3h 04m
ORD1:04 pmChicago O'Hare Intl
Jun 1
ORD8:52 amChicago O'Hare Intl
3h 09m
ASE11:01 amAspen Pitkin County
$419

American Airlines flights from Aspen to Chicago

Our best American Airlines deals on Aspen to Chicago flight tickets
American Airlines
Jul 3
ASE11:22 amAspen Pitkin County
3h 07m
ORD3:29 pmChicago O'Hare Intl
Jul 6
ORD11:10 amChicago O'Hare Intl
3h 06m
ASE1:16 pmAspen Pitkin County
$343
American Airlines
Jun 18
ASE11:26 amAspen Pitkin County
3h 09m
ORD3:35 pmChicago O'Hare Intl
Jun 21
ORD7:04 pmChicago O'Hare Intl
3h 10m
ASE9:14 pmAspen Pitkin County
$344
American Airlines
Jul 3
ASE2:21 pmAspen Pitkin County
8h 18m
1 stop
ORD11:39 pmChicago O'Hare Intl
Jul 6
ORD7:49 pmChicago O'Hare Intl
3h 07m
ASE9:56 pmAspen Pitkin County
$353

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 May 15, 2026.
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

Cheapest round-trip
Quickest round-trip

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Fri 7/3

11:22 am-3:29 pm

Nonstop3h 07m

Chicago O'Hare Intl

Mon 7/6

11:10 am-1:16 pm

Nonstop3h 06m

$343

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Thu 6/18

11:26 am-3:35 pm

Nonstop3h 09m

Chicago O'Hare Intl

Sun 6/21

7:04 pm-9:14 pm

Nonstop3h 10m

$344

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Fri 7/3

2:21 pm-11:39 pm

1 stop8h 18m

Chicago O'Hare Intl

Mon 7/6

7:49 pm-9:56 pm

Nonstop3h 07m

$353

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Fri 7/3

12:51 pm-8:29 pm

1 stop6h 38m

Chicago O'Hare Intl

Mon 7/6

5:00 am-10:01 am

1 stop6h 01m

$363

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Wed 9/2

8:05 am-8:24 pm

2 stops11h 19m

Chicago O'Hare Intl

Mon 9/7

5:30 am-11:21 am

1 stop6h 51m

$368

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Thu 7/23

7:36 am-3:51 pm

1 stop7h 15m

Chicago O'Hare Intl

Mon 7/27

11:10 am-1:16 pm

Nonstop3h 06m

$391

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Wed 10/21

1:00 pm-5:00 pm

Nonstop3h 00m

Chicago O'Hare Intl

Sun 10/25

5:00 am-10:51 am

1 stop6h 51m

$399

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Thu 7/23

2:22 pm-8:40 pm

1 stop5h 18m

Chicago O'Hare Intl

Mon 7/27

5:00 am-8:46 am

1 stop4h 46m

$409

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Wed 8/26

7:20 am-4:15 pm

1 stop7h 55m

Chicago Midway

Sat 8/29

6:05 am-11:23 am

1 stop6h 18m

$421

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Wed 8/26

7:20 am-4:15 pm

1 stop7h 55m

Chicago Midway

Sat 8/29

6:05 am-11:23 am

1 stop6h 18m

$449

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 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 $0. If you’re not able to fly to Chicago in April, then March is your next best option. Flight prices from Aspen to Chicago during March average around $0.

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 $396. 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 $766.

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 at noon. Flights from Aspen to Chicago during this time can be as low as $404. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $475.

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

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

$328

Fastest flight time

3h 04m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Aspen in the past 72 hours is $328. The best round-trip flight deal from Aspen to Chicago found on momondo in the last 72 hours is $408.
The fastest flight from Aspen to Chicago takes 3h 04m
Direct flights go from Aspen to Chicago every day.
There are 3 airports in Chicago. From Aspen there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from Aspen to Chicago

  • 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 04m.

  • 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
7.1
11,662 reviews
Search American Airlines flights
United AirlinesPriceFrom $232Free CancellationRating
7.4
9,717 reviews
Search United Airlines flights

Traveling to a place near Chicago?

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