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Cheap flights from Aspen to Chicago from $211

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 2/27. 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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Find the cheapest flights from Aspen to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
3:46 pm - 7:47 pm
ASE
-
ORD
3h 01mnonstop
American Airlines Logo
7:15 am - 9:37 am
ORD
-
ASE
3h 22mnonstop
$311American Airlines
mié., mar. 11 - lun., mar. 16
American Airlines Logo
3:46 pm - 7:47 pm
ASE
-
ORD
3h 01mnonstop
American Airlines Logo
10:30 pm - 12:28 pm
ORD
-
ASE
14h 58m
2 stops
$313American Airlines
mié., abr. 1 - mar., abr. 7
American Airlines Logo
11:33 am - 8:04 pm
ASE
-
ORD
7h 31m
1 stop
American Airlines Logo
10:18 am - 12:49 pm
ORD
-
ASE
3h 31mnonstop
$321American Airlines
mié., mar. 11 - lun., mar. 16
American Airlines Logo
2:47 pm - 10:24 pm
ASE
-
ORD
6h 37m
1 stop
American Airlines Logo
10:30 pm - 12:28 pm
ORD
-
ASE
14h 58m
2 stops
$328American Airlines
mié., abr. 1 - mar., abr. 7
American Airlines Logo
11:33 am - 9:05 pm
ASE
-
ORD
8h 32m
1 stop
American Airlines Logo
5:00 am - 11:49 am
ORD
-
ASE
7h 49m
1 stop
$331American Airlines
mié., mar. 11 - lun., mar. 16
American Airlines Logo
4:36 pm - 11:36 pm
ASE
-
ORD
6h 00m
1 stop
American Airlines Logo
5:00 am - 11:49 am
ORD
-
ASE
7h 49m
1 stop
$341American Airlines
mié., mar. 11 - lun., mar. 16
American Airlines Logo
1:24 pm - 5:25 pm
ASE
-
ORD
3h 01mnonstop
American Airlines Logo
12:24 pm - 2:52 pm
ORD
-
ASE
3h 28mnonstop
$356American Airlines
jue., mar. 12 - jue., mar. 19
American Airlines Logo
1:24 pm - 5:25 pm
ASE
-
ORD
3h 01mnonstop
American Airlines Logo
7:10 am - 9:32 am
ORD
-
ASE
3h 22mnonstop
$372American Airlines
mar., mar. 3 - vie., mar. 6
Delta Logo
3:00 pm - 10:33 pm
ASE
-
MDW
6h 33m
1 stop
Delta Logo
6:00 am - 2:14 pm
MDW
-
ASE
9h 14m
1 stop
$755Delta
mar., mar. 3 - vie., mar. 6
Delta Logo
1:45 pm - 10:31 pm
ASE
-
MDW
7h 46m
1 stop
Delta Logo
6:00 am - 2:13 pm
MDW
-
ASE
9h 13m
1 stop
$895Delta
mié., abr. 1 - mar., abr. 7

American Airlines flights from Aspen to Chicago

Our best American Airlines deals on Aspen to Chicago flight tickets
American Airlines
Mar 11
ASE3:46 pmAspen Pitkin County
3h 01m
ORD7:47 pmChicago O'Hare Intl
Mar 16
ORD7:15 amChicago O'Hare Intl
3h 22m
ASE9:37 amAspen Pitkin County
$311
American Airlines
Apr 1
ASE3:46 pmAspen Pitkin County
3h 01m
ORD7:47 pmChicago O'Hare Intl
Apr 7
ORD10:30 pmChicago O'Hare Intl
14h 58m
2 stops
ASE12:28 pmAspen Pitkin County
$313
American Airlines
Mar 11
ASE11:33 amAspen Pitkin County
7h 31m
1 stop
ORD8:04 pmChicago O'Hare Intl
Mar 16
ORD10:18 amChicago O'Hare Intl
3h 31m
ASE12:49 pmAspen Pitkin County
$321

United Airlines flights from Aspen to Chicago

Our best United Airlines deals on Aspen to Chicago flight tickets
United Airlines
Mar 31
ASE6:19 pmAspen Pitkin County
5h 11m
1 stop
ORD12:30 amChicago O'Hare Intl
Apr 5
ORD7:00 amChicago O'Hare Intl
5h 09m
1 stop
ASE11:09 amAspen Pitkin County
$331
United Airlines
Mar 30
ASE6:19 pmAspen Pitkin County
5h 10m
1 stop
ORD12:29 amChicago O'Hare Intl
Apr 4
ORD7:45 amChicago O'Hare Intl
3h 19m
ASE10:04 amAspen Pitkin County
$399
United Airlines
Mar 30
ASE5:16 pmAspen Pitkin County
4h 42m
1 stop
ORD10:58 pmChicago O'Hare Intl
Apr 4
ORD12:55 pmChicago O'Hare Intl
5h 35m
1 stop
ASE5:30 pmAspen Pitkin County
$409

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 enero 29, 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

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

mié. 3/11

3:46 pm-7:47 pm

Nonstop3h 01m

Chicago O'Hare Intl

lun. 3/16

7:15 am-9:37 am

Nonstop3h 22m

$311

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

mié. 4/1

3:46 pm-7:47 pm

Nonstop3h 01m

Chicago O'Hare Intl

mar. 4/7

10:30 pm-12:28 pm

2 stops14h 58m

$313

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

mié. 3/11

11:33 am-8:04 pm

1 stop7h 31m

Chicago O'Hare Intl

lun. 3/16

10:18 am-12:49 pm

Nonstop3h 31m

$321

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

mié. 4/1

2:47 pm-10:24 pm

1 stop6h 37m

Chicago O'Hare Intl

mar. 4/7

10:30 pm-12:28 pm

2 stops14h 58m

$328

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

mié. 3/11

11:33 am-9:05 pm

1 stop8h 32m

Chicago O'Hare Intl

lun. 3/16

5:00 am-11:49 am

1 stop7h 49m

$331

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

mié. 3/11

4:36 pm-11:36 pm

1 stop6h 00m

Chicago O'Hare Intl

lun. 3/16

5:00 am-11:49 am

1 stop7h 49m

$341

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

jue. 3/12

1:24 pm-5:25 pm

Nonstop3h 01m

Chicago O'Hare Intl

jue. 3/19

12:24 pm-2:52 pm

Nonstop3h 28m

$356

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

mar. 3/3

1:24 pm-5:25 pm

Nonstop3h 01m

Chicago O'Hare Intl

vie. 3/6

7:10 am-9:32 am

Nonstop3h 22m

$372

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

mar. 3/3

3:00 pm-10:33 pm

1 stop6h 33m

Chicago Midway

vie. 3/6

6:00 am-2:14 pm

1 stop9h 14m

$755

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

mié. 4/1

1:45 pm-10:31 pm

1 stop7h 46m

Chicago Midway

mar. 4/7

6:00 am-2:13 pm

1 stop9h 13m

$895

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 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 $460. 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 $506. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $550.

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

$320

Fastest flight time

2h 59m

Direct flights

Mon, Tue, Wed, Thu, Sat and Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Aspen in the past 72 hours is $320. The best round-trip flight deal from Aspen to Chicago found on momondo in the last 72 hours is $319.
The fastest flight from Aspen to Chicago takes 2h 59m
Direct flights go from Aspen to Chicago on Monday, Tuesday, Wednesday, Thursday, Saturday and Sunday. There are no airlines offering direct flights.
There are 3 airports in Chicago. From Aspen there are direct flights to 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 2h 59m.

  • 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
11,205 reviews
Search American Airlines flights
United AirlinesPriceFrom $319Free CancellationRating
7.4
9,215 reviews
Search United Airlines flights

  • United Airlines Flights From Aspen to Chicago

    United Airlines flight deals from Aspen to Chicago start from $319 round-trip. Over the 19 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.

  • American Airlines Flights From Aspen to Chicago

    American Airlines (7.2/10 from 11,205 reviews) operates around 12 flights from Aspen to Chicago in any given week. The average American Airlines airfare for this route is around $404, with deals from around $172 rare but found on momondo. Referenced prices are for round-trip Aspen to Chicago flight searches in the last 72 hours.

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
Munster
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.

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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