Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

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 9/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Aspen to Chicago (ASE-CHI)

Cheap round-trip flights

American Airlines Logo
12:14 pm - 4:12 pmASE-ORD
2h 58mnonstop
American Airlines Logo
9:31 am - 11:41 amORD-ASE
3h 10mnonstop
$229American Airlines
Find Deal
Fri, Sep 19 - Mon, Sep 22
United Airlines Logo
3:25 pm - 9:32 pmASE-ORD
5h 07m1 stop
United Airlines Logo
7:35 pm - 9:45 pmORD-ASE
3h 10mnonstop
$239United Airlines
Find Deal
Fri, Sep 19 - Mon, Sep 22
United Airlines Logo
2:40 pm - 8:41 pmASE-ORD
5h 01m1 stop
United Airlines Logo
5:00 am - 9:27 amORD-ASE
5h 27m1 stop
$249United Airlines
Find Deal
Fri, Sep 19 - Mon, Sep 22
United Airlines Logo
12:25 pm - 4:28 pmASE-ORD
3h 03mnonstop
United Airlines Logo
7:35 pm - 9:45 pmORD-ASE
3h 10mnonstop
$259United Airlines
Find Deal
Thu, Sep 11 - Mon, Sep 15
American Airlines Logo
12:14 pm - 4:12 pmASE-ORD
2h 58mnonstop
American Airlines Logo
9:31 am - 11:41 amORD-ASE
3h 10mnonstop
$269American Airlines
Find Deal
Thu, Oct 2 - Sun, Oct 5
American Airlines Logo
4:34 pm - 11:52 pmASE-ORD
6h 18m1 stop
American Airlines Logo
9:31 am - 11:41 amORD-ASE
3h 10mnonstop
$279American Airlines
Find Deal
Thu, Sep 25 - Sun, Sep 28
United Airlines Logo
11:32 am - 7:57 pmASE-ORD
7h 25m1 stop
United Airlines Logo
7:45 pm - 9:55 pmORD-ASE
3h 10mnonstop
$294United Airlines
Find Deal
Tue, Sep 9 - Fri, Oct 10
Delta Logo
7:16 am - 8:20 pmASE-ORD
12h 04m2 stops
Delta Logo
5:30 am - 11:13 amORD-ASE
6h 43m1 stop
$490Delta
Find Deal
Thu, Sep 25 - Sun, Sep 28
Delta Logo
7:21 am - 8:23 pmASE-ORD
12h 02m2 stops
Delta Logo
5:20 am - 11:10 amORD-ASE
6h 50m1 stop
$524Delta
Find Deal
Sat, Oct 11 - Wed, Oct 15
Delta Logo
7:21 am - 6:25 pmASE-MDW
10h 04m2 stops
Delta Logo
6:00 am - 11:10 amMDW-ASE
6h 10m1 stop
$528Delta
Find Deal
Sat, Oct 11 - Tue, Oct 14

United Airlines flights from Aspen to Chicago

Our best United Airlines deals on Aspen to Chicago flight tickets
United Airlines
Sep 19
ASE3:25 pmAspen Pitkin County
5h 07m
1 stop
ORD9:32 pmChicago O'Hare Intl
Sep 22
ORD7:35 pmChicago O'Hare Intl
3h 10m
ASE9:45 pmAspen Pitkin County
$239
Find similar
United Airlines
Sep 19
ASE2:40 pmAspen Pitkin County
5h 01m
1 stop
ORD8:41 pmChicago O'Hare Intl
Sep 22
ORD5:00 amChicago O'Hare Intl
5h 27m
1 stop
ASE9:27 amAspen Pitkin County
$249
Find similar
United Airlines
Sep 11
ASE12:25 pmAspen Pitkin County
3h 03m
ORD4:28 pmChicago O'Hare Intl
Sep 15
ORD7:35 pmChicago O'Hare Intl
3h 10m
ASE9:45 pmAspen Pitkin County
$259
Find similar

Delta flights from Aspen to Chicago

Our best Delta deals on Aspen to Chicago flight tickets
Delta
Sep 4
ASE7:16 amAspen Pitkin County
12h 07m
2 stops
ORD8:23 pmChicago O'Hare Intl
Sep 7
ORD5:45 amChicago O'Hare Intl
6h 36m
1 stop
ASE11:21 amAspen Pitkin County
$374
Find similar
Delta
Sep 4
ASE7:16 amAspen Pitkin County
12h 07m
2 stops
ORD8:23 pmChicago O'Hare Intl
Sep 7
ORD5:45 amChicago O'Hare Intl
6h 36m
1 stop
ASE11:21 amAspen Pitkin County
$464
Find similar
Delta
Sep 25
ASE7:16 amAspen Pitkin County
12h 04m
2 stops
ORD8:20 pmChicago O'Hare Intl
Sep 28
ORD5:30 amChicago O'Hare Intl
6h 43m
1 stop
ASE11:13 amAspen Pitkin County
$490
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 August 27, 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 9/19

12:14 pm-4:12 pm

Nonstop2h 58m

Chicago O'Hare Intl

Mon 9/22

9:31 am-11:41 am

Nonstop3h 10m

$229

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Fri 9/19

3:25 pm-9:32 pm

1 stop5h 07m

Chicago O'Hare Intl

Mon 9/22

7:35 pm-9:45 pm

Nonstop3h 10m

$239

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Fri 9/19

2:40 pm-8:41 pm

1 stop5h 01m

Chicago O'Hare Intl

Mon 9/22

5:00 am-9:27 am

1 stop5h 27m

$249

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Thu 9/11

12:25 pm-4:28 pm

Nonstop3h 03m

Chicago O'Hare Intl

Mon 9/15

7:35 pm-9:45 pm

Nonstop3h 10m

$259

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Thu 10/2

12:14 pm-4:12 pm

Nonstop2h 58m

Chicago O'Hare Intl

Sun 10/5

9:31 am-11:41 am

Nonstop3h 10m

$269

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Thu 9/25

4:34 pm-11:52 pm

1 stop6h 18m

Chicago O'Hare Intl

Sun 9/28

9:31 am-11:41 am

Nonstop3h 10m

$279

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Tue 9/9

11:32 am-7:57 pm

1 stop7h 25m

Chicago O'Hare Intl

Fri 10/10

7:45 pm-9:55 pm

Nonstop3h 10m

$294

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Thu 9/25

7:16 am-8:20 pm

2 stops12h 04m

Chicago O'Hare Intl

Sun 9/28

5:30 am-11:13 am

1 stop6h 43m

$490

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

Sat 10/11

7:21 am-8:23 pm

2 stops12h 02m

Chicago O'Hare Intl

Wed 10/15

5:20 am-11:10 am

1 stop6h 50m

$524

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Sat 10/11

7:21 am-6:25 pm

2 stops10h 04m

Chicago Midway

Tue 10/14

6:00 am-11:10 am

1 stop6h 10m

$528

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $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 $511. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Aspen to Chicago for around $962.

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 afternoon. Flights from Aspen to Chicago during this time can be as low as $543. 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

$368

Fastest flight time

2h 57m

Direct flights

Mon, Tue, Wed, Fri, Sat and Sun

Airports in Chicago

1 airport
The best one-way flight to Chicago from Aspen in the past 72 hours is $368. The best round-trip flight deal from Aspen to Chicago found on momondo in the last 72 hours is $369.
The fastest flight from Aspen to Chicago takes 2h 57m
Direct flights go from Aspen to Chicago on Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
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 2h 58m.

  • 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
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $289Free CancellationRating
7.4
8,945 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 14 United Airlines flights for this route in a normal week, average airfare is usually $469 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 10,000 reviews) operates around 3 flights from Aspen to Chicago in any given week. The average American Airlines airfare for this route is around $439, 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
Lansing
Portage
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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Mon 9/1
Mon 9/8
By creating a price alert you accept our terms of use and privacy policy.

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