$198 Cheap Flights from Aspen (ASE) to Chicago (MDW)

View $198 flight on Wed, Nov 5, 2025Opens in a new window

Popular airlines from Aspen/Pitkin County Airport (ASE) to Chicago Midway Airport (MDW)

Cheap Flights from Aspen to Chicago (ASE-MDW)

Prices were available within the past 7 days and start at $198 for one-way flights and $309 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, Jan 15 - Tue, Jan 27
ASE
Aspen
MDW
Chicago
$309 Roundtrip, found 1 day ago
$309
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Jan 15 from Aspen to Chicago, returning Tue, Jan 27, priced at $309 found 1 day ago
Delta
Thu, Jan 15 - Sun, Feb 1
ASE
Aspen
MDW
Chicago
$334 Roundtrip, found 1 day ago
$334
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Jan 15 from Aspen to Chicago, returning Sun, Feb 1, priced at $334 found 1 day ago
Delta
Wed, Jan 14 - Sun, Jan 18
ASE
Aspen
MDW
Chicago
$339 Roundtrip, found 5 days ago
$339
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Jan 14 from Aspen to Chicago, returning Sun, Jan 18, priced at $339 found 5 days ago
Delta
Wed, Jan 14 - Sun, Feb 1
ASE
Aspen
MDW
Chicago
$359 Roundtrip, found 1 day ago
$359
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jan 14 from Aspen to Chicago, returning Sun, Feb 1, priced at $359 found 1 day ago
Delta
Fri, Jan 23 - Mon, Jan 26
ASE
Aspen
MDW
Chicago
$400 Roundtrip, found 5 days ago
$400
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Jan 23 from Aspen to Chicago, returning Mon, Jan 26, priced at $400 found 5 days ago
Delta
Sat, Jan 24 - Tue, Jan 27
ASE
Aspen
MDW
Chicago
$404 Roundtrip, found 2 days ago
$404
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Jan 24 from Aspen to Chicago, returning Tue, Jan 27, priced at $404 found 2 days ago
Delta
Sat, May 30 - Wed, Jun 3
ASE
Aspen
MDW
Chicago
$419 Roundtrip, found 7 hours ago
$419
Roundtrip
found 7 hours ago
Select Delta flight, departing Sat, May 30 from Aspen to Chicago, returning Wed, Jun 3, priced at $419 found 7 hours ago
Delta
Fri, Dec 5 - Mon, Dec 8
ASE
Aspen
MDW
Chicago
$469 Roundtrip, found 1 hour ago
$469
Roundtrip
found 1 hour ago
Select Delta flight, departing Fri, Dec 5 from Aspen to Chicago, returning Mon, Dec 8, priced at $469 found 1 hour ago
Delta
Wed, Jan 14 - Sun, Jan 18
ASE
Aspen
MDW
Chicago
$479 Roundtrip, found 5 days ago
$479
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Jan 14 from Aspen to Chicago, returning Sun, Jan 18, priced at $479 found 5 days ago
Delta
Fri, Jan 23 - Mon, Jan 26
ASE
Aspen
MDW
Chicago
$480 Roundtrip, found 5 days ago
$480
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Jan 23 from Aspen to Chicago, returning Mon, Jan 26, priced at $480 found 5 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $585
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $585

Frequently asked questions

How much does a flight from Pitkin County Airport (ASE) to Midway Intl. Airport (MDW) cost?
Grab a cheap one-way flight from $198 or cheap return flight from $309 from Pitkin County Airport (ASE) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Pitkin County Airport (ASE) to Midway Intl. Airport (MDW)?
The cheapest month to fly from ASE to MDW is January, when demand is low. Off-peak season is often when airlines offer lower prices between these airports.
What is the cheapest airline that flies from Pitkin County Airport (ASE) to Midway Intl. Airport (MDW)?
Use the filter tool on Expedia to compare different airlines and find the cheapest carrier that'll take you from ASE to MDW. Then, sort your results by "Price (lowest to highest)" to snag a good deal.
How many flights per day from Pitkin County Airport (ASE) to Midway Intl. Airport (MDW)?
Direct flights from Pitkin County Airport (ASE) to Midway Intl. Airport (MDW) aren't available daily, so you'll have to take a flight with a layover. Explore your options with our filter tool. Enter your travel details and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ASE to MDW?
Friday is usually the busiest day for flights, while Tuesday tends to be the quietest.* Keep in mind that flight schedules can change depending on a number of factors, such as the time of year and carrier.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Pitkin County Airport (ASE) to Midway Intl. Airport (MDW)?
To avoid potential delays on the Pitkin County Airport (ASE) to Midway Intl. Airport (MDW) route, travel before 3 PM. Departures after this time are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Pitkin County Airport (ASE)?
If you're flying on a direct flight from Pitkin County Airport (ASE) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can land at.
Is it cheaper to buy a plane ticket from Pitkin County Airport (ASE) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from ASE to MDW are generally more expensive. For the best prices, start looking for flights early. That being said, if you're flexible with your travel plans, you may find a cheap ticket right before your journey.
Is it cheaper to book an ASE to MDW flight and hotel package?
You'll typically save money by booking an ASE to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. Once you've chosen your preferred accommodations and flights, you can add extras such as car rentals, activities and tours.
Can I cancel or change the date of my flight from Pitkin County Airport (ASE) to Midway Intl. Airport (MDW)?
If you booked your ASE to MDW flight within the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the type of fare you have, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for more information.

Travel information

Origin airport
Pitkin County
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$308
Distance
1017 mi

Book with confidence

Aspen to Chicago Flights

The cheapest times to fly from Aspen to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Aspen to Chicago are during the month of January. You can find some of the cheapest flights from Aspen to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Aspen to Chicago

Sunday is one of the best days to book for cheap flights from Aspen to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Aspen to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Aspen to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $198 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Aspen to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Aspen to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Aspen to Chicago Flights

Explore a world of travel with Expedia

*Available to One Key members.