Title: CA $304 Cheap Flights from Chicago (MDW) to Aspen (ASE) - Expedia.ca

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# CA $304 Cheap Flights from Chicago (MDW) to Aspen (ASE)

[View CA $304 flight on Tue, Jan 27, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:MDW,to:ASE,departure:27/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:303.30&airProductToken=AQpvCjYIxJgBEgQxMjg1GOywASDgXCjwxoMDMO3HgwM4RUAAWAFqCU1BSU5CQVNJQ3IIVEFWTkEwQlEKNQjEmAESBDQwMTEY4FwgwCQokMiDAzCDyoMDOEVAAVgBaglNQUlOQkFTSUNyCFRBVk5BMEJREgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) 

- [Roundtrip](?flightType=roundtrip)
- [One-way](?flightType=oneway)
- [Multi-city](?flightType=multicity)

### Travellers

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

- ![Delta](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg)  
Delta  
[](https://www.expedia.ca/Flights-Search?leg1=from:MDW,to:ASE,departure:01/01/2026TANYT&leg2=from:ASE,to:MDW,departure:08/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}])

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## Cheap flights from Chicago (MDW) to Aspen (ASE)

Prices were available within the past 7 days and start at CA $304 for one-way flights and CA $831 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

All deals

One way

Roundtrip

![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif)

Wed, Dec 24 - Thu, Dec 25

MDW

Chicago

ASE

Aspen

CA $831

Roundtrip

found 5 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MDW,to:ASE,departure:24/12/2025TANYT&leg2=from:ASE,to:MDW,departure:25/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:830.30&airProductToken=AQpvCjYIxJgBEgQxMjg1GOywASDgXCiwyIADMKjJgAM4TEAAWAFqCU1BSU5DTEFTQ3IITEYwTkEwTVEKNQjEmAESBDM5MTkY4FwgwCQo68qAAzDbzIADOExAAVgBaglNQUlOQ0xBU0NyCExGME5BME1RCm8KNQjEmAESBDM2NzYYwCQg4Fwoo9iAAzD12YADOFRAAFgBaglNQUlOQ0xBU0NyCFRSVU5HOE1MCjYIxJgBEgQxMDc2GOBcIOywASix2oADMKbbgAM4VEABWAFqCU1BSU5DTEFTQ3IIVFJVTkc4TUwSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB)

![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif)

Wed, Dec 24 - Thu, Dec 25

MDW

Chicago

ASE

Aspen

CA $982

Roundtrip

found 5 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MDW,to:ASE,departure:24/12/2025TANYT&leg2=from:ASE,to:MDW,departure:25/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:981.90&airProductToken=AQpvCjYIxJgBEgQxMjg1GOywASDgXCiwyIADMKjJgAM4TEAAWAFqCU1BSU5FWFRSQXIITEYwUkEwTUwKNQjEmAESBDM5MTkY4FwgwCQo68qAAzDbzIADOExAAVgBaglNQUlORVhUUkFyCExGMFJBME1MCm8KNQjEmAESBDM2NzYYwCQg4Fwoo9iAAzD12YADOFRAAFgBaglNQUlORVhUUkFyCFRSVVJHOE1MCjYIxJgBEgQxMDc2GOBcIOywASix2oADMKbbgAM4VEABWAFqCU1BSU5FWFRSQXIIVFJVUkc4TUwSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB)

![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif)

Wed, Dec 24 - Thu, Dec 25

MDW

Chicago

ASE

Aspen

CA $1,059

Roundtrip

found 5 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MDW,to:ASE,departure:24/12/2025TANYT&leg2=from:ASE,to:MDW,departure:25/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1058.20&airProductToken=AQpvCjYIxJgBEgQxMjg1GOywASDgXCiwyIADMKjJgAM4UUAAWAFqCU1BSU5DTEFTQ3IIUUYwT0EwTVEKNQjEmAESBDQwMTEY4FwgwCQo0MmAAzC_y4ADOFFAAVgBaglNQUlOQ0xBU0NyCFFGME9BME1RCm8KNQjEmAESBDM2NzYYwCQg4Fwoo9iAAzD12YADOFRAAFgBaglNQUlOQ0xBU0NyCFRSVU5HOE1MCjYIxJgBEgQxMDc2GOBcIOywASix2oADMKbbgAM4VEABWAFqCU1BSU5DTEFTQ3IIVFJVTkc4TUwSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB)

![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif)

Wed, Dec 24 - Thu, Dec 25

MDW

Chicago

ASE

Aspen

CA $1,253

Roundtrip

found 5 days ago

[](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MDW,to:ASE,departure:24/12/2025TANYT&leg2=from:ASE,to:MDW,departure:25/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1252.80&airProductToken=AQpvCjYIxJgBEgQxMjg1GOywASDgXCiwyIADMKjJgAM4UUAAWAFqCU1BSU5FWFRSQXIIUUYwWkEwTUwKNQjEmAESBDQwMTEY4FwgwCQo0MmAAzC_y4ADOFFAAVgBaglNQUlORVhUUkFyCFFGMFpBME1MCm8KNQjEmAESBDM2NzYYwCQg4Fwoo9iAAzD12YADOFRAAFgBaglNQUlORVhUUkFyCFRSVVJHOE1MCjYIxJgBEgQxMDc2GOBcIOywASix2oADMKbbgAM4VEABWAFqCU1BSU5FWFRSQXIIVFJVUkc4TUwSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB)

## Frequently asked questions

### How much is a flight from MDW to Aspen/Pitkin County Airport?

### Do I need to pay a cancellation fee if I cancel my flight from Midway Intl. Airport (MDW) to Pitkin County Airport (ASE)?

### How do I find cheap flights from Midway Intl. Airport (MDW) to Pitkin County Airport (ASE) that have flexible change policies?

### How many hours is the flight from Midway Airport to ASE?

### How far is the flight from Midway Intl. Airport (MDW) to Aspen/Pitkin County Airport?

### Which airlines fly direct from MDW to Pitkin County Airport (ASE)?

### Are Chicago Airport to Aspen/Pitkin County Airport flight tickets cheaper when they're purchased at the last minute?

## Travel information

| Origin airport      | Midway Intl.  |
| ------------------- | ------------- |
| Destination airport | Pitkin County |
| Roundtrip price     | CA $830       |
| Distance            | 1628 km       |

## Book with confidence

# Chicago to Aspen Flights

**The easy way to book your flights from Chicago to Aspen** 

With Expedia, it’s simple to find and book flights to Aspen from Chicago whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 11 airlines that cover this route. There are nonstop flights to Pitkin County, too. 

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Chicago to Aspen today, tomorrow, or this week. 

**Save dollars with cheap flights from Midway Intl., MDW to Pitkin County, ASE** 

Sort your search results by price to find great deals on your flight from Chicago to Aspen—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Aspen from Chicago currently is just CA $831 rising to CA $1,253\. 

Here are more money-saving tips: 

- Fly in December when flight prices are normally at their lowest
- Book about a month to 6 weeks before you travel for the best prices to Aspen
- Avoid peak season and weekends when flights can cost more
- Early morning and late-night flights are sometimes cheaper, so try varying your travel times
- One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free!

**Reasons to choose Expedia for your flight to Aspen from Chicago** 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Aspen with Expedia today.

\*Available to Expedia members.