Find flights
Deals
Insights
When to book
FAQs & Tips

MDW - ASE

Find cheap flights from Chicago Midway Airport to Aspen from $369

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Aspen departing on 5/3. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Mon 5/27
Mon 6/3

Search hundreds of travel sites at once for deals on flights to Aspen

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Aspen, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Aspen, as well as popular online travel agencies
In the last 7 days travelers have searched 44,335,567 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Midway to Aspen (MDW-ASE)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Aspen that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
6:00 am - 11:54 amMDW-ASE
6h 54m1 stop
7:45 am - 5:04 pmASE-MDW
8h 19m2 stops
$489Delta
Find Deal
Sun, Jun 9 - Fri, Jun 14
6:00 am - 11:54 amMDW-ASE
6h 54m1 stop
7:45 am - 2:55 pmASE-MDW
6h 10m1 stop
$518Delta
Find Deal
Sun, Jun 9 - Fri, Jun 14
6:00 am - 11:42 amMDW-ASE
6h 42m1 stop
7:45 am - 5:59 pmASE-MDW
9h 14m1 stop
$1,088Delta
Find Deal
Thu, Aug 15 - Sun, Aug 18
6:00 am - 11:42 amMDW-ASE
6h 42m1 stop
7:45 am - 2:57 pmASE-MDW
6h 12m1 stop
$1,669Delta
Find Deal
Fri, Aug 16 - Sun, Aug 18
6:00 am - 11:42 amMDW-ASE
6h 42m1 stop
7:45 am - 6:06 pmASE-MDW
9h 21m2 stops
$1,674Delta
Find Deal
Thu, Aug 15 - Sun, Aug 18
6:00 am - 11:42 amMDW-ASE
6h 42m1 stop
7:45 am - 6:06 pmASE-MDW
9h 21m2 stops
$3,677Delta
Find Deal
Fri, Aug 16 - Sun, Aug 18

Flights from Midway to Aspen - Travel Insights & Trends

Get data-powered insights and trends into flights from Midway to Aspen to help you find the cheapest flights, the best time to fly and much more.

How far in advance should I book a flight from Chicago Midway Airport to Aspen?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to Aspen, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to Aspen, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 46 days before departure.

Good to know

Cheapest flight

$369
Flight from Chicago Midway Airport to Aspen

When to book flights from Midway to Aspen

Are your dates flexible? Find out the best times to travel from Midway to Aspen based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Aspen flights

  • What is the cheapest flight from Chicago Midway Airport to Aspen?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Aspen was $369 for a one-way ticket and $489 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Aspen?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from Chicago Midway Airport to Aspen?

    Chicago Midway Airport and Aspen are both served by 1 main airport. You will leave Chicago Midway Airport from Chicago Midway and will be arriving at Aspen Pitkin County.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Aspen?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago Midway Airport to Aspen?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Aspen.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Aspen?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Aspen.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Aspen?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Aspen from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Aspen?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Aspen with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and ASE can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Aspen?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Aspen from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Book cheap flights from Chicago to Aspen

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Aspen found on KAYAK in the last 72 hours.
5/3Fri
1 stopDelta
6h 21mMDW-ASE
$369

Search by stops

Search by airline

Search by price

Chicago Midway Airport - Aspen Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

Aspen (ASE)United States

Return flight deals:

Aspen - Chicago Midway Airport

Cabin classes:

Browse origins:

Browse destinations: