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Cheap Flights from Aspen to Chicago
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Cheap Flights from Aspen to Chicago starting at £ 144

For as little as £ 144, you can take your next adventure to Chicago without breaking the bank. Choose between one-way and return tickets from Aspen below.

  • One way
  • Round-trip
      • Cheapest nonstop
        ASE08:15
        3h 8m
        Nonstop
        ORD12:23
        Tue, Jan 28|Aspen - Chicago|United Airlines
        £ 144£ 298
        52% OFF
        52% OFF
        £ 298£ 144

        Fly from Aspen to Chicago on Tue, Jan 28 with United Airlines. One-way direct flights with United Airlines depart Aspen-Pitkin County Airport and arrive O'Hare International Airport starting at £ 144 including taxes and charges.

      • ASE12:27
        3h
        Nonstop
        ORD16:27
        Tue, Jan 28|Aspen - Chicago|American Airlines
        £ 230£ 298
        23% OFF
        23% OFF
        £ 298£ 230

        Fly from Aspen to Chicago on Tue, Jan 28 with American Airlines. One-way direct flights with American Airlines depart Aspen-Pitkin County Airport and arrive O'Hare International Airport starting at £ 230 including taxes and charges.

      • ASE16:25
        3h
        Nonstop
        ORD20:25
        Sat, Feb 8|Aspen - Chicago|United Airlines
        £ 244£ 298
        18% OFF
        18% OFF
        £ 298£ 244

        Fly from Aspen to Chicago on Sat, Feb 8 with United Airlines. One-way direct flights with United Airlines depart Aspen-Pitkin County Airport and arrive O'Hare International Airport starting at £ 244 including taxes and charges.

      • ASE15:10
        7h 49m
        1 stop
        ORD23:59
        Tue, Jan 28|Aspen - Chicago|Delta Air Lines
        £ 167
        £ 167

        Fly from Aspen to Chicago on Tue, Jan 28 with Delta Air Lines. One-way connecting flights with Delta Air Lines depart Aspen-Pitkin County Airport and arrive O'Hare International Airport starting at £ 167 including taxes and charges.

      • ASE07:00
        6h 11m
        1 stop
        ORD14:11
        Mon, Feb 3|Aspen - Chicago|United Airlines
        £ 231
        £ 231

        Fly from Aspen to Chicago on Mon, Feb 3 with United Airlines. One-way connecting flights with United Airlines depart Aspen-Pitkin County Airport and arrive O'Hare International Airport starting at £ 231 including taxes and charges.

      • ASE13:42
        7h 38m
        1 stop
        MDW22:20
        Fri, Feb 7|Aspen - Chicago|Delta Air Lines
        £ 238
        £ 238

        Fly from Aspen to Chicago on Fri, Feb 7 with Delta Air Lines. One-way connecting flights with Delta Air Lines depart Aspen-Pitkin County Airport and arrive Midway International Airport starting at £ 238 including taxes and charges.

      • ASE15:21
        7h 56m
        1 stop
        MDW00:17
        Wed, Mar 5|Aspen - Chicago|United Airlines
        £ 243
        £ 243

        Fly from Aspen to Chicago on Wed, Mar 5 with United Airlines. One-way connecting flights with United Airlines depart Aspen-Pitkin County Airport and arrive Midway International Airport starting at £ 243 including taxes and charges.

      • ASE10:38
        12h 54m
        1 stop
        ORD00:32
        Sun, Jan 19|Aspen - Chicago|United Airlines
        £ 244
        £ 244

        Fly from Aspen to Chicago on Sun, Jan 19 with United Airlines. One-way connecting flights with United Airlines depart Aspen-Pitkin County Airport and arrive O'Hare International Airport starting at £ 244 including taxes and charges.

      • ASE13:39
        9h 17m
        1 stop
        ORD23:56
        Wed, Mar 26|Aspen - Chicago|Delta Air Lines
        £ 244
        £ 244

        Fly from Aspen to Chicago on Wed, Mar 26 with Delta Air Lines. One-way connecting flights with Delta Air Lines depart Aspen-Pitkin County Airport and arrive O'Hare International Airport starting at £ 244 including taxes and charges.

      • ASE17:02
        6h 15m
        1 stop
        MDW00:17
        Fri, Feb 7|Aspen - Chicago|United Airlines
        £ 247
        £ 247

        Fly from Aspen to Chicago on Fri, Feb 7 with United Airlines. One-way connecting flights with United Airlines depart Aspen-Pitkin County Airport and arrive Midway International Airport starting at £ 247 including taxes and charges.

      • ASE01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Sat, Jan 25|Aspen - Chicago|United Airlines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Cheapest time to fly from Aspen to Chicago

Explore the best time to buy affordable tickets to Chicago with our price trend chart, which predicts how flight prices will change in the coming weeks from previous data.

Displayed prices are calculated based on the lowest average weekly prices of the corresponding route on Trip.com.

Alternative Routes from Aspen to Chicago

Searching for potential routes that might be cheaper and faster? There are a few alternative ways to get to Chicago from Aspen which could help you save money and time.

  • Cheapest
    United Airlines
    ASE
    08:15
    3h 8m
    Nonstop
    ORD
    12:23
    Aspen-Pitkin County Airport - O'Hare International Airport
    Tue, Jan 28United Airlines
    £ 144
  • Delta Air Lines
    ASE
    15:10
    6h 10m
    1 transfer
    MDW
    22:20
    Aspen-Pitkin County Airport - Midway International Airport
    Tue, Jan 28Delta Air Lines
    £ 192
  • Delta Air Lines
    ASE
    15:10
    6h 10m
    1 transfer
    MDW
    22:20
    Aspen-Pitkin County Airport - Midway International Airport
    Tue, Jan 28Delta Air Lines
    £ 192
    Find More Flights

Frequently Asked Questions

  • When to buy flight tickets from Aspen (ASE) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Aspen to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much is a flight from Aspen (ASE) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around £ 355.

  • How long is a flight from Aspen (ASE) to Chicago (CHI)?

    It takes about 2 hours 57 minutes to fly from Aspen (ASE) to Chicago (CHI).

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.

  • What are the most popular airlines that fly from Aspen (ASE) to Chicago (CHI)?

    Airlines with flights from Aspen (ASE) to Chicago (CHI): Qatar Airways, United Airlines, American Airlines and Lufthansa.

  • What's the most popular airline for direct flights from Aspen (ASE) to Chicago (CHI)?

    American Airlines operates 1 direct flights from Aspen (ASE) to Chicago (CHI).

  • How many airports in Chicago?

How to find a cheap flight from Aspen to Chicago

If you leave it until the last minute and forget to check some of the key information when booking tickets, prices can often end up skyrocketing. Below, you can find our top tips for getting the best value flights – from changing dates to chasing deals, there are plenty ways to keep your next trip affordable.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Find cheapest flight ticket from Aspen to Chicago

Cheapest direct flight price£ 143
Cheapest return ticket price£ 319
Off-season for travelJanuary
Peak season for travelOctober
Flight distance1,647.6km
Average flight time2 hours 57 minutes
Popular airlineUnited Airlines

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