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Cheap flight deals from Chicago to Key West Starting at MYR 467

We've found these cheap flights for you. You can book one-way or round-trip flight tickets.

  • One way
  • Round-trip
      • Cheapest nonstop
        ORD04:42 pm
        3h 21m
        Nonstop
        EYW09:03 pm
        Tue, Mar 18|Chicago - Key West|United Airlines
        MYR 581MYR 785
        26% OFF
        26% OFF
        MYR 785MYR 581

        Choose United Airlines flights from Chicago to Key West. The one-way direct flight with United Airlines departs from O'Hare International Airport on Tue, Mar 18, arriving at Key West International Airport. One-way Prices start from MYR 581 including taxes and charges.

      • MDW12:44 pm
        6h 27m
        1 stop
        EYW08:11 pm
        Tue, Feb 25|Chicago - Key West|Delta Air Lines
        MYR 467MYR 785
        41% OFF
        41% OFF
        MYR 785MYR 467

        Choose Delta Air Lines flights from Chicago to Key West. The one-way connecting flight with Delta Air Lines departs from Midway International Airport on Tue, Feb 25, arriving at Key West International Airport. One-way Prices start from MYR 467 including taxes and charges.

      • MDW09:54 am
        6h 26m
        1 stop
        EYW05:20 pm
        Tue, Mar 18|Chicago - Key West|Delta Air Lines
        MYR 468MYR 785
        40% OFF
        40% OFF
        MYR 785MYR 468

        Choose Delta Air Lines flights from Chicago to Key West. The one-way connecting flight with Delta Air Lines departs from Midway International Airport on Tue, Mar 18, arriving at Key West International Airport. One-way Prices start from MYR 468 including taxes and charges.

      • MDW12:51 pm
        6h 39m
        1 stop
        EYW08:30 pm
        Tue, Mar 25|Chicago - Key West|Delta Air Lines
        MYR 468
        MYR 468

        Choose Delta Air Lines flights from Chicago to Key West. The one-way connecting flight with Delta Air Lines departs from Midway International Airport on Tue, Mar 25, arriving at Key West International Airport. One-way Prices start from MYR 468 including taxes and charges.

      • MDW12:51 pm
        6h 39m
        1 stop
        EYW08:30 pm
        Tue, Apr 1|Chicago - Key West|Delta Air Lines
        MYR 469
        MYR 469

        Choose Delta Air Lines flights from Chicago to Key West. The one-way connecting flight with Delta Air Lines departs from Midway International Airport on Tue, Apr 1, arriving at Key West International Airport. One-way Prices start from MYR 469 including taxes and charges.

      • ORD06:20 am
        9h 55m
        1 stop
        EYW05:15 pm
        Tue, Mar 4|Chicago - Key West|Frontier Airlines
        MYR 505
        MYR 505

        Choose Frontier Airlines flights from Chicago to Key West. The one-way connecting flight with Frontier Airlines departs from O'Hare International Airport on Tue, Mar 4, arriving at Key West International Airport. One-way Prices start from MYR 505 including taxes and charges.

      • ORD06:20 am
        9h 55m
        1 stop
        EYW05:15 pm
        Tue, Feb 25|Chicago - Key West|Frontier Airlines
        MYR 530
        MYR 530

        Choose Frontier Airlines flights from Chicago to Key West. The one-way connecting flight with Frontier Airlines departs from O'Hare International Airport on Tue, Feb 25, arriving at Key West International Airport. One-way Prices start from MYR 530 including taxes and charges.

      • ORD09:32 am
        6h 43m
        1 stop
        EYW05:15 pm
        Tue, Apr 15|Chicago - Key West|Frontier Airlines
        MYR 533
        MYR 533

        Choose Frontier Airlines flights from Chicago to Key West. The one-way connecting flight with Frontier Airlines departs from O'Hare International Airport on Tue, Apr 15, arriving at Key West International Airport. One-way Prices start from MYR 533 including taxes and charges.

      • ORD05:05 am
        11h 10m
        1 stop
        EYW05:15 pm
        Sun, Feb 23|Chicago - Key West|Frontier Airlines
        MYR 540
        MYR 540

        Choose Frontier Airlines flights from Chicago to Key West. The one-way connecting flight with Frontier Airlines departs from O'Hare International Airport on Sun, Feb 23, arriving at Key West International Airport. One-way Prices start from MYR 540 including taxes and charges.

      • ORD07:25 am
        8h 50m
        1 stop
        EYW05:15 pm
        Wed, Mar 5|Chicago - Key West|Frontier Airlines
        MYR 556
        MYR 556

        Choose Frontier Airlines flights from Chicago to Key West. The one-way connecting flight with Frontier Airlines departs from O'Hare International Airport on Wed, Mar 5, arriving at Key West International Airport. One-way Prices start from MYR 556 including taxes and charges.

      • CHI01:00 pm
        3h 5m
        Nonstop
        EYW02:00 pm
        Fri, Feb 28|Chicago - Key West|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.

Chicago to Key West Flight Time

Flight info.
Departure
Arrival
Weekly Schedule

  1. DL2417

    Delta Air Lines

    01:05 pm

    MDW

    2.0h

    04:04 pm

    ATL

    SMTWT-S
    Search

  2. DL2815

    Delta Air Lines

    05:50 pm

    ATL

    1.9h

    07:44 pm

    EYW

    SMTWTFS

  3. DL1477

    Delta Air Lines

    03:35 pm

    ORD

    2.0h

    06:37 pm

    ATL

    SMTWTFS
    Search

  4. DL2815

    Delta Air Lines

    05:50 pm

    ATL

    1.9h

    07:44 pm

    EYW

    SMTWTFS

  5. F91186

    Frontier Airlines

    04:11 pm

    MDW

    2.7h

    07:54 pm

    TPA

    SMTWTFS
    Search

  6. UA3136

    United Airlines

    03:05 pm

    TPA

    1.3h

    04:20 pm

    EYW

    SMTWTFS

  7. DL1264

    Delta Air Lines

    05:50 am

    ORD

    2.0h

    08:52 am

    ATL

    SMTWTFS
    Search

  8. DL1281

    Delta Air Lines

    09:55 am

    ATL

    1.9h

    11:49 am

    EYW

    SMTWTFS

  9. AA2920

    American Airlines

    06:55 am

    ORD

    2.6h

    10:33 am

    TPA

    SMTWTFS
    Search

  10. UA3137

    United Airlines

    04:00 pm

    TPA

    1.3h

    05:15 pm

    EYW

    SMTWTFS

  11. DL1247

    Delta Air Lines

    07:10 am

    ORD

    2.0h

    10:13 am

    ATL

    SMTWTFS
    Search

  12. DL1472

    Delta Air Lines

    11:15 am

    ATL

    1.9h

    01:09 pm

    EYW

    SMTWTFS

  13. F91416

    Frontier Airlines

    09:01 am

    ORD

    2.7h

    12:41 pm

    TPA

    SMTWTFS
    Search

  14. UA3136

    United Airlines

    03:05 pm

    TPA

    1.3h

    04:20 pm

    EYW

    SMTWTFS

  15. DL1063

    Delta Air Lines

    10:10 am

    MDW

    1.9h

    01:05 pm

    ATL

    SMTWTFS
    Search

  16. DL2168

    Delta Air Lines

    03:18 pm

    ATL

    1.9h

    05:13 pm

    EYW

    SMTWTFS

  17. UA1775

    United Airlines

    10:35 am

    ORD

    3.3h

    02:53 pm

    FLL

    SMTWTFS
    Search

  18. UA3094

    United Airlines

    05:50 pm

    FLL

    1.1h

    06:55 pm

    EYW

    SMTWTFS

  19. UA2070

    United Airlines

    10:59 am

    ORD

    3.1h

    Nonstop

    03:04 pm

    EYW

    SMTWTFS
    Search
Find more flights and airlines

When is the cheapest time to fly from Chicago to Key West?

We monitor flight fares to help you find the best deals effortlessly

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

Frequently Asked Questions

  • When are flight tickets from Chicago (CHI) to Key West (EYW) the cheapest?

    Airlines adjust prices for flights from Chicago to Key West based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Chicago (CHI) to Key West (EYW) cost?

    According to Trip.com's data, the lowest price is around MYR 1,943.

  • How long does it take to fly from Chicago (CHI) to Key West (EYW) and what is the distance?

    It takes around 3 hours 8 minutes to fly from Chicago (CHI) to Key West (EYW).

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

    • The distance from Key West International Airport to downtown is about 2 km. It takes about 20 minutes by taxi.

  • What are the most popular airlines that fly from Chicago (CHI) to Key West (EYW)?

    Airlines with flights from Chicago (CHI) to Key West (EYW): Air New Zealand, American Airlines and United Airlines.

How to find a cheap flight from Chicago to Key West

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to Key West. Book your flights at the right time and save more.
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

Flight Info | Chicago to Key West

Cheapest round-trip ticket priceMYR 1,108
Off-season for travelJanuary
Peak season for travelMay
Flight distance2,001.04 km
Average flight time3 hours 8 minutes

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