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Cheap flight deals from Key West to Chicago Starting at €104

Whether you’re going for a one-way or round-trip to Chicago, we’ve got you covered! Check out these different flight options from Key West below.

  • One way
  • Round-trip
      • Cheapest nonstop
        EYW16:04
        3h 35m
        Nonstop
        ORD18:39
        Thu, Apr 3|Key West - Chicago|United Airlines
        €286€555
        49% OFF
        49% OFF
        €555€286

        Choose United Airlines flights from Key West to Chicago. The one-way direct flight with United Airlines departs from Key West International Airport on Thu, Apr 3, arriving at O'Hare International Airport. One-way Prices start from €286 including taxes and charges.

      • EYW16:07
        3h 42m
        Nonstop
        ORD18:49
        Mon, Feb 24|Key West - Chicago|United Airlines
        €411€555
        26% OFF
        26% OFF
        €555€411

        Choose United Airlines flights from Key West to Chicago. The one-way direct flight with United Airlines departs from Key West International Airport on Mon, Feb 24, arriving at O'Hare International Airport. One-way Prices start from €411 including taxes and charges.

      • EYW18:16
        5h 4m
        1 stop
        MDW22:20
        Wed, Feb 26|Key West - Chicago|Delta Air Lines
        €104€555
        81% OFF
        81% OFF
        €555€104

        Choose Delta Air Lines flights from Key West to Chicago. The one-way connecting flight with Delta Air Lines departs from Key West International Airport on Wed, Feb 26, arriving at Midway International Airport. One-way Prices start from €104 including taxes and charges.

      • EYW14:00
        9h 51m
        1 stop
        MDW22:51
        Sat, Mar 1|Key West - Chicago|United Airlines
        €115
        €115

        Choose United Airlines flights from Key West to Chicago. The one-way connecting flight with United Airlines departs from Key West International Airport on Sat, Mar 1, arriving at Midway International Airport. One-way Prices start from €115 including taxes and charges.

      • EYW10:00
        14h
        1 stop
        MDW23:00
        Wed, Feb 26|Key West - Chicago|United Airlines
        €120
        €120

        Choose United Airlines flights from Key West to Chicago. The one-way connecting flight with United Airlines departs from Key West International Airport on Wed, Feb 26, arriving at Midway International Airport. One-way Prices start from €120 including taxes and charges.

      • EYW10:00
        14h
        1 stop
        MDW23:00
        Wed, Feb 26|Key West - Chicago|Silver Airways
        €121
        €121

        Choose Silver Airways flights from Key West to Chicago. The one-way connecting flight with Silver Airways departs from Key West International Airport on Wed, Feb 26, arriving at Midway International Airport. One-way Prices start from €121 including taxes and charges.

      • EYW19:40
        13h 10m
        1 stop
        ORD07:50
        Sun, Apr 20|Key West - Chicago|United Airlines
        €126
        €126

        Choose United Airlines flights from Key West to Chicago. The one-way connecting flight with United Airlines departs from Key West International Airport on Sun, Apr 20, arriving at O'Hare International Airport. One-way Prices start from €126 including taxes and charges.

      • EYW10:00
        13h 36m
        1 stop
        MDW22:36
        Sat, Apr 19|Key West - Chicago|Silver Airways
        €129
        €129

        Choose Silver Airways flights from Key West to Chicago. The one-way connecting flight with Silver Airways departs from Key West International Airport on Sat, Apr 19, arriving at Midway International Airport. One-way Prices start from €129 including taxes and charges.

      • EYW18:00
        7h 19m
        1 stop
        ORD00:19
        Mon, Apr 21|Key West - Chicago|United Airlines
        €130
        €130

        Choose United Airlines flights from Key West to Chicago. The one-way connecting flight with United Airlines departs from Key West International Airport on Mon, Apr 21, arriving at O'Hare International Airport. One-way Prices start from €130 including taxes and charges.

      • EYW14:00
        10h
        1 stop
        MDW23:00
        Wed, Mar 5|Key West - Chicago|United Airlines
        €134
        €134

        Choose United Airlines flights from Key West to Chicago. The one-way connecting flight with United Airlines departs from Key West International Airport on Wed, Mar 5, arriving at Midway International Airport. One-way Prices start from €134 including taxes and charges.

      • EYW01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Fri, Feb 28|Key West - 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.

Key West to Chicago flight time & flight schedules

Flight info.
Departure
Arrival
Weekly Schedule

  1. UA1513

    United Airlines

    14:18

    EYW

    3.2h

    17:30

    EWR

    SMTWTFS
    Search

  2. UA254

    United Airlines

    18:35

    EWR

    2.8h

    20:25

    ORD

    SMTWTFS

  3. UA3073

    United Airlines

    15:05

    EYW

    1.4h

    16:30

    MCO

    SMTWTFS
    Search

  4. F93043

    Frontier Airlines

    13:40

    MCO

    3.2h

    15:53

    ORD

    SM--TF-

  5. 3M073

    Silver Airways

    15:05

    EYW

    1.4h

    16:30

    MCO

    SMTWTFS
    Search

  6. UA2677

    United Airlines

    19:34

    MCO

    3.2h

    21:44

    ORD

    SMTWTFS

  7. UA3073

    United Airlines

    15:05

    EYW

    1.4h

    16:30

    MCO

    SMTWTFS
    Search

  8. UA2677

    United Airlines

    19:34

    MCO

    3.2h

    21:44

    ORD

    SMTWTFS

  9. AA1222

    American Airlines

    15:07

    EYW

    2.4h

    17:29

    CLT

    SMTWTFS
    Search

  10. AA815

    American Airlines

    20:30

    CLT

    2.2h

    21:44

    ORD

    SMTWTFS

  11. UA3137

    United Airlines

    17:05

    EYW

    1.3h

    18:20

    TPA

    SMTWTFS
    Search

  12. F92317

    Frontier Airlines

    21:42

    TPA

    3.1h

    23:46

    ORD

    -----F-

  13. 3M137

    Silver Airways

    18:00

    EYW

    1.3h

    19:15

    TPA

    SMTWTFS
    Search

  14. F92317

    Frontier Airlines

    21:42

    TPA

    3.1h

    23:46

    ORD

    -----F-

  15. DL2168

    Delta Air Lines

    18:00

    EYW

    2.1h

    20:07

    ATL

    SMTWTFS
    Search

  16. DL1199

    Delta Air Lines

    22:55

    ATL

    2.2h

    00:06

    ORD

    SMTWTFS

  17. 3M137

    Silver Airways

    18:00

    EYW

    1.3h

    19:15

    TPA

    SMTWTFS
    Search

  18. F93899

    Frontier Airlines

    20:59

    TPA

    2.8h

    22:47

    MDW

    S-TWTF-

  19. DL2168

    Delta Air Lines

    18:00

    EYW

    2.1h

    20:07

    ATL

    SMTWTFS
    Search

  20. DL1076

    Delta Air Lines

    20:50

    ATL

    1.9h

    21:46

    MDW

    SMTWTFS
Find more flights and airlines

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

These price trend charts carefully monitor and predict how flight prices from Key West to Chicago will change. Keep a close eye on them to understand when the best time to buy your tickets is.

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 Key West (EYW) to Chicago (CHI) the cheapest?

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

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

    According to Trip.com's data, the lowest price is around €391.

  • How long does it take to fly from Key West (EYW) to Chicago (CHI)?

    It takes about 5 hours 52 minutes to fly from Key West (EYW) 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 25 km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14 km, by taxi about 30 minutes.

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

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

  • What's the most popular airline for non-stop flights from Key West (EYW) to Chicago (CHI)?

    American Airlines operates 4 non-stop flights from Key West (EYW) to Chicago (CHI).

  • How many airports are there in Chicago (CHI)?

How to find a cheap flight from Key West to Chicago

Understanding the common pitfalls when booking your flight tickets can help you save massively when it comes time to fly. We’ve listed our six essential steps to keep in mind when you’re booking flight tickets to help you find the best price.
1
Being flexible with your dates to get the cheapest Key West to Chicago ticket.
Tap "Date" on flight search bar to scan through the calender for Key West to Chicago airfare over next 6 months in 2025. If you would like to fly in next 3 months, it seems the cheapest date is on Thu, Apr 3 at €286 for one-way flights.
2
Compare cheap Key West to Chicago flight deals from over hundreds of airlines.
Our extensive search allows you to compare prices from over 500 airlines to choose the cheapest flight tickets from Key West to Chicago. The cheapest airline operating is United Airlines.
3
Set up a Price Alert
By setting up a Price Alert for your Key West to Chicago route, you can easily track the price of your airline tickets from without manually checking every day.
4
Don't miss cheap Key West to Chicago flight deals and promo codes.
You can always get the latest deals through Trip.com Deals and Promo Codes for cheap flights. If registering a free membership, you can receive more deals for your flights.
5
Book early or wait unitl the last minute.
It's always better to book early. Flight tickets tend to be the cheapest when they are first released, normally about a year before the departure date. So, check online as soon as the flights you want become available. If you miss the cheapest time, you can still find lower-priced tickets as the flight date approaches.
6
Search for flights on the go.
To get the best flight booking experience on the go, download Trip.com and search for cheap flight tickets from Key West to Chicago to get exclusive deals for you.

Flight Info | Key West to Chicago

Cheapest direct flight price€104
Cheapest return ticket price€253
Off-season for travelDecember
Peak season for travelNovember
Flight distance2,001.04 km
Average flight time5 hours 52 minutes
Popular airlineSilver Airways

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