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Cheap flight deals from Chicago to Grand Cayman Starting at IDR 2,160,646

For as little as IDR 2,160,646, you can take your next adventure to Grand Cayman without breaking the bank. Choose between one-way and return tickets from Chicago below.

  • One way
  • Round-trip
      • MDW06:00
        10h 10m
        1 stop
        GCM16:10
        Tue, Apr 1|Chicago - Grand Cayman|Frontier Airlines
        IDR 2,160,646IDR 3,543,904
        39% OFF
        39% OFF
        IDR 3,543,904IDR 2,160,646

        Choose Frontier Airlines flights from Chicago to Grand Cayman. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Tue, Apr 1, arriving at Owen Roberts International Airport. One-way Prices start from IDR 2,160,646 including taxes and charges.

      • MDW07:25
        7h 45m
        1 stop
        GCM16:10
        Tue, Mar 4|Chicago - Grand Cayman|Frontier Airlines
        IDR 2,328,921IDR 3,543,904
        34% OFF
        34% OFF
        IDR 3,543,904IDR 2,328,921

        Choose Frontier Airlines flights from Chicago to Grand Cayman. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Tue, Mar 4, arriving at Owen Roberts International Airport. One-way Prices start from IDR 2,328,921 including taxes and charges.

      • MDW07:25
        7h 45m
        1 stop
        GCM16:10
        Wed, Feb 19|Chicago - Grand Cayman|Frontier Airlines
        IDR 2,333,408IDR 3,543,904
        34% OFF
        34% OFF
        IDR 3,543,904IDR 2,333,408

        Choose Frontier Airlines flights from Chicago to Grand Cayman. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Wed, Feb 19, arriving at Owen Roberts International Airport. One-way Prices start from IDR 2,333,408 including taxes and charges.

      • MDW07:25
        7h 55m
        1 stop
        GCM16:20
        Wed, Mar 5|Chicago - Grand Cayman|Frontier Airlines
        IDR 2,355,845
        IDR 2,355,845

        Choose Frontier Airlines flights from Chicago to Grand Cayman. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Wed, Mar 5, arriving at Owen Roberts International Airport. One-way Prices start from IDR 2,355,845 including taxes and charges.

      • ORD10:05
        25h 2m
        1 stop
        GCM12:07
        Wed, Feb 19|Chicago - Grand Cayman|Delta Air Lines
        IDR 2,445,591
        IDR 2,445,591

        Choose Delta Air Lines flights from Chicago to Grand Cayman. The one-way connecting flight with Delta Air Lines departs from O'Hare International Airport on Wed, Feb 19, arriving at Owen Roberts International Airport. One-way Prices start from IDR 2,445,591 including taxes and charges.

      • ORD17:40
        17h 27m
        1 stop
        GCM12:07
        Wed, Feb 19|Chicago - Grand Cayman|Jetblue Airways
        IDR 2,485,977
        IDR 2,485,977

        Choose Jetblue Airways flights from Chicago to Grand Cayman. The one-way connecting flight with Jetblue Airways departs from O'Hare International Airport on Wed, Feb 19, arriving at Owen Roberts International Airport. One-way Prices start from IDR 2,485,977 including taxes and charges.

      • MDW19:25
        19h 45m
        1 stop
        GCM16:10
        Mon, Mar 3|Chicago - Grand Cayman|Frontier Airlines
        IDR 2,542,069
        IDR 2,542,069

        Choose Frontier Airlines flights from Chicago to Grand Cayman. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Mon, Mar 3, arriving at Owen Roberts International Airport. One-way Prices start from IDR 2,542,069 including taxes and charges.

      • MDW19:25
        19h 45m
        1 stop
        GCM16:10
        Mon, Feb 17|Chicago - Grand Cayman|Frontier Airlines
        IDR 2,631,815
        IDR 2,631,815

        Choose Frontier Airlines flights from Chicago to Grand Cayman. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Mon, Feb 17, arriving at Owen Roberts International Airport. One-way Prices start from IDR 2,631,815 including taxes and charges.

      • MDW07:25
        6h 59m
        1 stop
        GCM15:24
        Thu, Mar 6|Chicago - Grand Cayman|Frontier Airlines
        IDR 2,880,862
        IDR 2,880,862

        Choose Frontier Airlines flights from Chicago to Grand Cayman. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Thu, Mar 6, arriving at Owen Roberts International Airport. One-way Prices start from IDR 2,880,862 including taxes and charges.

      • MDW07:25
        7h 55m
        1 stop
        GCM16:20
        Sun, Mar 2|Chicago - Grand Cayman|Frontier Airlines
        IDR 2,880,862
        IDR 2,880,862

        Choose Frontier Airlines flights from Chicago to Grand Cayman. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Sun, Mar 2, arriving at Owen Roberts International Airport. One-way Prices start from IDR 2,880,862 including taxes and charges.

      • CHI01:00 pm
        3h 5m
        Nonstop
        GCM02:00 pm
        Thu, Feb 20|Chicago - Grand Cayman|Frontier 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 Grand Cayman flight time & flight schedules

Flight info.
Departure
Arrival
Weekly Schedule

  1. AA2842

    American Airlines

    05:00

    ORD

    2.1h

    08:07

    CLT

    SMTWTFS
    Search

  2. AA301

    American Airlines

    09:20

    CLT

    3.0h

    11:20

    GCM

    SMTWTFS

  3. F91186

    Frontier Airlines

    06:50

    MDW

    2.8h

    10:36

    TPA

    S-TWTFS
    Search

  4. KX201

    Cayman Airways

    15:25

    TPA

    1.8h

    16:10

    GCM

    S---TFS

  5. AA1411

    American Airlines

    06:51

    ORD

    3.1h

    11:00

    MIA

    SMTWTFS
    Search

  6. KX105

    Cayman Airways

    15:30

    MIA

    1.7h

    16:10

    GCM

    SMTW---

  7. F92110

    Frontier Airlines

    09:16

    MDW

    3.2h

    13:30

    MIA

    S--WTF-
    Search

  8. KX109

    Cayman Airways

    18:00

    MIA

    1.7h

    18:40

    GCM

    ------S

  9. F92110

    Frontier Airlines

    09:16

    MDW

    3.2h

    13:30

    MIA

    S--WTF-
    Search

  10. AA956

    American Airlines

    12:05

    MIA

    1.8h

    13:55

    GCM

    SMTWTFS

  11. F92456

    Frontier Airlines

    14:16

    MDW

    3.1h

    18:22

    MIA

    -MTW-FS
    Search

  12. KX105

    Cayman Airways

    15:30

    MIA

    1.7h

    16:10

    GCM

    SMTW---

  13. F92456

    Frontier Airlines

    14:16

    MDW

    3.1h

    18:22

    MIA

    -MTW-FS
    Search

  14. AA956

    American Airlines

    12:05

    MIA

    1.8h

    13:55

    GCM

    SMTWTFS

  15. F91416

    Frontier Airlines

    16:02

    ORD

    2.9h

    19:55

    TPA

    SMTWTFS
    Search

  16. KX203

    Cayman Airways

    16:30

    TPA

    1.8h

    17:20

    GCM

    S--W---

  17. F91416

    Frontier Airlines

    16:02

    ORD

    2.9h

    19:55

    TPA

    SMTWTFS
    Search

  18. KX205

    Cayman Airways

    15:00

    TPA

    1.8h

    15:45

    GCM

    ----T--

  19. F91416

    Frontier Airlines

    16:02

    ORD

    2.9h

    19:55

    TPA

    SMTWTFS
    Search

  20. KX201

    Cayman Airways

    15:25

    TPA

    1.8h

    16:10

    GCM

    S---TFS
Find more flights and airlines

When is the cheapest time to fly from Chicago to Grand Cayman?

Price trend charts are a great way of tracking how much your flights cost in the lead up to departure and can help you choose when to book your tickets. See how prices to Grand Cayman from Chicago have changed and are set to move below.

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 Grand Cayman (GCM) the cheapest?

    Airlines adjust prices for flights from Chicago to Grand Cayman 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 Chicago (CHI) to Grand Cayman (GCM) cost?

    According to Trip.com's data, the lowest price is around IDR 8,961,184.

  • How long does it take to fly from Chicago (CHI) to Grand Cayman (GCM)?

    It takes about 4 hours 6 minutes to fly from Chicago (CHI) to Grand Cayman (GCM).

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

    • The distance from Owen Roberts International Airport to downtown is about 11 km, by taxi about 30 minutes.

  • What are the most popular airlines that fly from Chicago (CHI) to Grand Cayman (GCM)?

    Airlines with flights from Chicago (CHI) to Grand Cayman (GCM): American Airlines and United Airlines.

  • What's the most popular airline for non-stop flights from Chicago (CHI) to Grand Cayman (GCM)?

    United Airlines operates 1 non-stop flights from Chicago (CHI) to Grand Cayman (GCM).

  • How many airports are there in Grand Cayman (GCM)?

    There are 1 airport(s) near Grand Cayman (GCM): Owen Roberts International Airport.

How to find a cheap flight from Chicago to Grand Cayman

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
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 Grand Cayman

Cheapest direct flight priceIDR 2,160,646
Cheapest return ticket priceIDR 8,887,143
Off-season for travelMarch
Peak season for travelNovember
Flight distance2,580.07 km
Average flight time4 hours 6 minutes
Popular airlineAmerican Airlines

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