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Owen Roberts International Airport to Chicago flight
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Cheap Flights from Owen Roberts International Airport to Chicago

Search for flights from Owen Roberts International Airport to Chicago and check out affordable one-way and round-trip options.

  • One way
  • Round-trip
sortSort by: Lowest Price
  • Sort by: Lowest Price
  • Sort by: Earliest Flight
      • GCM11:30
        7h 48m
        1 stop
        MDW19:18
        Grand Cayman - Chicago|Tue, Jun 25|Cayman Airways
        AU$388AU$532
        27% OFF
        27% OFF
        AU$532AU$388
      • GCM16:45
        25h 42m
        1 stop
        MDW18:27
        Grand Cayman - Chicago|Thu, May 30|Cayman Airways
        AU$389AU$532
        27% OFF
        27% OFF
        AU$532AU$389
      • GCM16:45
        24h 25m
        1 stop
        MDW17:10
        Grand Cayman - Chicago|Fri, May 17|Cayman Airways
        AU$390AU$532
        27% OFF
        27% OFF
        AU$532AU$390
      • GCM16:45
        26h 33m
        1 stop
        MDW19:18
        Grand Cayman - Chicago|Mon, Jul 1|Cayman Airways
        AU$391
        AU$391
      • GCM16:45
        14h 46m
        1 stop
        MDW07:31
        Grand Cayman - Chicago|Thu, Jun 27|Cayman Airways
        AU$394
        AU$394
      • GCM14:00
        28h 27m
        1 stop
        MDW18:27
        Grand Cayman - Chicago|Sun, May 19|Cayman Airways
        AU$419
        AU$419
      • GCM09:30
        8h 57m
        1 stop
        MDW18:27
        Grand Cayman - Chicago|Mon, May 13|Cayman Airways
        AU$447
        AU$447
      • GCM11:30
        13h 15m
        1 stop
        MDW00:45
        Grand Cayman - Chicago|Sun, May 26|Cayman Airways
        AU$448
        AU$448
      • GCM09:30
        8h 57m
        1 stop
        MDW18:27
        Grand Cayman - Chicago|Mon, May 20|Cayman Airways
        AU$456
        AU$456
      • GCM11:05
        12h 32m
        1 stop
        MDW23:37
        Grand Cayman - Chicago|Fri, Jun 21|Cayman Airways
        AU$457
        AU$457
      • GCM13:00
        3h 5m
        Direct
        CHI14:00
        Grand Cayman - Chicago|Sun, May 19|Cayman Airways
        Find More Flights
        Find More Flights

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

Selected Airlines from Owen Roberts International Airport to Chicago

See which airlines fly from Owen Roberts International Airport to Chicago. Find the airline that best meets your travel needs by comparing prices and treat yourself to an enjoyable journey.

Cayman Airways
From AU$388
United Airlines
From AU$486
Air Canada
From AU$493
American Airlines
From AU$512
Jetblue Airways
From AU$564
Delta Air Lines
From AU$573
WestJet
From AU$574
Southwest Airlines
From AU$642
ANA airlines
Find more flights and airlines

There are 2 airport(s) in Chicago. Discover the top routes now!

Learn about different airports in Chicago, find the best flight and transfer options, and plan your journey.

  • 24.74 km from downtown Chicago
    O'Hare International Airport
    Tickets From
    AU$456
  • 12.76 km from downtown ChicagoCheapestClosest
    Midway International Airport
    Tickets From
    AU$388
Flight Schedule from Owen Roberts International Airport to Chicago

Check the schedule for flights from Owen Roberts International Airport to Chicago and find the flight that best matches your travel plans.

Flight info.
Departure
Arrival
Weekly Schedule

  1. KX112

    Cayman Airways

    09:30

    GCM

    1.7h

    12:10

    MIA

    S------
    Search

  2. F92109

    Frontier Airlines

    17:08

    MIA

    3.2h

    19:18

    MDW

    ----T--

  3. KX112

    Cayman Airways

    09:30

    GCM

    1.7h

    12:10

    MIA

    S------
    Search

  4. F93179

    Frontier Airlines

    19:01

    MIA

    3.1h

    21:09

    MDW

    SMT---S

  5. B6766

    Jetblue Airways

    11:25

    GCM

    3.8h

    16:15

    JFK

    S-T--F-
    Search

  6. AA3354

    American Airlines

    20:30

    EWR

    2.8h

    22:16

    ORD

    SMTWTFS

  7. KX104

    Cayman Airways

    11:30

    GCM

    1.7h

    14:10

    MIA

    -MT----
    Search

  8. AA791

    American Airlines

    19:01

    MIA

    3.5h

    21:28

    ORD

    SMTWTFS

  9. KX104

    Cayman Airways

    11:30

    GCM

    1.7h

    14:10

    MIA

    -MT----
    Search

  10. AA1788

    American Airlines

    17:17

    MIA

    3.4h

    19:39

    ORD

    SMTWTFS

  11. KX104

    Cayman Airways

    11:30

    GCM

    1.7h

    14:10

    MIA

    -MT----
    Search

  12. F92109

    Frontier Airlines

    17:08

    MIA

    3.2h

    19:18

    MDW

    ----T--

  13. KX104

    Cayman Airways

    11:30

    GCM

    1.7h

    14:10

    MIA

    -MT----
    Search

  14. UA2621

    United Airlines

    16:06

    MIA

    3.6h

    18:41

    ORD

    SMTWTFS

  15. KX108

    Cayman Airways

    14:00

    GCM

    1.7h

    16:40

    MIA

    ------S
    Search

  16. AA791

    American Airlines

    19:01

    MIA

    3.5h

    21:28

    ORD

    SMTWTFS

  17. KX202

    Cayman Airways

    14:00

    GCM

    1.8h

    16:50

    TPA

    S--W---
    Search

  18. F91185

    Frontier Airlines

    17:05

    TPA

    2.7h

    18:48

    MDW

    ---W-F-

  19. AA367

    American Airlines

    14:15

    GCM

    1.6h

    16:50

    MIA

    SMTWTFS
    Search

  20. AA791

    American Airlines

    19:01

    MIA

    3.5h

    21:28

    ORD

    SMTWTFS
Find more flights and airlines

Flight Info of Flights from Owen Roberts International Airport to Chicago

Cheapest round-trip ticket price

AU$899

Cheapest nonstop flight price

AU$388

Off-season for travel

January

Peak season for travel

November

FAQs for Owen Roberts International Airport to Chicago Flights

  • 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. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14km. It takes about 30 minutes by taxi.

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