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Cheap flights from Chicago (CHI) to Grand Cayman from $276

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/3. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
CHI — GCM
May 12 — May 191
From?
To?
Sun 5/12
Sun 5/19
1 adult, Economy
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How far in advance should I book a flight from Chicago to Grand Cayman?

Find a great deal and save up to 81% by booking at least 22 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago to Grand Cayman within the next two weeks, with the cheapest ticket starting at $671.

What is the cheapest month to fly from Chicago to Grand Cayman?

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, October can be a great choice for travel to Grand Cayman. Flights to Grand Cayman from Chicago in October are about $577 on average during October, but can be found for as low as $380.

When is the cheapest time to fly from Chicago to Grand Cayman (CHI - LAW)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Grand Cayman as you normally would.

Cheap Air Canada flights from Chicago to Grand Cayman

Explore cheap flight options specifically provided by Air Canada for the route between Chicago and Grand Cayman. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,689,106 searches. Data last updated May 7, 2024.
Take a peek at the cheapest Air Canada flights we've detected traveling from Chicago to Grand Cayman. Come back soon if you're not finding the exact deal you're looking for.
Sun 6/96:00 amORD - GCM
1 stop8h 35mAir Canada
Sun 6/163:45 pmGCM - ORD
1 stop18h 09mAir Canada
Deal found 5/6$468
Sun 6/96:00 amORD - GCM
1 stop8h 35mAir Canada
Sun 6/163:45 pmGCM - ORD
2 stops18h 16mAir Canada
Deal found 5/6$475
Wed 5/291:55 pmORD - GCM
2 stops24h 40mAir Canada
Thu 6/63:45 pmGCM - ORD
1 stop18h 09mAir Canada
Deal found 5/6$476
Wed 5/291:55 pmORD - GCM
2 stops24h 40mAir Canada
Thu 6/63:45 pmGCM - ORD
2 stops16h 15mAir Canada
Deal found 5/6$477
Tue 6/116:30 pmORD - GCM
2 stops44h 05mAir Canada
Sun 6/163:45 pmGCM - ORD
2 stops18h 16mAir Canada
Deal found 5/6$521
Sat 8/34:00 pmORD - GCM
1 stop22h 35mAir Canada
Thu 8/83:45 pmGCM - ORD
1 stop18h 09mAir Canada
Deal found 5/5$544
Thu 8/156:00 amORD - GCM
1 stop8h 35mAir Canada
Thu 8/223:45 pmGCM - ORD
2 stops18h 16mAir Canada
Deal found 5/6$555
Sat 8/36:34 pmORD - GCM
2 stops20h 01mAir Canada
Thu 8/83:45 pmGCM - ORD
1 stop18h 09mAir Canada
Deal found 5/5$556
Thu 8/86:00 amORD - GCM
1 stop8h 35mAir Canada
Sun 8/113:45 pmGCM - ORD
1 stop18h 09mAir Canada
Deal found 5/6$566

Cheap Delta flights from Chicago to Grand Cayman

Explore cheap flight options specifically provided by Delta for the route between Chicago and Grand Cayman. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,689,106 searches. Data last updated May 7, 2024.
Take a gander at the lowest prices we've found on Delta flights from Chicago to Grand Cayman. Check back soon if you're not seeing flights that suit your needs.
Wed 6/56:00 amMDW - GCM
1 stop5h 31mDelta
Wed 6/1212:55 pmGCM - MDW
1 stop8h 51mDelta
Deal found 5/6$578
Fri 8/166:00 amORD - GCM
1 stop5h 30mDelta
Fri 8/2312:50 pmGCM - ORD
1 stop11h 09mDelta
Deal found 5/6$603
Tue 6/116:00 amMDW - GCM
1 stop5h 35mDelta
Sun 6/1612:55 pmGCM - MDW
2 stops19h 53mDelta
Deal found 5/6$608
Sat 8/176:00 amORD - GCM
1 stop5h 30mDelta
Sat 8/2412:50 pmGCM - ORD
1 stop11h 09mDelta
Deal found 5/6$628
Sat 8/176:00 amORD - GCM
1 stop5h 30mDelta
Sat 8/2412:50 pmGCM - ORD
2 stops18h 32mDelta
Deal found 5/6$633
Fri 10/256:50 pmMDW - GCM
1 stop16h 40mDelta
Sun 10/2712:50 pmGCM - MDW
1 stop8h 54mDelta
Deal found 5/5$635
Wed 5/296:00 amMDW - GCM
1 stop5h 26mDelta
Thu 6/612:51 pmGCM - MDW
1 stop9h 10mDelta
Deal found 5/6$663
Wed 5/295:40 amORD - GCM
1 stop5h 46mDelta
Thu 5/3012:51 pmGCM - ORD
1 stop8h 36mDelta
Deal found 5/6$748
Wed 5/295:40 amORD - GCM
1 stop5h 46mDelta
Thu 5/3012:51 pmGCM - ORD
2 stops18h 49mDelta
Deal found 5/6$753

Cheap Chicago to Grand Cayman flights in May & June 2024

Find cheap flight options from Chicago to Grand Cayman specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,689,106 searches. Prices were last updated on May 7, 2024.
These are some of the most attractive deals on flights from Chicago to Grand Cayman in 2024. Check back soon for alternative fares.
Tue 5/289:15 pmORD - GCM
1 stop18h 55mMultiple Airlines
Fri 5/314:45 pmGCM - ORD
1 stop26h 48mMultiple Airlines
Deal found 5/5$418
Wed 6/58:50 pmORD - GCM
1 stop24h 30mMultiple Airlines
Wed 6/1211:30 amGCM - ORD
1 stop21h 34mMultiple Airlines
Deal found 5/6$432
Tue 6/118:50 pmORD - GCM
1 stop19h 20mMultiple Airlines
Sun 6/162:00 pmGCM - ORD
1 stop19h 04mMultiple Airlines
Deal found 5/6$466
Sun 6/96:00 amORD - GCM
1 stop8h 35mAir Canada
Sun 6/163:45 pmGCM - ORD
1 stop18h 09mAir Canada
Deal found 5/6$468
Sun 6/96:00 amORD - GCM
1 stop8h 35mAir Canada
Sun 6/163:45 pmGCM - ORD
2 stops18h 16mAir Canada
Deal found 5/6$475
Wed 5/291:55 pmORD - GCM
2 stops24h 40mAir Canada
Thu 6/63:45 pmGCM - ORD
1 stop18h 09mAir Canada
Deal found 5/6$476
Wed 5/291:55 pmORD - GCM
2 stops24h 40mAir Canada
Thu 6/63:45 pmGCM - ORD
2 stops16h 15mAir Canada
Deal found 5/6$477
Tue 6/118:50 pmORD - GCM
1 stop19h 20mMultiple Airlines
Sun 6/165:10 pmGCM - ORD
2 stops25h 02mMultiple Airlines
Deal found 5/6$481
Tue 6/117:36 pmMDW - GCM
1 stop20h 34mMultiple Airlines
Sun 6/162:00 pmGCM - MDW
1 stop17h 31mMultiple Airlines
Deal found 5/6$481

Chicago to Grand Cayman 2024 flight deals

Discover exclusive flight deals for travel between Chicago and Grand Cayman in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,689,106 searches. Data last updated May 7, 2024.
These are some of the most attractive deals on flights from Chicago to Grand Cayman in 2024. Check back soon for alternative fares.
Tue 5/289:15 pmORD - GCM
1 stop18h 55mMultiple Airlines
Fri 5/314:45 pmGCM - ORD
1 stop26h 48mMultiple Airlines
Deal found 5/5$418
Wed 6/58:50 pmORD - GCM
1 stop24h 30mMultiple Airlines
Wed 6/1211:30 amGCM - ORD
1 stop21h 34mMultiple Airlines
Deal found 5/6$432
Tue 6/118:50 pmORD - GCM
1 stop19h 20mMultiple Airlines
Sun 6/162:00 pmGCM - ORD
1 stop19h 04mMultiple Airlines
Deal found 5/6$466
Sun 6/96:00 amORD - GCM
1 stop8h 35mAir Canada
Sun 6/163:45 pmGCM - ORD
1 stop18h 09mAir Canada
Deal found 5/6$468
Sun 6/96:00 amORD - GCM
1 stop8h 35mAir Canada
Sun 6/163:45 pmGCM - ORD
2 stops18h 16mAir Canada
Deal found 5/6$475
Wed 5/291:55 pmORD - GCM
2 stops24h 40mAir Canada
Thu 6/63:45 pmGCM - ORD
1 stop18h 09mAir Canada
Deal found 5/6$476
Wed 5/291:55 pmORD - GCM
2 stops24h 40mAir Canada
Thu 6/63:45 pmGCM - ORD
2 stops16h 15mAir Canada
Deal found 5/6$477
Tue 6/118:50 pmORD - GCM
1 stop19h 20mMultiple Airlines
Sun 6/165:10 pmGCM - ORD
2 stops25h 02mMultiple Airlines
Deal found 5/6$481
Tue 6/117:36 pmMDW - GCM
1 stop20h 34mMultiple Airlines
Sun 6/162:00 pmGCM - MDW
1 stop17h 31mMultiple Airlines
Deal found 5/6$481

Non-stop flights to Grand Cayman from Chicago

Discover non-stop flight options from Chicago to Grand Cayman. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,689,106 searches. Data last updated May 7, 2024.
For a shorter flight, select one of these non-stop flights from Chicago to Grand Cayman. Select from other flights from Chicago to Grand Cayman by using the search form above.
Sat 6/89:28 amORD - GCM
Nonstop4h 02mUnited Airlines
Sat 6/151:50 pmGCM - ORD
Nonstop4h 12mUnited Airlines
Deal found 5/7$704
Sun 5/268:53 amORD - GCM
Nonstop4h 02mUnited Airlines
Sun 6/22:05 pmGCM - ORD
Nonstop4h 10mUnited Airlines
Deal found 5/7$814
Sun 6/98:53 amORD - GCM
Nonstop4h 02mUnited Airlines
Sun 6/162:05 pmGCM - ORD
Nonstop4h 10mUnited Airlines
Deal found 5/6$1,467
Sun 6/98:53 amORD - GCM
Nonstop4h 02mUnited Airlines
Sun 6/162:05 pmGCM - ORD
Nonstop4h 10mUnited Airlines
Deal found 5/6$2,356

Chicago to Grand Cayman flights leaving soon

Find last-minute flight options from Chicago to Grand Cayman for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,689,106 searches. Data last updated May 7, 2024.
Check out these flights departing soon from Chicago to Grand Cayman. Users should be sure to double check the price, date, and time of their last-minute flight.
Tue 5/147:13 pmMDW - GCM
1 stop20h 57mMultiple Airlines
Sat 5/1811:30 amGCM - MDW
1 stop12h 39mMultiple Airlines
Deal found 5/7$552
Fri 5/177:23 pmMDW - GCM
2 stops19h 27mMultiple Airlines
Fri 5/247:00 amGCM - MDW
1 stop11h 27mMultiple Airlines
Deal found 5/6$625
Thu 5/1610:03 amORD - GCM
1 stop11h 17mMultiple Airlines
Sat 5/189:10 amGCM - ORD
2 stops15h 22mMultiple Airlines
Deal found 5/6$634
Thu 5/169:03 amORD - GCM
1 stop12h 17mMultiple Airlines
Sat 5/1811:30 amGCM - ORD
1 stop21h 12mMultiple Airlines
Deal found 5/6$645
Thu 5/166:22 pmMDW - GCM
1 stop21h 23mMultiple Airlines
Sat 5/1811:30 amGCM - MDW
1 stop12h 39mMultiple Airlines
Deal found 5/6$720
Thu 5/166:00 amORD - GCM
1 stop8h 35mMultiple Airlines
Mon 5/206:10 pmGCM - ORD
2 stops27h 54mMultiple Airlines
Deal found 5/6$748
Tue 5/147:13 pmMDW - GCM
1 stop20h 57mMultiple Airlines
Sat 5/189:10 amGCM - MDW
2 stops12h 26mMultiple Airlines
Deal found 5/7$832
Thu 5/167:35 amORD - GCM
2 stops13h 45mMultiple Airlines
Sat 5/1811:30 amGCM - ORD
2 stops11h 59mMultiple Airlines
Deal found 5/6$846
Fri 5/176:48 pmMDW - GCM
1 stop16h 38mDelta
Fri 5/2412:51 pmGCM - MDW
1 stop9h 10mDelta
Deal found 5/6$868

One-way flights to Grand Cayman from Chicago

Search for one-way flight options from Chicago to Grand Cayman. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,689,106 searches. Data last updated May 7, 2024.
If you're seeking multiple options on one-way flights from Chicago to Grand Cayman, be sure to check out these deals, which are updated often. Those seeking round-trip flights from Chicago to Grand Cayman should utilize the search form at the the top of the page.
Sun 11/37:00 amORD - GCM
1 stop5h 50mAmerican Airlines
Deal found 5/7$276
Sun 11/38:25 pmORD - GCM
2 stops14h 20mAmerican Airlines
Deal found 5/7$326
Sun 5/197:35 amORD - GCM
2 stops11h 05mMultiple Airlines
Deal found 5/5$358
Sun 5/195:33 pmORD - GCM
3 stops27h 47mMultiple Airlines
Deal found 5/5$411
Sun 5/195:00 amORD - GCM
1 stop5h 55mAmerican Airlines
Deal found 5/5$597
Fri 5/176:00 amORD - GCM
1 stop6h 35mUnited Airlines
Deal found 5/6$602
Sun 5/195:15 amORD - GCM
2 stops7h 50mAmerican Airlines
Deal found 5/5$626
Sun 5/199:20 pmORD - GCM
1 stop17h 40mUnited Airlines
Deal found 5/6$646
Fri 5/173:29 pmORD - GCM
2 stops19h 26mAmerican Airlines
Deal found 5/6$682

Find flights from Chicago to Grand Cayman within your budget

Customize your flight search to find flights from Chicago to Grand Cayman that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,689,106 searches. Data last updated May 7, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$418 - $593

Route

Depart

Return

Price

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 5/28

1 stop18h 55m

George Town Owen Roberts Intl

Fri 5/31

1 stop26h 48m

$418

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 6/5

1 stop24h 30m

George Town Owen Roberts Intl

Wed 6/12

1 stop21h 34m

$432

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 6/11

1 stop19h 20m

George Town Owen Roberts Intl

Sun 6/16

1 stop19h 04m

$466

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 6/9

1 stop8h 35m

George Town Owen Roberts Intl

Sun 6/16

1 stop18h 09m

$468

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 6/9

1 stop8h 35m

George Town Owen Roberts Intl

Sun 6/16

2 stops18h 16m

$475

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 5/29

2 stops24h 40m

George Town Owen Roberts Intl

Thu 6/6

1 stop18h 09m

$476

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Wed 6/5

1 stop5h 31m

George Town Owen Roberts Intl

Wed 6/12

1 stop8h 51m

$578

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 8/3

2 stops14h 33m

George Town Owen Roberts Intl

Thu 8/8

2 stops10h 21m

$581

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 6/11

1 stop15h 04m

George Town Owen Roberts Intl

Sun 6/16

Nonstop4h 10m

$593

Flights are sorted by cheapest first

Deals found on 5/5

No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Grand Cayman

Get insights into the airlines that provide service to Grand Cayman. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Grand Cayman. Reviews last updated May 7, 2024.
Get a feel of what it's like to fly with Air Canada, Delta and United Airlines from Chicago to Grand Cayman by reading reviews from past customers. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.1
Very good
10,818 reviews
Check prices

Food

7.4

Comfort

7.9

Entertainment

8.0

Crew

8.6

Overall

8.1

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Delta
8.1
Very good
10,818 reviews
Delta
8.1
Very good
10,818 reviews
Check prices

Food

7.4

Comfort

7.9

Entertainment

8.0

Crew

8.6

Overall

8.1

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

WestJet
7.6
Good
2,948 reviews
Delta
8.1
Very good
10,818 reviews
Check prices

Food

7.4

Comfort

7.9

Entertainment

8.0

Crew

8.6

Overall

8.1

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

United Airlines
7.4
Good
11,090 reviews
Delta
8.1
Very good
10,818 reviews
Check prices

Food

7.4

Comfort

7.9

Entertainment

8.0

Crew

8.6

Overall

8.1

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

American Airlines
7.3
Good
14,697 reviews
Delta
8.1
Very good
10,818 reviews
Check prices

Food

7.4

Comfort

7.9

Entertainment

8.0

Crew

8.6

Overall

8.1

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Air Canada
7.0
Good
6,915 reviews
Delta
8.1
Very good
10,818 reviews
Check prices

Food

7.4

Comfort

7.9

Entertainment

8.0

Crew

8.6

Overall

8.1

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Grand Cayman. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find flights from Chicago to Grand Cayman for under $500 on Cheapflights?

    Yes, there are multiple flights from Chicago to Grand Cayman for under $500. The cheapest flight booked recently is on Multiple Airlines for just $418, but on average you can expect to pay $497.

  • Are there nonstop flights from Chicago to Grand Cayman for under $800 on Cheapflights?

    Cheapflights has at least 4 direct flights from Chicago to Grand Cayman under $800. A good price for a nonstop flight from Chicago to Grand Cayman is less than $1,335.

  • Are there last-minute flights available from Chicago to Grand Cayman for under $600?

    There are currently 17+ open flights from Chicago to Grand Cayman within the next 7 days for less than $600.

  • What are the cheapest airlines to fly from Chicago to Grand Cayman one-way?

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $276. Users have also found prices from $602 and $6,174 on United Airlines and British Airways, respectively.

  • What are the most popular airlines that fly from Chicago to Grand Cayman?

    Before booking your flight from Chicago to Grand Cayman check out the most popular airlines for this route: American Airlines, Delta or Linear Air Taxi.

  • What are the cheapest flights from Chicago to Grand Cayman?

    On average you can expect to pay $598 for a flight from Chicago to Grand Cayman. The cheapest flight overall is $445 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $418.

  • What does ORD to GCM mean?

    Chicago O'Hare Intl Airport is ORD and George Town Owen Roberts Intl Airport is GCM. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are some additional IATA codes for airports related to your trip.

  • Can I find deals for flights from Chicago to Grand Cayman that include extra baggage allowance?

    The amount of baggage you can bring on your Chicago to Grand Cayman flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Grand Cayman with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Grand Cayman flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Chicago to Grand Cayman that include hotel bookings?

    Yes. In addition to deals on Chicago to Grand Cayman flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Grand Cayman?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Grand Cayman.

  • Can I find deals for business class flights from Chicago to Grand Cayman?

    Yes. Cheapflights offers flight deals from Chicago to Grand Cayman by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Chicago to Grand Cayman that allow pets onboard?

    Many airlines flying from Chicago to Grand Cayman offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Grand Cayman?

    Yes, you can often find last-minute deals on Chicago to Grand Cayman flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to Grand Cayman flight deals updated?

    The Chicago to Grand Cayman flight deals you see on this page were last updated on 5/6.

See more FAQs

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Alternative routes for Chicago to Grand Cayman
See prices for flight routes from nearby airports that may be better suited for you.

O'Hare Intl to George Town flights
Midway to George Town flights
St. Louis to George Town flights
Moline to George Town flights
O'Hare Intl to Cayman Brac flights

Top 4 airlines flying from Chicago to Grand Cayman

Discover the top 4 airlines that operate flights from Chicago to Grand Cayman. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,689,106 searches. Data last updated May 7, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$351Average$545FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
American AirlinesCheapest$372Average$589FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
United AirlinesCheapest$401Average$644FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Linear Air TaxiCheapest$18,288Average$51,983FlexibilityNo cancel feeOn-timeN/A
Search Linear Air Taxi flights
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Search flights from Chicago to Grand Cayman by cabin class

Find flights from Chicago to Grand Cayman, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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Business Class
Prem Econ Class
Economy Class

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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Chicago to Grand Cayman?

Deals for Chicago to Grand Cayman flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Chicago to Grand Cayman?

Cheapflights helps you find that perfect flight to Grand Cayman from Chicago by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Chicago to Grand Cayman with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Chicago to Grand Cayman, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Chicago to Grand Cayman become cheaper?

Yes! Start tracking prices for Chicago to Grand Cayman flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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