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Cheap flights from the Cayman Islands to Chicago (CHI) from $327

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 7/21. 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.
GCM — CHI
May 11 — May 181
From?
To?
Sat 5/11
Sat 5/18
1 adult, Economy
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What is the cheapest month to fly from Cayman Islands to Chicago?

November is one of the best times of the year to fly to Chicago from Cayman Islands. Prices for November average $577 per person but you can even find prices for as low as $373. The most expensive prices can be found in the month of March. Opting for a November flight can save you 83% on your journey compared to booking in March

When is the cheapest time to fly from Cayman Islands to Chicago (KY - CHI)?

When flying from Cayman Islands to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap Air Canada flights from Cayman Islands to Chicago

Explore cheap flight options specifically provided by Air Canada for the route between Cayman Islands and Chicago. 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 2,719,943 searches. Data last updated May 6, 2024.
Take a look at some of the lowest-priced Air Canada flights heading from Cayman Islands to Chicago. Make sure to check back often as deals are often changing.
Sun 6/23:45 pmGCM - ORD
2 stops18h 16mAir Canada
Sat 6/82:15 pmORD - GCM
1 stop24h 20mAir Canada
Deal found 5/5$505
Sun 5/193:45 pmGCM - ORD
2 stops18h 16mAir Canada
Thu 5/236:00 amORD - GCM
1 stop8h 35mAir Canada
Deal found 5/5$509
Sun 6/23:45 pmGCM - ORD
2 stops27h 06mAir Canada
Sat 6/86:30 pmORD - GCM
2 stops20h 05mAir Canada
Deal found 5/5$593

Cheap Delta flights from Cayman Islands to Chicago

Explore cheap flight options specifically provided by Delta for the route between Cayman Islands and Chicago. 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 2,719,943 searches. Data last updated May 6, 2024.
Take a gander at the lowest prices we've found on Delta flights from Cayman Islands to Chicago. Deals are refreshing constantly so come back soon for more options.
Fri 8/212:50 pmGCM - ORD
1 stop8h 51mDelta
Mon 8/56:00 amORD - GCM
1 stop5h 30mDelta
Deal found 5/5$569
Fri 8/212:50 pmGCM - MDW
2 stops19h 50mDelta
Mon 8/56:00 amMDW - GCM
1 stop5h 30mDelta
Deal found 5/5$744
Fri 8/212:50 pmGCM - MDW
1 stop20h 24mDelta
Mon 8/56:00 amMDW - GCM
1 stop5h 30mDelta
Deal found 5/5$759
Mon 5/2012:51 pmGCM - MDW
1 stop9h 10mDelta
Tue 6/46:00 amMDW - GCM
1 stop5h 31mDelta
Deal found 5/5$1,136

Cheap Cayman Islands to Chicago flights in May & June 2024

Find cheap flight options from Cayman Islands to Chicago specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,719,943 searches. Prices were last updated on May 6, 2024.
These are some of the most attractive deals on flights from Cayman Islands to Chicago in 2024. Check back soon for alternative fares.
Mon 5/204:45 pmGCM - ORD
1 stop16h 00mMultiple Airlines
Tue 6/49:15 pmORD - GCM
1 stop18h 55mMultiple Airlines
Deal found 5/5$418
Mon 5/204:45 pmGCM - ORD
1 stop16h 00mMultiple Airlines
Tue 6/410:58 amORD - GCM
3 stops29h 12mMultiple Airlines
Deal found 5/5$432
Mon 5/209:30 amGCM - ORD
1 stop23h 15mMultiple Airlines
Mon 6/35:25 pmORD - GCM
1 stop22h 45mMultiple Airlines
Deal found 5/5$433
Mon 5/204:45 pmGCM - ORD
1 stop16h 00mMultiple Airlines
Tue 6/46:30 pmORD - GCM
2 stops44h 05mMultiple Airlines
Deal found 5/5$457
Mon 5/204:45 pmGCM - ORD
2 stops27h 50mMultiple Airlines
Tue 6/410:58 amORD - GCM
3 stops29h 12mMultiple Airlines
Deal found 5/5$466
Mon 5/204:45 pmGCM - ORD
3 stops27h 00mMultiple Airlines
Tue 6/410:58 amORD - GCM
3 stops29h 12mMultiple Airlines
Deal found 5/5$468
Mon 5/204:45 pmGCM - ORD
1 stop16h 00mMultiple Airlines
Mon 6/310:58 amORD - GCM
3 stops29h 12mMultiple Airlines
Deal found 5/5$469
Mon 5/204:45 pmGCM - ORD
1 stop16h 00mMultiple Airlines
Mon 6/37:35 amORD - GCM
2 stops8h 35mMultiple Airlines
Deal found 5/5$479
Mon 5/204:45 pmGCM - ORD
2 stops27h 50mMultiple Airlines
Mon 6/310:58 amORD - GCM
3 stops29h 12mMultiple Airlines
Deal found 5/5$503

Cayman Islands to Chicago 2024 flight deals

Discover exclusive flight deals for travel between Cayman Islands and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,719,943 searches. Data last updated May 6, 2024.
These are some of the most attractive deals on flights from Cayman Islands to Chicago in 2024. Check back soon for alternative fares.
Mon 5/204:45 pmGCM - ORD
1 stop16h 00mMultiple Airlines
Tue 6/49:15 pmORD - GCM
1 stop18h 55mMultiple Airlines
Deal found 5/5$418
Mon 5/204:45 pmGCM - ORD
1 stop16h 00mMultiple Airlines
Tue 6/410:58 amORD - GCM
3 stops29h 12mMultiple Airlines
Deal found 5/5$432
Mon 5/209:30 amGCM - ORD
1 stop23h 15mMultiple Airlines
Mon 6/35:25 pmORD - GCM
1 stop22h 45mMultiple Airlines
Deal found 5/5$433
Mon 5/204:45 pmGCM - ORD
1 stop16h 00mMultiple Airlines
Tue 6/46:30 pmORD - GCM
2 stops44h 05mMultiple Airlines
Deal found 5/5$457
Mon 5/204:45 pmGCM - ORD
2 stops27h 50mMultiple Airlines
Tue 6/410:58 amORD - GCM
3 stops29h 12mMultiple Airlines
Deal found 5/5$466
Mon 5/204:45 pmGCM - ORD
3 stops27h 00mMultiple Airlines
Tue 6/410:58 amORD - GCM
3 stops29h 12mMultiple Airlines
Deal found 5/5$468
Mon 5/204:45 pmGCM - ORD
1 stop16h 00mMultiple Airlines
Mon 6/310:58 amORD - GCM
3 stops29h 12mMultiple Airlines
Deal found 5/5$469
Mon 5/204:45 pmGCM - ORD
1 stop16h 00mMultiple Airlines
Mon 6/37:35 amORD - GCM
2 stops8h 35mMultiple Airlines
Deal found 5/5$479
Mon 5/204:45 pmGCM - ORD
2 stops27h 50mMultiple Airlines
Mon 6/310:58 amORD - GCM
3 stops29h 12mMultiple Airlines
Deal found 5/5$503

Non-stop flights to Chicago from Cayman Islands

Discover non-stop flight options from Cayman Islands to Chicago. 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 2,719,943 searches. Data last updated May 6, 2024.
Consider booking one of these non-stop flights heading from Cayman Islands to Chicago. Users seeking other options on flights from Cayman Islands to Chicago should update the search form at the top of the page.
Sun 6/22:05 pmGCM - ORD
Nonstop4h 10mUnited Airlines
Sat 6/89:28 amORD - GCM
Nonstop4h 02mUnited Airlines
Deal found 5/5$694

One-way flights to Chicago from Cayman Islands

Search for one-way flight options from Cayman Islands to Chicago. 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 2,719,943 searches. Data last updated May 6, 2024.
If you're seeking multiple options on one-way flights from Cayman Islands to Chicago, be sure to check out these deals, which are updated often. Those seeking round-trip flights from Cayman Islands to Chicago should utilize the search form at the the top of the page.
Sun 7/213:45 pmGCM - ORD
1 stop18h 09mAir Canada
Deal found 5/5$327
Sun 7/213:45 pmGCM - ORD
2 stops22h 55mAir Canada
Deal found 5/5$352
Sun 7/212:05 pmGCM - ORD
Nonstop4h 10mUnited Airlines
Deal found 5/5$396
Sun 7/2111:30 amGCM - ORD
3 stops20h 33mMultiple Airlines
Deal found 5/5$519

Find flights from Cayman Islands to Chicago within your budget

Customize your flight search to find flights from Cayman Islands to Chicago 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 2,719,943 searches. Data last updated May 6, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$418 - $690

Route

Depart

Return

Price

George Town Owen Roberts IntlChicago O'Hare Intl

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 5/20

1 stop16h 00m

Chicago O'Hare Intl

Tue 6/4

1 stop18h 55m

$418

George Town Owen Roberts IntlChicago O'Hare Intl

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 5/20

1 stop16h 00m

Chicago O'Hare Intl

Tue 6/4

3 stops29h 12m

$432

George Town Owen Roberts IntlChicago O'Hare Intl

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 5/20

1 stop23h 15m

Chicago O'Hare Intl

Mon 6/3

1 stop22h 45m

$433

George Town Owen Roberts IntlChicago O'Hare Intl

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 5/20

1 stop16h 00m

Chicago O'Hare Intl

Tue 6/4

2 stops44h 05m

$457

George Town Owen Roberts IntlChicago O'Hare Intl

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sun 6/2

2 stops18h 16m

Chicago O'Hare Intl

Sat 6/8

1 stop24h 20m

$505

George Town Owen Roberts IntlChicago O'Hare Intl

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sun 5/19

2 stops18h 16m

Chicago O'Hare Intl

Thu 5/23

1 stop8h 35m

$509

George Town Owen Roberts IntlChicago O'Hare Intl

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 8/2

1 stop8h 51m

Chicago O'Hare Intl

Mon 8/5

1 stop5h 30m

$569

George Town Owen Roberts IntlChicago O'Hare Intl

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 5/31

1 stop7h 05m

Chicago O'Hare Intl

Fri 6/7

1 stop6h 35m

$648

George Town Owen Roberts IntlChicago O'Hare Intl

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 5/31

2 stops11h 44m

Chicago O'Hare Intl

Fri 6/7

2 stops7h 35m

$690

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 Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated May 6, 2024.
To help decide which airline to fly from Cayman Islands to Chicago, see what other customers have to say about Air Canada, Delta and United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.1
Very good
10,818 reviews
Check prices

Boarding

8.2

Comfort

7.9

Crew

8.6

Entertainment

8.0

Overall

8.1

Food

7.4

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

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

Boarding

8.2

Comfort

7.9

Crew

8.6

Entertainment

8.0

Overall

8.1

Food

7.4

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

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

Boarding

8.2

Comfort

7.9

Crew

8.6

Entertainment

8.0

Overall

8.1

Food

7.4

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

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

Boarding

8.2

Comfort

7.9

Crew

8.6

Entertainment

8.0

Overall

8.1

Food

7.4

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

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

Boarding

8.2

Comfort

7.9

Crew

8.6

Entertainment

8.0

Overall

8.1

Food

7.4

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Related info for your journey

Find useful and relevant information for your journey from Cayman Islands to Chicago. 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 Cayman Islands to Chicago for under $500 on Cheapflights?

    Yes, there are multiple flights from Cayman Islands to Chicago for under $500. The cheapest flight booked recently is on Multiple Airlines for just $418, but on average you can expect to pay $542.

  • Are there nonstop flights from Cayman Islands to Chicago for under $700 on Cheapflights?

    Cheapflights has at least 1 direct flight from Cayman Islands to Chicago under $700. A good price for a nonstop flight from Cayman Islands to Chicago is less than $694.

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

    On average you can expect to pay $485 for a flight from Cayman Islands to Chicago. The cheapest flight overall is $263 while the most popular route, (George Town Owen Roberts Intl - Chicago O'Hare Intl) is currently priced at $418.

  • What does GCM to ORD mean?

    GCM stands for George Town Owen Roberts Intl Airport, while ORD stands for Chicago O'Hare Intl Airport. These codes are often called IATA codes, a set of identifiers established by IATA (International Air Transport Association) that is widely used by airlines and the aviation industry. While you’re still figuring out your travel plans, it’s not a bad idea to learn the names and codes of other airports around these areas: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

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

    The amount of baggage you can bring on your Cayman Islands to Chicago 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 Cayman Islands to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Cayman Islands to Chicago 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 Cayman Islands to Chicago that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Cayman Islands to Chicago 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 Cayman Islands to Chicago that allow pets onboard?

    Many airlines flying from Cayman Islands to Chicago 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 Cayman Islands to Chicago?

    Yes, you can often find last-minute deals on Cayman Islands to Chicago 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 Cayman Islands to Chicago flight deals updated?

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

See more FAQs

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

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Top 2 airlines flying from Cayman Islands to Chicago

Discover the top 2 airlines that operate flights from Cayman Islands to Chicago. 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 2,719,943 searches. Data last updated May 6, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$397Average$599FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
United AirlinesCheapest$465Average$521FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
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Search flights from Cayman Islands to Chicago by cabin class

Find flights from Cayman Islands to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Classfrom $263/person

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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 Cayman Islands to Chicago?

When you search for this flight from Cayman Islands to Chicago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

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

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Cayman Islands to Chicago for you. Better yet — we are completely free to use.

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

Yes! Cheapflights helps users easily find flights from Cayman Islands to Chicago with no change fees.

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

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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