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Cheap flights from the Cayman Islands to Chicago (CHI) from $409

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/2. 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 21 — May 281
From?
To?
Tue 5/21
Tue 5/28
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 $586 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 80% 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 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 2,637,452 searches. Data last updated May 16, 2024.
Take a look at some of the lowest-priced Delta flights heading from Cayman Islands to Chicago. Make sure to check back often as deals are often changing.
Fri 8/212:50 pmGCM - ORD
1 stop8h 22mDelta
Mon 8/56:00 amORD - GCM
1 stop5h 30mDelta
Deal found 5/16$409
Fri 8/212:50 pmGCM - MDW
2 stops19h 48mDelta
Mon 8/56:00 amMDW - GCM
1 stop5h 30mDelta
Deal found 5/16$614
Fri 8/212:50 pmGCM - MDW
2 stops19h 48mDelta
Mon 8/56:00 amMDW - GCM
1 stop5h 30mDelta
Deal found 5/15$674
Fri 5/2412:51 pmGCM - ORD
1 stop27h 56mDelta
Tue 5/285:40 amORD - GCM
1 stop5h 46mDelta
Deal found 5/15$764
Fri 5/2412:51 pmGCM - ORD
1 stop19h 26mDelta
Tue 5/287:12 pmORD - GCM
2 stops16h 14mDelta
Deal found 5/15$775
Fri 5/2412:51 pmGCM - ORD
2 stops27h 42mDelta
Tue 5/287:12 pmORD - GCM
2 stops16h 14mDelta
Deal found 5/15$782
Thu 5/2312:51 pmGCM - MDW
1 stop9h 10mDelta
Sun 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/15$783
Thu 5/2312:51 pmGCM - MDW
2 stops28h 15mDelta
Sun 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/15$796
Thu 5/2312:51 pmGCM - MDW
1 stop9h 10mDelta
Sun 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/14$848

Cheap American Airlines flights from Cayman Islands to Chicago

Explore cheap flight options specifically provided by American Airlines 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 2,637,452 searches. Data last updated May 16, 2024.
Take a gander at the lowest prices we've found on American Airlines flights from Cayman Islands to Chicago. Deals are refreshing constantly so come back soon for more options.
Fri 8/212:15 pmGCM - ORD
2 stops20h 42mAmerican Airlines
Mon 8/59:45 amORD - GCM
2 stops27h 20mAmerican Airlines
Deal found 5/15$510
Fri 8/23:35 pmGCM - ORD
1 stop28h 49mAmerican Airlines
Mon 8/57:00 amORD - GCM
1 stop28h 45mAmerican Airlines
Deal found 5/15$526
Fri 5/242:30 pmGCM - ORD
1 stop6h 59mAmerican Airlines
Tue 5/286:27 pmORD - GCM
2 stops18h 38mAmerican Airlines
Deal found 5/14$810

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 2,637,452 searches. Prices were last updated on May 16, 2024.
These are some of the most attractive deals on flights from Cayman Islands to Chicago in 2024. Check back soon for alternative fares.
Fri 5/2412:51 pmGCM - ORD
1 stop27h 56mDelta
Tue 5/285:40 amORD - GCM
1 stop5h 46mDelta
Deal found 5/15$764
Fri 5/2412:51 pmGCM - ORD
1 stop19h 26mDelta
Tue 5/287:12 pmORD - GCM
2 stops16h 14mDelta
Deal found 5/15$775
Fri 5/2412:51 pmGCM - ORD
2 stops27h 42mDelta
Tue 5/287:12 pmORD - GCM
2 stops16h 14mDelta
Deal found 5/15$782
Thu 5/2312:51 pmGCM - MDW
1 stop9h 10mDelta
Sun 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/15$783
Thu 5/2312:51 pmGCM - MDW
2 stops28h 15mDelta
Sun 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/15$796
Fri 5/241:40 pmGCM - ORD
1 stop9h 19mUnited Airlines
Tue 5/289:31 pmORD - GCM
1 stop15h 04mUnited Airlines
Deal found 5/14$803
Fri 5/242:30 pmGCM - ORD
1 stop6h 59mAmerican Airlines
Tue 5/286:27 pmORD - GCM
2 stops18h 38mAmerican Airlines
Deal found 5/14$810
Thu 5/2312:51 pmGCM - MDW
1 stop9h 10mDelta
Sun 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/14$848
Thu 5/2312:51 pmGCM - MDW
2 stops28h 15mDelta
Sun 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/14$861

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 2,637,452 searches. Data last updated May 16, 2024.
These are some of the most attractive deals on flights from Cayman Islands to Chicago in 2024. Check back soon for alternative fares.
Fri 8/212:50 pmGCM - ORD
1 stop8h 22mDelta
Mon 8/56:00 amORD - GCM
1 stop5h 30mDelta
Deal found 5/16$409
Fri 8/212:15 pmGCM - ORD
2 stops20h 42mAmerican Airlines
Mon 8/59:45 amORD - GCM
2 stops27h 20mAmerican Airlines
Deal found 5/15$510
Fri 8/23:35 pmGCM - ORD
1 stop28h 49mAmerican Airlines
Mon 8/57:00 amORD - GCM
1 stop28h 45mAmerican Airlines
Deal found 5/15$526
Fri 8/212:50 pmGCM - MDW
2 stops19h 48mDelta
Mon 8/56:00 amMDW - GCM
1 stop5h 30mDelta
Deal found 5/16$614
Fri 8/212:50 pmGCM - MDW
2 stops19h 48mDelta
Mon 8/56:00 amMDW - GCM
1 stop5h 30mDelta
Deal found 5/15$674
Fri 5/2412:51 pmGCM - ORD
1 stop27h 56mDelta
Tue 5/285:40 amORD - GCM
1 stop5h 46mDelta
Deal found 5/15$764
Fri 5/2412:51 pmGCM - ORD
1 stop19h 26mDelta
Tue 5/287:12 pmORD - GCM
2 stops16h 14mDelta
Deal found 5/15$775
Fri 5/2412:51 pmGCM - ORD
2 stops27h 42mDelta
Tue 5/287:12 pmORD - GCM
2 stops16h 14mDelta
Deal found 5/15$782
Thu 5/2312:51 pmGCM - MDW
1 stop9h 10mDelta
Sun 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/15$783

Cayman Islands to Chicago flights leaving soon

Find last-minute flight options from Cayman Islands to Chicago 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 2,637,452 searches. Data last updated May 16, 2024.
Users seeking a last-minute flight from Cayman Islands to Chicago should consider booking one of these fares. It's wise to confirm all flight details are correct before booking.
Fri 5/2412:51 pmGCM - ORD
1 stop27h 56mDelta
Tue 5/285:40 amORD - GCM
1 stop5h 46mDelta
Deal found 5/15$764
Fri 5/2412:51 pmGCM - ORD
1 stop19h 26mDelta
Tue 5/287:12 pmORD - GCM
2 stops16h 14mDelta
Deal found 5/15$775
Fri 5/2412:51 pmGCM - ORD
2 stops27h 42mDelta
Tue 5/287:12 pmORD - GCM
2 stops16h 14mDelta
Deal found 5/15$782
Thu 5/2312:51 pmGCM - MDW
1 stop9h 10mDelta
Sun 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/15$783
Thu 5/2312:51 pmGCM - MDW
2 stops28h 15mDelta
Sun 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/15$796
Fri 5/241:40 pmGCM - ORD
1 stop9h 19mUnited Airlines
Tue 5/289:31 pmORD - GCM
1 stop15h 04mUnited Airlines
Deal found 5/14$803
Fri 5/242:30 pmGCM - ORD
1 stop6h 59mAmerican Airlines
Tue 5/286:27 pmORD - GCM
2 stops18h 38mAmerican Airlines
Deal found 5/14$810
Thu 5/2312:51 pmGCM - MDW
1 stop9h 10mDelta
Sun 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/14$848
Thu 5/2312:51 pmGCM - MDW
2 stops28h 15mDelta
Sun 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/14$861

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 2,637,452 searches. Data last updated May 16, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$409 - $674

Route

Depart

Return

Price

George Town Owen Roberts IntlChicago O'Hare Intl

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 8/2

1 stop8h 22m

Chicago O'Hare Intl

Mon 8/5

1 stop5h 30m

$409

George Town Owen Roberts IntlChicago O'Hare Intl

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 8/2

2 stops20h 42m

Chicago O'Hare Intl

Mon 8/5

2 stops27h 20m

$510

George Town Owen Roberts IntlChicago O'Hare Intl

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 8/2

1 stop28h 49m

Chicago O'Hare Intl

Mon 8/5

1 stop28h 45m

$526

George Town Owen Roberts IntlChicago Midway

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 8/2

2 stops19h 48m

Chicago Midway

Mon 8/5

1 stop5h 30m

$614

George Town Owen Roberts IntlChicago Midway

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 8/2

2 stops19h 48m

Chicago Midway

Mon 8/5

1 stop5h 30m

$674

Flights are sorted by cheapest first

Deals found on 5/16

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 16, 2024.
To help decide which airline to fly from Cayman Islands to Chicago, see what other customers have to say about Delta and American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
10,673 reviews
Check prices

Overall

8.0

Comfort

7.9

Entertainment

8.0

Food

7.4

Crew

8.6

Boarding

8.2

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
8.0
Very good
10,673 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Overall

8.0

Comfort

7.9

Entertainment

8.0

Food

7.4

Crew

8.6

Boarding

8.2

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
14,514 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Overall

8.0

Comfort

7.9

Entertainment

8.0

Food

7.4

Crew

8.6

Boarding

8.2

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 Delta for just $409, but on average you can expect to pay $546.

  • Are there last-minute flights available from Cayman Islands to Chicago for under $800?

    There are currently 11+ open flights from Cayman Islands to Chicago within the next 7 days for less than $800.

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

    On average you can expect to pay $483 for a flight from Cayman Islands to Chicago. The cheapest flight overall is $286 while the most popular route, (George Town Owen Roberts Intl - Chicago Midway) is currently priced at $559.

  • 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 5/16.

See more FAQs

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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 2,637,452 searches. Data last updated May 16, 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 $286/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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