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Cheap flights from Chicago (CHI) to Jamaica from $99

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 5/14. 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 — MBJ
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 Chicago to Jamaica?

Our data shows that August tends to be the cheapest month to fly to Jamaica from Chicago. Users have commonly found prices around $533 for the month, but tickets can be as low as $239. Due to multiple factors, prepare for potentially higher prices in December.

When is the cheapest time to fly from Chicago to Jamaica (CHI - JM)?

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

Cheap Frontier flights from Chicago to Jamaica

Explore cheap flight options specifically provided by Frontier for the route between Chicago and Jamaica. 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 Frontier flights heading from Chicago to Jamaica. Make sure to check back often as deals are often changing.
Sat 7/66:00 amMDW - MBJ
1 stop24h 57mFrontier
Tue 7/92:35 pmMBJ - MDW
1 stop6h 35mFrontier
Deal found 5/5$286
Thu 9/59:44 pmMDW - MBJ
1 stop9h 13mFrontier
Tue 9/108:07 amMBJ - MDW
1 stop12h 42mFrontier
Deal found 5/5$320
Thu 9/57:59 pmORD - MBJ
1 stop10h 58mFrontier
Tue 9/108:07 amMBJ - ORD
1 stop10h 27mFrontier
Deal found 5/5$326
Mon 5/134:56 pmMDW - MBJ
2 stops38h 24mFrontier
Fri 5/1710:07 amMBJ - MDW
2 stops25h 06mFrontier
Deal found 5/5$347
Sun 5/2612:14 pmMDW - MBJ
1 stop20h 41mFrontier
Sat 6/18:07 amMBJ - MDW
1 stop12h 53mFrontier
Deal found 5/5$362
Thu 9/51:21 pmORD - MBJ
1 stop17h 36mFrontier
Wed 9/118:07 amMBJ - ORD
1 stop25h 01mFrontier
Deal found 5/5$369
Sun 9/87:59 pmORD - MBJ
1 stop10h 58mFrontier
Fri 9/138:07 amMBJ - ORD
1 stop8h 24mFrontier
Deal found 5/5$380
Mon 5/136:00 amORD - MBJ
1 stop25h 20mFrontier
Fri 5/1710:07 amMBJ - ORD
2 stops38h 11mFrontier
Deal found 5/5$384
Sun 6/29:53 pmMDW - MBJ
1 stop11h 02mFrontier
Sat 6/84:49 pmMBJ - MDW
1 stop13h 11mFrontier
Deal found 5/5$386

Cheap Spirit Airlines flights from Chicago to Jamaica

Explore cheap flight options specifically provided by Spirit Airlines for the route between Chicago and Jamaica. 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 Spirit Airlines flights from Chicago to Jamaica. If these deals don't fit your criteria, make sure to check back soon as new deals are always added.
Sun 5/265:00 amORD - MBJ
1 stop6h 41mSpirit Airlines
Sat 6/112:45 pmMBJ - ORD
1 stop10h 44mSpirit Airlines
Deal found 5/5$298
Sat 5/185:00 amORD - MBJ
1 stop6h 41mSpirit Airlines
Wed 5/221:01 pmMBJ - ORD
1 stop10h 51mSpirit Airlines
Deal found 5/5$300
Sat 6/17:12 amORD - MBJ
1 stop28h 29mSpirit Airlines
Wed 6/512:46 pmMBJ - ORD
1 stop28h 54mSpirit Airlines
Deal found 5/5$306
Sun 5/2610:58 amORD - MBJ
2 stops25h 02mSpirit Airlines
Sat 6/13:55 pmMBJ - ORD
2 stops18h 00mSpirit Airlines
Deal found 5/5$311
Sun 6/25:00 amORD - MBJ
1 stop6h 41mSpirit Airlines
Sat 6/812:46 pmMBJ - ORD
1 stop10h 07mSpirit Airlines
Deal found 5/5$315
Fri 6/79:37 pmORD - MBJ
2 stops14h 04mSpirit Airlines
Wed 6/1212:46 pmMBJ - ORD
1 stop10h 07mSpirit Airlines
Deal found 5/5$329
Sat 6/17:12 amORD - MBJ
1 stop28h 29mSpirit Airlines
Wed 6/512:46 pmMBJ - ORD
2 stops25h 43mSpirit Airlines
Deal found 5/5$331
Thu 6/206:40 pmORD - MBJ
1 stop17h 01mSpirit Airlines
Wed 6/2612:46 pmMBJ - ORD
1 stop10h 07mSpirit Airlines
Deal found 5/5$333
Wed 5/295:00 amORD - MBJ
1 stop6h 41mSpirit Airlines
Wed 6/512:46 pmMBJ - ORD
2 stops19h 48mSpirit Airlines
Deal found 5/5$334

Cheap Chicago to Jamaica flights in May & June 2024

Find cheap flight options from Chicago to Jamaica 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.
The lowest fares we've come across on flights traveling from Chicago to Jamaica in May and June 2024. Check back soon for alternative fares.
Sun 5/265:00 amORD - MBJ
1 stop6h 41mSpirit Airlines
Sat 6/112:45 pmMBJ - ORD
1 stop10h 44mSpirit Airlines
Deal found 5/5$298
Sat 5/185:00 amORD - MBJ
1 stop6h 41mSpirit Airlines
Wed 5/221:01 pmMBJ - ORD
1 stop10h 51mSpirit Airlines
Deal found 5/5$300
Sat 6/17:12 amORD - MBJ
1 stop28h 29mSpirit Airlines
Wed 6/512:46 pmMBJ - ORD
1 stop28h 54mSpirit Airlines
Deal found 5/5$306
Sun 5/197:00 amORD - MBJ
1 stop6h 28mMultiple Airlines
Fri 5/3112:45 pmMBJ - ORD
1 stop10h 44mMultiple Airlines
Deal found 5/6$307
Sun 5/2610:58 amORD - MBJ
2 stops25h 02mSpirit Airlines
Sat 6/13:55 pmMBJ - ORD
2 stops18h 00mSpirit Airlines
Deal found 5/5$311
Sun 6/25:00 amORD - MBJ
1 stop6h 41mSpirit Airlines
Sat 6/812:46 pmMBJ - ORD
1 stop10h 07mSpirit Airlines
Deal found 5/5$315
Sat 5/1811:00 amORD - MBJ
1 stop21h 11mMultiple Airlines
Wed 5/223:59 pmMBJ - ORD
2 stops17h 56mMultiple Airlines
Deal found 5/5$317
Tue 5/217:00 amORD - MBJ
1 stop6h 28mMultiple Airlines
Fri 5/2412:45 pmMBJ - ORD
1 stop10h 44mMultiple Airlines
Deal found 5/5$322
Sun 6/29:53 pmMDW - MBJ
1 stop11h 02mMultiple Airlines
Sat 6/812:46 pmMBJ - MDW
2 stops9h 01mMultiple Airlines
Deal found 5/5$327

Chicago to Jamaica 2024 flight deals

Discover exclusive flight deals for travel between Chicago and Jamaica 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.
The lowest fares we've come across on flights traveling from Chicago to Jamaica in May and June 2024. Check back soon for alternative fares.
Sat 7/66:00 amMDW - MBJ
1 stop24h 57mFrontier
Tue 7/92:35 pmMBJ - MDW
1 stop6h 35mFrontier
Deal found 5/5$286
Sun 5/265:00 amORD - MBJ
1 stop6h 41mSpirit Airlines
Sat 6/112:45 pmMBJ - ORD
1 stop10h 44mSpirit Airlines
Deal found 5/5$298
Sat 5/185:00 amORD - MBJ
1 stop6h 41mSpirit Airlines
Wed 5/221:01 pmMBJ - ORD
1 stop10h 51mSpirit Airlines
Deal found 5/5$300
Sat 6/17:12 amORD - MBJ
1 stop28h 29mSpirit Airlines
Wed 6/512:46 pmMBJ - ORD
1 stop28h 54mSpirit Airlines
Deal found 5/5$306
Sun 5/197:00 amORD - MBJ
1 stop6h 28mMultiple Airlines
Fri 5/3112:45 pmMBJ - ORD
1 stop10h 44mMultiple Airlines
Deal found 5/6$307
Sun 5/2610:58 amORD - MBJ
2 stops25h 02mSpirit Airlines
Sat 6/13:55 pmMBJ - ORD
2 stops18h 00mSpirit Airlines
Deal found 5/5$311
Sun 6/25:00 amORD - MBJ
1 stop6h 41mSpirit Airlines
Sat 6/812:46 pmMBJ - ORD
1 stop10h 07mSpirit Airlines
Deal found 5/5$315
Sat 5/1811:00 amORD - MBJ
1 stop21h 11mMultiple Airlines
Wed 5/223:59 pmMBJ - ORD
2 stops17h 56mMultiple Airlines
Deal found 5/5$317
Thu 9/59:44 pmMDW - MBJ
1 stop9h 13mFrontier
Tue 9/108:07 amMBJ - MDW
1 stop12h 42mFrontier
Deal found 5/5$320

Non-stop flights to Jamaica from Chicago

Discover non-stop flight options from Chicago to Jamaica. 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.
To help reduce your travel time, choose from one of these non-stop flights from Chicago to Jamaica. Those looking to potentially save on 1 or 2-stop flights from Chicago to Jamaica should utilize the search form at the the top of the page.
Sun 7/78:45 amORD - MBJ
Nonstop3h 55mAmerican Airlines
Thu 7/112:05 pmMBJ - ORD
Nonstop4h 30mAmerican Airlines
Deal found 5/5$393
Tue 10/158:20 amORD - MBJ
Nonstop3h 56mAmerican Airlines
Tue 10/222:27 pmMBJ - ORD
Nonstop4h 28mAmerican Airlines
Deal found 5/5$395
Mon 7/88:45 amORD - MBJ
Nonstop3h 55mAmerican Airlines
Sun 7/142:05 pmMBJ - ORD
Nonstop4h 30mAmerican Airlines
Deal found 5/5$453
Sun 5/199:10 amORD - MBJ
Nonstop4h 00mAmerican Airlines
Thu 5/232:05 pmMBJ - ORD
Nonstop4h 30mAmerican Airlines
Deal found 5/5$458
Thu 7/48:50 amORD - MBJ
Nonstop4h 05mAmerican Airlines
Mon 7/82:05 pmMBJ - ORD
Nonstop4h 30mAmerican Airlines
Deal found 5/5$496
Sun 5/268:45 amORD - MBJ
Nonstop4h 00mUnited Airlines
Sat 6/11:51 pmMBJ - ORD
Nonstop4h 24mUnited Airlines
Deal found 5/5$503
Wed 10/238:20 amORD - MBJ
Nonstop3h 56mAmerican Airlines
Tue 10/292:28 pmMBJ - ORD
Nonstop4h 27mAmerican Airlines
Deal found 5/5$513
Sun 5/199:10 amORD - MBJ
Nonstop4h 00mAmerican Airlines
Fri 5/312:05 pmMBJ - ORD
Nonstop4h 30mAmerican Airlines
Deal found 5/6$518
Sat 6/228:50 amORD - MBJ
Nonstop4h 05mAmerican Airlines
Thu 6/272:05 pmMBJ - ORD
Nonstop4h 30mAmerican Airlines
Deal found 5/5$538

Chicago to Jamaica flights leaving soon

Find last-minute flight options from Chicago to Jamaica 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 2,719,943 searches. Data last updated May 6, 2024.
Check out these flights departing soon from Chicago to Jamaica. Users should examine the flight details to ensure there are no surprises.
Mon 5/134:56 pmMDW - MBJ
2 stops38h 24mFrontier
Fri 5/1710:07 amMBJ - MDW
2 stops25h 06mFrontier
Deal found 5/5$347
Mon 5/136:00 amORD - MBJ
1 stop25h 20mFrontier
Fri 5/1710:07 amMBJ - ORD
2 stops38h 11mFrontier
Deal found 5/5$384
Mon 5/135:00 amORD - MBJ
1 stop6h 41mSpirit Airlines
Fri 5/1712:45 pmMBJ - ORD
1 stop10h 44mSpirit Airlines
Deal found 5/5$394
Fri 5/106:08 pmMDW - MBJ
1 stop16h 30mFrontier
Tue 5/148:32 amMBJ - MDW
1 stop10h 43mFrontier
Deal found 5/5$410
Mon 5/136:00 amORD - MBJ
1 stop25h 20mMultiple Airlines
Fri 5/171:05 pmMBJ - ORD
1 stop10h 05mMultiple Airlines
Deal found 5/5$412
Mon 5/136:47 pmORD - MBJ
2 stops36h 33mFrontier
Fri 5/1710:07 amMBJ - ORD
2 stops38h 11mFrontier
Deal found 5/5$429
Mon 5/135:00 amORD - MBJ
1 stop6h 41mSpirit Airlines
Fri 5/171:05 pmMBJ - ORD
2 stops27h 30mSpirit Airlines
Deal found 5/5$435
Mon 5/136:55 amMDW - MBJ
1 stop24h 25mFrontier
Fri 5/1710:07 amMBJ - MDW
2 stops25h 06mFrontier
Deal found 5/5$440
Mon 5/1310:58 amORD - MBJ
2 stops49h 02mSpirit Airlines
Fri 5/171:05 pmMBJ - ORD
2 stops28h 35mSpirit Airlines
Deal found 5/5$480

One-way flights to Jamaica from Chicago

Search for one-way flight options from Chicago to Jamaica. 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.
Take a look at some of the one-way flights we've detected from Chicago to Jamaica. Those seeking round-trip flights from Chicago to Jamaica should utilize the search form at the the top of the page.
Tue 5/146:00 amORD - MBJ
1 stop8h 53mFrontier
Deal found 5/5$99
Tue 5/148:16 pmMDW - MBJ
1 stop11h 04mFrontier
Deal found 5/5$99
Mon 6/35:00 amORD - MBJ
1 stop6h 41mSpirit Airlines
Deal found 5/5$100
Mon 6/37:53 amMDW - MBJ
1 stop23h 04mFrontier
Deal found 5/5$122
Sat 5/186:40 pmORD - MBJ
1 stop17h 01mSpirit Airlines
Deal found 5/5$126
Sun 6/26:25 amORD - MBJ
1 stop26h 30mFrontier
Deal found 5/5$134
Sat 5/187:53 amMDW - MBJ
1 stop24h 18mFrontier
Deal found 5/5$135
Thu 6/66:40 pmORD - KIN
1 stop16h 38mSpirit Airlines
Deal found 5/5$137
Sun 6/26:40 pmORD - MBJ
2 stops17h 20mSpirit Airlines
Deal found 5/5$139

Find flights from Chicago to Jamaica within your budget

Customize your flight search to find flights from Chicago to Jamaica 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

$286 - $529

Route

Depart

Return

Price

Chicago MidwayMontego Bay Sangster Intl

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 7/6

1 stop24h 57m

Montego Bay Sangster Intl

Tue 7/9

1 stop6h 35m

$286

Chicago O'Hare IntlMontego Bay Sangster Intl

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 5/26

1 stop6h 41m

Montego Bay Sangster Intl

Sat 6/1

1 stop10h 44m

$298

Chicago O'Hare IntlMontego Bay Sangster Intl

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 5/18

1 stop6h 41m

Montego Bay Sangster Intl

Wed 5/22

1 stop10h 51m

$300

Chicago O'Hare IntlMontego Bay Sangster Intl

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 5/19

1 stop6h 28m

Montego Bay Sangster Intl

Fri 5/31

1 stop10h 44m

$307

Chicago O'Hare IntlMontego Bay Sangster Intl

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 5/18

1 stop21h 11m

Montego Bay Sangster Intl

Wed 5/22

2 stops17h 56m

$317

Chicago O'Hare IntlMontego Bay Sangster Intl

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 7/7

Nonstop3h 55m

Montego Bay Sangster Intl

Thu 7/11

Nonstop4h 30m

$393

Chicago O'Hare IntlMontego Bay Sangster Intl

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 5/19

1 stop7h 25m

Montego Bay Sangster Intl

Fri 5/31

Nonstop4h 24m

$451

Chicago MidwayMontego Bay Sangster Intl

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 7/2

1 stop24h 20m

Montego Bay Sangster Intl

Thu 7/11

1 stop7h 16m

$458

Chicago O'Hare IntlKingston Norman Manley

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Mon 6/3

1 stop24h 55m

Kingston Norman Manley

Wed 6/12

1 stop28h 50m

$529

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 Jamaica

Get insights into the airlines that provide service to Jamaica. 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 Jamaica. Reviews last updated May 6, 2024.
See what other customers who have flown with Frontier, Spirit Airlines and American Airlines from Chicago to Jamaica have to say. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.1
Very good
10,818 reviews
Check prices

Overall

8.1

Comfort

7.9

Crew

8.6

Boarding

8.2

Entertainment

8.0

Food

7.4

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

Overall

8.1

Comfort

7.9

Crew

8.6

Boarding

8.2

Entertainment

8.0

Food

7.4

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.

JetBlue
7.6
Good
4,544 reviews
Delta
8.1
Very good
10,818 reviews
Check prices

Overall

8.1

Comfort

7.9

Crew

8.6

Boarding

8.2

Entertainment

8.0

Food

7.4

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
2,957 reviews
Delta
8.1
Very good
10,818 reviews
Check prices

Overall

8.1

Comfort

7.9

Crew

8.6

Boarding

8.2

Entertainment

8.0

Food

7.4

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

Overall

8.1

Comfort

7.9

Crew

8.6

Boarding

8.2

Entertainment

8.0

Food

7.4

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

Overall

8.1

Comfort

7.9

Crew

8.6

Boarding

8.2

Entertainment

8.0

Food

7.4

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 Jamaica. 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 Jamaica for under $300 on Cheapflights?

    Yes, there are multiple flights from Chicago to Jamaica for under $300. The cheapest flight booked recently is on Frontier for just $286, but on average you can expect to pay $321.

  • Are there nonstop flights from Chicago to Jamaica for under $400 on Cheapflights?

    Cheapflights has at least 20 direct flights from Chicago to Jamaica under $400. A good price for a nonstop flight from Chicago to Jamaica is less than $561.

  • Are there last-minute flights available from Chicago to Jamaica for under $400?

    There are currently 20+ open flights from Chicago to Jamaica within the next 7 days for less than $400.

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

    One-way options have recently been found by users for as low as $99 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $100 and American Airlines from $177 one-way.

  • What are the most popular routes from Chicago to Jamaica?

    The most popular flight routes from Chicago to Jamaica are Chicago O'Hare Intl - Montego Bay Sangster Intl, Chicago Midway - Montego Bay Sangster Intl and Chicago O'Hare Intl - Kingston Norman Manley.

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

    American Airlines, Air Canada and Alaska Airlines are the most popular airlines when flying from Chicago to Jamaica.

  • What are the cheapest flights from Chicago to Jamaica?

    On average you can expect to pay $392 for a flight from Chicago to Jamaica. The cheapest flight overall is $176 while the most popular route, (Chicago O'Hare Intl - Montego Bay Sangster Intl) is currently priced at $272.

  • What does ORD to MBJ mean?

    Chicago O'Hare Intl Airport is ORD and Montego Bay Sangster Intl Airport is MBJ. 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. Kingston Norman Manley Airport (KIN), Ocho Rios Boscobel Airport (OCJ), Negril Airport (NEG) are other airports near this flight route and their unique identifiers/IATA codes.

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

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

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

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

  • How can I find direct flights from Chicago to Jamaica?

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

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

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

    Many airlines flying from Chicago to Jamaica 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 Jamaica?

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

    The Chicago to Jamaica 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 Jamaica
See prices for flight routes from nearby airports that may be better suited for you.

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O'Hare Intl to Christiansted flights
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St. Louis to Nassau flights
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St. Louis to Bridgetown flights
O'Hare Intl to Kingstown flights
O'Hare Intl to St. George's flights
St. Louis to Christiansted flights
O'Hare Intl to Havana flights
St. Louis to Willemstad flights
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O'Hare Intl to Aguadilla flights
St. Louis to Simpson Bay flights
St. Louis to Castries flights
O'Hare Intl to Freeport flights

Top 8 airlines flying from Chicago to Jamaica

Discover the top 8 airlines that operate flights from Chicago to Jamaica. 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
Spirit AirlinesCheapest$185Average$395FlexibilityNo cancel feeOn-time65%
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FrontierCheapest$242Average$292FlexibilityNo cancel feeOn-time62%
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United AirlinesCheapest$252Average$548FlexibilityNo cancel feeOn-time69%
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DeltaCheapest$326Average$594FlexibilityNo cancel feeOn-timeN/A
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American AirlinesCheapest$368Average$816FlexibilityNo cancel feeOn-time71%
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British AirwaysCheapest$434Average$460FlexibilityNo cancel feeOn-time70%
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Air CanadaCheapest$560Average$900FlexibilityNo cancel feeOn-time67%
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Alaska AirlinesCheapest$594Average$741FlexibilityNo cancel feeOn-time75%
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Search flights from Chicago to Jamaica by cabin class

Find flights from Chicago to Jamaica, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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Hourly flight availability from Chicago to Jamaica

Find hourly flight availability from Chicago to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 6, 2024.
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0%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
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Fly with Cheapflights

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How does Cheapflights help users find flights from Chicago to Jamaica?

Cheapflights makes it easy to find Chicago to Jamaica flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

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

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

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

Users can book flights with no change fees policies with our dedicated filters. Book flights from Chicago to Jamaica flexibly with Cheapflights today.

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