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Cheap flights from Chicago to Jamaica from $100

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Jamaica departing on 3/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago to Jamaica

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Jamaica that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Jamaica.

Cheap last minute flights

Planning a quick getaway from Chicago to Jamaica? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Jamaica, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Jamaica

Find recent round-trip train or bus tickets from Chicago to Jamaica.

All round-trip flight deals from Chicago to Jamaica

The cheapest plane tickets from Chicago to Jamaica found on KAYAK recently.
5:11 am - 12:10 pmORD-MBJ
5h 59m1 stop
2:48 pm - 11:58 pmMBJ-ORD
10h 10m1 stop
$247Spirit Airlines
Find Deal
Mon, Feb 10 - Wed, Feb 12
5:11 am - 12:10 pmORD-MBJ
5h 59m1 stop
2:48 pm - 11:58 pmMBJ-ORD
10h 10m1 stop
$260Spirit Airlines
Find Deal
Sun, Feb 9 - Wed, Feb 12
6:48 pm - 2:53 pmMDW-MBJ
19h 05m1 stop
1:51 pm - 9:56 pmMBJ-MDW
9h 05m1 stop
$342Frontier
Find Deal
Fri, Feb 28 - Sat, Mar 8
7:30 am - 10:38 amMDW-MBJ
26h 08m1 stop
11:44 am - 6:26 pmMBJ-MDW
7h 42m1 stop
$403Frontier
Find Deal
Sat, Feb 1 - Thu, Feb 6
6:00 am - 12:47 pmMDW-MBJ
5h 47m1 stop
8:00 am - 4:20 pmMBJ-MDW
9h 20m1 stop
$491Delta
Find Deal
Sun, Feb 23 - Thu, Mar 6
9:33 am - 8:52 pmMDW-MBJ
10h 19m2 stops
8:00 am - 6:11 pmMBJ-MDW
11h 11m2 stops
$495Delta
Find Deal
Tue, Feb 25 - Tue, Mar 4
8:25 am - 1:20 pmMDW-MBJ
3h 55mnonstop
3:10 pm - 10:00 pmMBJ-MDW
7h 50m1 stop
$531Southwest
Find Deal
Sat, Feb 1 - Thu, Feb 6
6:35 am - 2:50 pmMDW-MBJ
7h 15m1 stop
1:45 pm - 10:00 pmMBJ-MDW
9h 15m2 stops
$558Southwest
Find Deal
Sat, Feb 1 - Thu, Feb 6
10:15 am - 10:24 pmORD-KIN
11h 09m2 stops
1:28 pm - 10:19 pmKIN-ORD
9h 51m2 stops
$651American Airlines
Find Deal
Sat, Mar 1 - Sat, Mar 8
6:58 pm - 11:24 amORD-KIN
16h 26m1 stop
5:00 am - 9:30 pmKIN-ORD
16h 30m1 stop
$676American Airlines
Find Deal
Sat, Mar 15 - Sat, Mar 22
5:10 am - 11:02 amORD-MBJ
5h 52m1 stop
$100Spirit Airlines
Find Deal
Wed, Mar 12
5:00 am - 1:43 pmORD-MBJ
7h 43m1 stop
$117Spirit Airlines
Find Deal
Tue, Feb 18
8:45 am - 12:49 pmORD-MBJ
4h 04mnonstop
$217United Airlines
Find Deal
Mon, Mar 31
10:25 am - 8:44 pmORD-MBJ
10h 19m2 stops
$222Delta
Find Deal
Wed, Mar 12
9:33 am - 8:52 pmMDW-MBJ
10h 19m2 stops
$222Delta
Find Deal
Wed, Feb 19
8:41 am - 1:46 pmORD-MBJ
4h 05mnonstop
$242United Airlines
Find Deal
Fri, Feb 28
9:40 am - 1:40 pmMDW-MBJ
4h 00mnonstop
$255Southwest
Find Deal
Sat, May 10
7:10 pm - 12:45 pmORD-MBJ
16h 35m2 stops
$260Southwest
Find Deal
Thu, Mar 6
9:00 am - 1:00 pmORD-MBJ
4h 00mnonstop
$267American Airlines
Find Deal
Sun, Apr 13
9:25 am - 1:30 pmORD-MBJ
4h 05mnonstop
$272American Airlines
Find Deal
Thu, Apr 3
5:11 am - 12:10 pmORD-MBJ
5h 59m1 stop
1:16 pm - 8:13 pmMBJ-ORD
7h 57m1 stop
$326Spirit Airlines
Find Deal
Tue, Jan 21 - Tue, Jan 28
5:11 am - 12:10 pmORD-MBJ
5h 59m1 stop
1:16 pm - 12:39 pmMBJ-ORD
24h 23m3 stops
$391Spirit Airlines
Find Deal
Tue, Jan 21 - Tue, Jan 28
9:13 am - 2:23 pmORD-MBJ
4h 10mnonstop
3:18 pm - 6:48 pmMBJ-ORD
4h 30mnonstop
$526American Airlines
Find Deal
Mon, Jan 20 - Sat, Jan 25
8:25 pm - 12:40 pmORD-MBJ
15h 15m1 stop
1:15 pm - 4:50 pmMBJ-ORD
4h 35mnonstop
$531American Airlines
Find Deal
Mon, Jan 20 - Sat, Jan 25
8:41 am - 1:46 pmORD-MBJ
4h 05mnonstop
3:55 pm - 10:57 pmMBJ-ORD
8h 02m1 stop
$536United Airlines
Find Deal
Mon, Jan 20 - Fri, Jan 24
6:00 am - 2:37 pmORD-MBJ
7h 37m1 stop
3:55 pm - 10:57 pmMBJ-ORD
8h 02m1 stop
$541United Airlines
Find Deal
Mon, Jan 20 - Fri, Jan 24
6:15 am - 2:40 pmORD-MBJ
7h 25m1 stop
12:36 pm - 9:15 pmMBJ-ORD
9h 39m2 stops
$545Delta
Find Deal
Mon, Jan 20 - Wed, Jan 29
5:35 am - 12:45 pmMDW-MBJ
6h 10m1 stop
2:10 pm - 5:25 pmMBJ-MDW
4h 15mnonstop
$576Southwest
Find Deal
Sun, Jan 19 - Sat, Jan 25
5:40 am - 12:45 pmMDW-MBJ
6h 05m1 stop
2:10 pm - 5:25 pmMBJ-MDW
4h 15mnonstop
$589Southwest
Find Deal
Mon, Jan 20 - Sat, Jan 25
6:15 am - 2:40 pmORD-MBJ
7h 25m1 stop
12:36 pm - 8:53 pmMBJ-ORD
9h 17m2 stops
$603Delta
Find Deal
Fri, Jan 17 - Fri, Jan 24
9:25 am - 1:30 pmORD-MBJ
4h 05mnonstop
2:30 pm - 7:00 pmMBJ-ORD
4h 30mnonstop
$466American Airlines
Find Deal
Sun, Mar 9 - Thu, Mar 13
8:41 am - 1:46 pmORD-MBJ
4h 05mnonstop
1:48 pm - 6:10 pmMBJ-ORD
4h 22mnonstop
$476United Airlines
Find Deal
Mon, Mar 3 - Mon, Mar 10
8:05 am - 12:05 pmORD-MBJ
4h 00mnonstop
2:20 pm - 6:50 pmMBJ-ORD
4h 30mnonstop
$491American Airlines
Find Deal
Fri, May 9 - Thu, May 15
9:25 am - 1:30 pmORD-MBJ
4h 05mnonstop
2:15 pm - 6:50 pmMBJ-ORD
4h 35mnonstop
$496American Airlines
Find Deal
Tue, Apr 1 - Tue, Apr 8
8:41 am - 1:46 pmORD-MBJ
4h 05mnonstop
2:48 pm - 6:10 pmMBJ-ORD
4h 22mnonstop
$501United Airlines
Find Deal
Sat, Feb 1 - Thu, Feb 6
8:41 am - 1:46 pmORD-MBJ
4h 05mnonstop
2:48 pm - 6:10 pmMBJ-ORD
4h 22mnonstop
$516United Airlines
Find Deal
Fri, Mar 7 - Sat, Mar 8
9:00 am - 1:00 pmORD-MBJ
4h 00mnonstop
2:15 pm - 6:50 pmMBJ-ORD
4h 35mnonstop
$521American Airlines
Find Deal
Fri, Apr 11 - Tue, Apr 15
9:30 am - 2:35 pmORD-MBJ
4h 05mnonstop
2:30 pm - 7:00 pmMBJ-ORD
4h 30mnonstop
$586British Airways
Find Deal
Sun, Mar 2 - Sun, Mar 9
9:30 am - 2:30 pmMDW-MBJ
4h 00mnonstop
3:25 pm - 7:40 pmMBJ-MDW
4h 15mnonstop
$639Southwest
Find Deal
Sat, Mar 8 - Sat, Mar 15
9:40 am - 1:40 pmMDW-MBJ
4h 00mnonstop
2:40 pm - 6:55 pmMBJ-MDW
4h 15mnonstop
$652Southwest
Find Deal
Sat, May 17 - Sat, May 24

Spirit Airlines flights from Chicago to Jamaica

Our best Spirit Airlines deals on Chicago to Jamaica flight tickets
Spirit Airlines
Feb 10
ORD5:11 amChicago O'Hare Intl
5h 59m
1 stop
MBJ12:10 pmMontego Bay Sangster Intl
Feb 12
MBJ2:48 pmMontego Bay Sangster Intl
10h 10m
1 stop
ORD11:58 pmChicago O'Hare Intl
Spirit Airlines
Feb 9
ORD5:11 amChicago O'Hare Intl
5h 59m
1 stop
MBJ12:10 pmMontego Bay Sangster Intl
Feb 12
MBJ2:48 pmMontego Bay Sangster Intl
10h 10m
1 stop
ORD11:58 pmChicago O'Hare Intl
Spirit Airlines
Feb 9
ORD5:11 amChicago O'Hare Intl
5h 59m
1 stop
MBJ12:10 pmMontego Bay Sangster Intl
Feb 12
MBJ2:48 pmMontego Bay Sangster Intl
10h 10m
1 stop
ORD11:58 pmChicago O'Hare Intl

United Airlines flights from Chicago to Jamaica

Our best United Airlines deals on Chicago to Jamaica flight tickets
United Airlines
Jan 23
ORD8:41 amChicago O'Hare Intl
4h 05m
MBJ1:46 pmMontego Bay Sangster Intl
Jan 29
MBJ1:25 pmMontego Bay Sangster Intl
9h 18m
1 stop
ORD9:43 pmChicago O'Hare Intl
United Airlines
Jan 26
ORD8:41 amChicago O'Hare Intl
4h 05m
MBJ1:46 pmMontego Bay Sangster Intl
Jan 30
MBJ2:48 pmMontego Bay Sangster Intl
4h 22m
ORD6:10 pmChicago O'Hare Intl
United Airlines
Jan 25
ORD8:41 amChicago O'Hare Intl
4h 05m
MBJ1:46 pmMontego Bay Sangster Intl
Jan 28
MBJ3:55 pmMontego Bay Sangster Intl
8h 02m
1 stop
ORD10:57 pmChicago O'Hare Intl

See travel insights to Jamaica from

How to get the cheapest flight ticket from Chicago to Jamaica

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Jamaica?

The cheapest month to fly to Jamaica from Chicago is in May. Flight prices, which tend to average around $473, are often lower during this time because this is during the off-season. If you aren’t able to travel to Jamaica during the month of May, then flying in April is also cheap. Prices for this month can be found on momondo for an average of $483.

What is the cheapest day to depart on your flight to Jamaica?

The cheapest day to depart on your flight to Jamaica is on a Tuesday when prices can be found for as low as $507. This is often the case because there is less demand to fly during this day of the week. On the other hand, Thursday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $625.

What is the cheapest time of day to depart on your flight to Jamaica?

Our most recent data shows that the best time of day to fly to Jamaica is at noon. Flights from Chicago to Jamaica during this time can be as low as $287. In the afternoon is when there is more demand to fly to Jamaica, so prices are often more expensive at around $563 per ticket.

What is the cheapest Chicago to Jamaica flight route?

Fly from Chicago O'Hare Intl to Montego Bay Sangster Intl for the best Chicago - Jamaica flight prices

How far in advance should I book a flight to Jamaica?

You are more likely to see cheaper flights to Jamaica from Chicago when booking 16 weeks ahead of your departure date. In general, you can expect to find flights to Jamaica for around $569 when searching 16 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Jamaica from Chicago for as low as $513 on momondo.

What cabin class options are available on Chicago to Jamaica flights?

There are 3 cabin classes available to choose from on Chicago to Jamaica flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap Chicago to Jamaica flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Jamaica

Best Price Found

$100

Fastest flight time

3h 55m

Direct flights

Every day

Airports in Jamaica

2 airports
The best one-way flight to Jamaica from Chicago in the past 72 hours is $100. The best round-trip flight deal from Chicago to Jamaica found on momondo in the last 72 hours is $247.
The fastest flight from Chicago to Jamaica takes 3h 55m
Direct flights go from Chicago to Jamaica every day.
There are 2 airports near Jamaica: Kingston Norman Manley (KIN), Montego Bay Sangster Intl (MBJ)

  • When did momondo last update prices for flights from Chicago to Jamaica?

    Prices for flights from Chicago to Jamaica refresh daily.

  • How many operators does momondo search for flights from Chicago to Jamaica?

  • How old do you have to be to fly from Chicago to Jamaica?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Jamaica.

  • What documentation or ID do you need to fly to Jamaica?

    The necessary travel and health documents for your Jamaica trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago to Jamaica?


Best airlines flying from Chicago to Jamaica

Compare and see reviews for airlines that fly from Chicago to Jamaica with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $65Free CancellationRating
6.0
3,435 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $276Free CancellationRating
6.3
8,098 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $368Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $368Free CancellationRating
8.0
8,511 reviews
Search Delta flights
United AirlinesPriceFrom $385Free CancellationRating
7.4
8,965 reviews
Search United Airlines flights
SouthwestPriceFrom $579Free CancellationRating
8.1
4,659 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Jamaica?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Jamaica. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Jamaica with flexible booking policies on momondo?

Flights from Chicago to Jamaica with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Jamaica?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Jamaica.

I’m not ready to book a flight from Chicago to Jamaica right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Jamaica from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.


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