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Cheap flights from Chicago to Jamaica from $128

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 1/21. 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 to Jamaica

The cheapest plane tickets to Jamaica found on KAYAK recently.
5:11 am - 12:10 pmORD-MBJ
5h 59m1 stop
1:16 pm - 11:32 pmMBJ-ORD
11h 16m1 stop
$291Spirit Airlines
Find Deal
So, Jan 12 - Mi, Jan 15
5:11 am - 12:10 pmORD-MBJ
5h 59m1 stop
2:41 pm - 10:03 pmMBJ-ORD
8h 22m1 stop
$297Spirit Airlines
Find Deal
Di, Feb 4 - Mi, Feb 12
12:51 pm - 1:10 pmMDW-MBJ
23h 19m1 stop
2:20 pm - 11:29 pmMBJ-MDW
10h 09m1 stop
$330Frontier
Find Deal
Fr, Jan 31 - Sa, Feb 8
8:01 pm - 10:34 amMDW-MBJ
13h 33m1 stop
11:48 am - 9:32 pmMBJ-MDW
10h 44m1 stop
$386Frontier
Find Deal
Mi, Feb 5 - So, Feb 9
7:09 pm - 12:25 pmORD-KIN
16h 16m1 stop
3:15 pm - 11:25 pmKIN-ORD
9h 10m1 stop
$440American Airlines
Find Deal
So, Mrz 2 - Do, Mrz 6
5:10 am - 2:20 pmORD-KIN
8h 10m2 stops
1:45 pm - 11:59 pmKIN-ORD
11h 14m2 stops
$454American Airlines
Find Deal
Fr, Jan 24 - Di, Feb 4
8:41 am - 1:46 pmORD-MBJ
4h 05mnonstop
2:48 pm - 6:10 pmMBJ-ORD
4h 22mnonstop
$465United Airlines
Find Deal
So, Feb 9 - Fr, Feb 14
6:00 am - 2:37 pmORD-MBJ
7h 37m1 stop
2:48 pm - 6:10 pmMBJ-ORD
4h 22mnonstop
$469United Airlines
Find Deal
So, Feb 9 - Fr, Feb 14
10:57 am - 8:52 pmMDW-MBJ
8h 55m1 stop
8:00 am - 4:20 pmMBJ-MDW
9h 20m1 stop
$479Delta
Find Deal
Mo, Feb 17 - Fr, Feb 28
9:34 am - 8:52 pmMDW-MBJ
10h 18m2 stops
8:00 am - 6:14 pmMBJ-MDW
11h 14m2 stops
$484Delta
Find Deal
So, Jan 19 - Fr, Jan 24
5:11 am - 12:10 pmORD-MBJ
5h 59m1 stop
$128Spirit Airlines
Find Deal
Di, Jan 21
8:01 pm - 10:34 amMDW-MBJ
13h 33m1 stop
$136Frontier
Find Deal
Mi, Jan 29
8:41 am - 1:46 pmORD-MBJ
4h 05mnonstop
$212United Airlines
Find Deal
Mo, Mrz 3
8:00 am - 12:00 pmMDW-MBJ
4h 00mnonstop
$212Southwest
Find Deal
Di, Mrz 11
8:55 am - 3:10 pmORD-MBJ
6h 15m1 stop
$216United Airlines
Find Deal
Di, Apr 8
9:30 am - 8:35 pmMDW-MBJ
11h 05m2 stops
$216Delta
Find Deal
Di, Mrz 11
8:35 pm - 12:45 pmMDW-MBJ
15h 10m2 stops
$222Southwest
Find Deal
So, Mrz 2
9:13 am - 2:23 pmORD-MBJ
4h 10mnonstop
$237American Airlines
Find Deal
Fr, Jan 31
9:33 am - 8:52 pmMDW-MBJ
10h 19m2 stops
$241Delta
Find Deal
Sa, Mrz 8
8:05 am - 12:10 pmORD-MBJ
4h 05mnonstop
$262American Airlines
Find Deal
So, Apr 13
6:00 am - 5:04 pmORD-MBJ
10h 04m1 stop
3:20 pm - 6:55 pmMBJ-ORD
4h 35mnonstop
$648American Airlines
Find Deal
Mi, Dez 25 - Di, Dez 31
6:00 am - 5:04 pmORD-MBJ
10h 04m1 stop
11:15 am - 7:24 pmMBJ-ORD
9h 09m1 stop
$658American Airlines
Find Deal
Mi, Dez 25 - Di, Dez 31
8:55 pm - 9:09 amORD-KIN
35h 14m2 stops
2:38 pm - 11:32 pmKIN-ORD
9h 54m1 stop
$720Spirit Airlines
Find Deal
Di, Dez 24 - Di, Jan 14
5:11 pm - 9:09 amORD-KIN
14h 58m1 stop
10:14 am - 4:06 pmKIN-ORD
6h 52m1 stop
$849Spirit Airlines
Find Deal
Sa, Dez 21 - Mo, Dez 30
2:40 pm - 8:54 amMDW-MBJ
17h 14m1 stop
10:29 am - 1:24 pmMBJ-MDW
27h 55m1 stop
$861Frontier
Find Deal
So, Dez 22 - Di, Dez 24
8:41 am - 1:46 pmORD-MBJ
4h 05mnonstop
2:48 pm - 6:10 pmMBJ-ORD
4h 22mnonstop
$871United Airlines
Find Deal
Mo, Dez 23 - Di, Dez 31
8:41 am - 1:46 pmORD-MBJ
4h 05mnonstop
2:48 pm - 6:10 pmMBJ-ORD
4h 22mnonstop
$888United Airlines
Find Deal
Mo, Dez 23 - Mi, Dez 25
2:20 pm - 9:09 amMDW-MBJ
17h 49m1 stop
10:29 am - 9:17 pmMBJ-MDW
11h 48m1 stop
$906Frontier
Find Deal
Mo, Dez 23 - Mi, Dez 25
10:30 am - 8:51 pmORD-MBJ
9h 21m2 stops
8:00 am - 9:17 pmMBJ-ORD
14h 17m2 stops
$1,830Delta
Find Deal
Mi, Dez 25 - Di, Dez 31
10:00 am - 8:51 pmORD-MBJ
9h 51m1 stop
3:05 pm - 10:52 pmMBJ-ORD
8h 47m1 stop
$1,896Delta
Find Deal
Di, Dez 24 - So, Dez 29
8:41 am - 1:46 pmORD-MBJ
4h 05mnonstop
2:48 pm - 6:10 pmMBJ-ORD
4h 22mnonstop
$465United Airlines
Find Deal
So, Feb 9 - Fr, Feb 14
8:41 am - 1:46 pmORD-MBJ
4h 05mnonstop
2:48 pm - 6:10 pmMBJ-ORD
4h 22mnonstop
$490United Airlines
Find Deal
Sa, Jan 11 - Mi, Jan 15
8:41 am - 1:46 pmORD-MBJ
4h 05mnonstop
2:48 pm - 6:10 pmMBJ-ORD
4h 22mnonstop
$495United Airlines
Find Deal
Mo, Feb 24 - Fr, Feb 28
8:41 am - 1:46 pmORD-MBJ
4h 05mnonstop
2:48 pm - 6:10 pmMBJ-ORD
4h 22mnonstop
$503United Airlines
Find Deal
Sa, Feb 22 - Mi, Feb 26
9:13 am - 2:23 pmORD-MBJ
4h 10mnonstop
1:15 pm - 4:50 pmMBJ-ORD
4h 35mnonstop
$515American Airlines
Find Deal
Fr, Jan 31 - Sa, Feb 8
9:13 am - 2:23 pmORD-MBJ
4h 10mnonstop
3:37 pm - 7:17 pmMBJ-ORD
4h 40mnonstop
$528American Airlines
Find Deal
Mo, Feb 10 - So, Feb 16
9:13 am - 2:23 pmORD-MBJ
4h 10mnonstop
3:23 pm - 6:58 pmMBJ-ORD
4h 35mnonstop
$529American Airlines
Find Deal
So, Feb 2 - So, Feb 9
8:41 am - 1:46 pmORD-MBJ
4h 05mnonstop
2:48 pm - 6:10 pmMBJ-ORD
4h 22mnonstop
$550Lufthansa
Find Deal
So, Jan 19 - Di, Jan 28
9:05 am - 1:05 pmMDW-MBJ
4h 00mnonstop
1:00 pm - 5:15 pmMBJ-MDW
4h 15mnonstop
$611Southwest
Find Deal
So, Mrz 16 - Do, Mrz 20
8:00 am - 12:00 pmMDW-MBJ
4h 00mnonstop
1:00 pm - 5:15 pmMBJ-MDW
4h 15mnonstop
$651Southwest
Find Deal
Do, Mrz 13 - Do, Mrz 20

Spirit Airlines flights from Chicago to Jamaica

Our best Spirit Airlines deals on Chicago to Jamaica flight tickets
Spirit Airlines
Jan 12
ORD5:11 amChicago O'Hare Intl
5h 59m
1 stop
MBJ12:10 pmMontego Bay Sangster Intl
Jan 15
MBJ1:16 pmMontego Bay Sangster Intl
11h 16m
1 stop
ORD11:32 pmChicago O'Hare Intl
Spirit Airlines
Feb 4
ORD5:11 amChicago O'Hare Intl
5h 59m
1 stop
MBJ12:10 pmMontego Bay Sangster Intl
Feb 12
MBJ2:41 pmMontego Bay Sangster Intl
8h 22m
1 stop
ORD10:03 pmChicago O'Hare Intl
Spirit Airlines
Feb 3
ORD5:11 amChicago O'Hare Intl
5h 59m
1 stop
MBJ12:10 pmMontego Bay Sangster Intl
Feb 10
MBJ1:16 pmMontego Bay Sangster Intl
11h 16m
1 stop
ORD11:32 pmChicago O'Hare Intl

Frontier flights from Chicago to Jamaica

Our best Frontier deals on Chicago to Jamaica flight tickets
Frontier
Jan 31
MDW12:51 pmChicago Midway
23h 19m
1 stop
MBJ1:10 pmMontego Bay Sangster Intl
Feb 8
MBJ2:20 pmMontego Bay Sangster Intl
10h 09m
1 stop
MDW11:29 pmChicago Midway
Frontier
Feb 5
MDW8:01 pmChicago Midway
13h 33m
1 stop
MBJ10:34 amMontego Bay Sangster Intl
Feb 9
MBJ11:48 amMontego Bay Sangster Intl
10h 44m
1 stop
MDW9:32 pmChicago Midway
Frontier
Feb 5
MDW8:01 pmChicago Midway
13h 33m
1 stop
MBJ10:34 amMontego Bay Sangster Intl
Feb 9
MBJ11:48 amMontego Bay Sangster Intl
23h 40m
2 stops
MDW10:28 amChicago Midway

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 January. Flight prices, which tend to average around $471, 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 January, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $473.

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?

Most flyers found that booking tickets 40 days in advance of their planned departure date is the best time to get cheap flights to Jamaica. During this timeframe, flight prices are around $565. However, in the past 72 hours, people saw flights from Chicago for as low as $368.

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.

Can stopping save me money on Chicago to Jamaica flights?

You could potentially save up to 39% on your flight if you consider stops on a Chicago to Jamaica flight.

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

$128

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 $128. The best round-trip flight deal from Chicago to Jamaica found on momondo in the last 72 hours is $291.
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
6.1
3,475 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $267Free CancellationRating
6.3
8,120 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $368Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $368Free CancellationRating
8.0
8,601 reviews
Search Delta flights
United AirlinesPriceFrom $393Free CancellationRating
7.4
9,043 reviews
Search United Airlines flights
SouthwestPriceFrom $579Free CancellationRating
8.1
4,821 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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