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Cheap flights from Chicago to Jamaica from $137

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 8/3. 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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0 bags

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Find the cheapest flights from Chicago to Jamaica

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
6:05 am - 1:25 pm
ORD
-
MBJ
7h 20m
1 stop
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
$338American Airlines
Mon, May 11 - Wed, May 20
American Airlines Logo
8:46 pm - 9:13 am
ORD
-
MBJ
12h 27m
1 stop
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
$342American Airlines
Thu, May 14 - Wed, May 20
American Airlines Logo
5:00 am - 11:24 am
ORD
-
MBJ
6h 24m
1 stop
American Airlines Logo
10:17 am - 5:58 pm
MBJ
-
ORD
7h 41m
1 stop
$344American Airlines
Mon, May 11 - Wed, May 20
United Airlines Logo
6:00 am - 3:10 pm
ORD
-
MBJ
9h 10m
1 stop
United Airlines Logo
4:12 pm - 11:26 pm
MBJ
-
ORD
7h 14m
1 stop
$372United Airlines
Sun, Jun 7 - Wed, Jun 17
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
$372Frontier
Mon, May 11 - Thu, May 14
United Airlines Logo
6:30 am - 3:10 pm
ORD
-
MBJ
8h 40m
1 stop
United Airlines Logo
4:12 pm - 11:26 pm
MBJ
-
ORD
7h 14m
1 stop
$374United Airlines
Tue, Jun 2 - Tue, Jun 9
Frontier Logo
6:00 am - 12:27 pm
MDW
-
MBJ
6h 27m
1 stop
Frontier Logo
1:32 pm - 10:08 pm
MBJ
-
MDW
8h 36m
1 stop
$392Frontier
Tue, Jul 21 - Fri, Jul 24
Copa Airlines Logo
1:20 am - 1:54 pm
ORD
-
KIN
12h 34m
1 stop
Copa Airlines Logo
2:56 pm - 4:00 am
KIN
-
ORD
13h 04m
1 stop
$516Copa Airlines
Tue, Jul 21 - Tue, Jul 28
Delta Logo
6:23 am - 8:00 pm
MDW
-
KIN
13h 37m
1 stop
Delta Logo
9:00 am - 9:09 pm
KIN
-
MDW
12h 09m
1 stop
$576Delta
Tue, May 26 - Tue, Jun 2
Delta Logo
9:49 am - 8:00 pm
ORD
-
KIN
10h 11m
1 stop
Delta Logo
9:00 am - 11:59 pm
KIN
-
ORD
14h 59m
1 stop
$576Delta
Fri, May 29 - Sun, May 31

Delta flights from Chicago to Jamaica

Our best Delta deals on Chicago to Jamaica flight tickets
Delta
May 17
MDW6:23 amChicago Midway
6h 33m
1 stop
MBJ12:56 pmMontego Bay Sangster Intl
May 20
MBJ1:18 pmMontego Bay Sangster Intl
7h 51m
1 stop
MDW9:09 pmChicago Midway
$452
Delta
May 18
ORD7:00 amChicago O'Hare Intl
8h 34m
2 stops
MBJ3:34 pmMontego Bay Sangster Intl
May 21
MBJ1:18 pmMontego Bay Sangster Intl
8h 35m
1 stop
ORD9:53 pmChicago O'Hare Intl
$457
Delta
May 30
MDW6:36 pmChicago Midway
20h 58m
2 stops
MBJ3:34 pmMontego Bay Sangster Intl
Jun 3
MBJ1:18 pmMontego Bay Sangster Intl
7h 51m
1 stop
MDW9:09 pmChicago Midway
$512

Frontier flights from Chicago to Jamaica

Our best Frontier deals on Chicago to Jamaica flight tickets
Frontier
Jul 21
MDW6:00 amChicago Midway
6h 27m
1 stop
MBJ12:27 pmMontego Bay Sangster Intl
Jul 24
MBJ1:32 pmMontego Bay Sangster Intl
8h 36m
1 stop
MDW10:08 pmChicago Midway
$392
Frontier
Jul 18
MDW6:00 amChicago Midway
6h 27m
1 stop
MBJ12:27 pmMontego Bay Sangster Intl
Jul 24
MBJ1:32 pmMontego Bay Sangster Intl
8h 36m
1 stop
MDW10:08 pmChicago Midway
$406
Frontier
Jul 11
MDW12:11 pmChicago Midway
24h 16m
1 stop
MBJ12:27 pmMontego Bay Sangster Intl
Jul 15
MBJ1:32 pmMontego Bay Sangster Intl
8h 36m
1 stop
MDW10:08 pmChicago Midway
$410

momondo Fare Finder

 
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, momondo users made 832,500 searches. Data last updated May 9, 2026.
Use the filters below to find and compare flights from Chicago to Jamaica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 5/11

6:05 am-1:25 pm

1 stop7h 20m

Montego Bay Sangster Intl

Wed 5/20

1:15 pm-5:55 pm

Nonstop4h 40m

$338

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 5/14

8:46 pm-9:13 am

1 stop12h 27m

Montego Bay Sangster Intl

Wed 5/20

1:15 pm-5:55 pm

Nonstop4h 40m

$342

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 5/11

5:00 am-11:24 am

1 stop6h 24m

Montego Bay Sangster Intl

Wed 5/20

10:17 am-5:58 pm

1 stop7h 41m

$344

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 6/7

6:00 am-3:10 pm

1 stop9h 10m

Montego Bay Sangster Intl

Wed 6/17

4:12 pm-11:26 pm

1 stop7h 14m

$372

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 5/11

6:00 am-12:11 pm

1 stop6h 11m

Montego Bay Sangster Intl

Thu 5/14

1:16 pm-10:02 pm

1 stop8h 46m

$372

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 6/2

6:30 am-3:10 pm

1 stop8h 40m

Montego Bay Sangster Intl

Tue 6/9

4:12 pm-11:26 pm

1 stop7h 14m

$374

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 7/21

6:00 am-12:27 pm

1 stop6h 27m

Montego Bay Sangster Intl

Fri 7/24

1:32 pm-10:08 pm

1 stop8h 36m

$392

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Tue 7/21

1:20 am-1:54 pm

1 stop12h 34m

Kingston Norman Manley

Tue 7/28

2:56 pm-4:00 am

1 stop13h 04m

$516

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Tue 5/26

6:23 am-8:00 pm

1 stop13h 37m

Kingston Norman Manley

Tue 6/2

9:00 am-9:09 pm

1 stop12h 09m

$576

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Fri 5/29

9:49 am-8:00 pm

1 stop10h 11m

Kingston Norman Manley

Sun 5/31

9:00 am-11:59 pm

1 stop14h 59m

$576

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 December. Flight prices, which tend to average around $84, 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 December, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $93.

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 $493. 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 $638.

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 from Chicago to Jamaica?

You are more likely to see cheaper flights to Jamaica from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Jamaica for around $539 when searching 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 $473 on momondo.

Can stopping save me money on Chicago to Jamaica flights?

You could potentially save up to 21% 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

$138

Fastest flight time

3h 50m

Direct flights

Every day

Airports in Jamaica

11 airports
The best one-way flight to Jamaica from Chicago in the past 72 hours is $138. The best round-trip flight deal from Chicago to Jamaica found on momondo in the last 72 hours is $418.
The fastest flight from Chicago to Jamaica takes 3h 50m
Direct flights go from Chicago to Jamaica every day.
There are 11 airports in Jamaica. From Chicago there are direct flights to Montego Bay Sangster Intl (MBJ).
Search flight deals

Frequently asked questions about flying from Chicago to Jamaica

  • 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
Spirit AirlinesPriceFrom $100Free CancellationRating
6.3
8,634 reviews
Search Spirit Airlines flights
FrontierPriceFrom $144Free CancellationRating
5.6
2,958 reviews
Search Frontier flights
DeltaPriceFrom $178Free CancellationRating
7.9
8,457 reviews
Search Delta flights
JetBluePriceFrom $297Free CancellationRating
7.1
2,978 reviews
Search JetBlue flights
United AirlinesPriceFrom $302Free CancellationRating
7.4
9,696 reviews
Search United Airlines flights
American AirlinesPriceFrom $319Free CancellationRating
7.1
11,669 reviews
Search American Airlines flights
SouthwestPriceFrom $468Free CancellationRating
8.0
4,303 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.

An easier way to manage your Jamaica trip

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