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Cheap flights from Illinois 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 Illinois 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 Illinois to Jamaica

Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
7:00 am - 5:33 pm
ORD
-
MBJ
10h 33m
1 stop
JetBlue Logo
12:55 pm - 11:44 pm
MBJ
-
ORD
10h 49m
1 stop
$324JetBlue
Tue, Aug 25 - Thu, Aug 27
JetBlue Logo
7:00 am - 5:33 pm
ORD
-
MBJ
10h 33m
1 stop
JetBlue Logo
12:55 pm - 11:44 pm
MBJ
-
ORD
10h 49m
1 stop
$330JetBlue
Sun, Aug 9 - Thu, Aug 27
American Airlines Logo
9:45 am - 3:01 pm
ORD
-
MBJ
4h 16mnonstop
American Airlines Logo
3:14 pm - 6:55 pm
MBJ
-
ORD
4h 41mnonstop
$338American Airlines
Tue, Nov 3 - Tue, Nov 10
American Airlines Logo
5:00 am - 12:54 pm
ORD
-
MBJ
6h 54m
1 stop
American Airlines Logo
2:19 pm - 6:00 pm
MBJ
-
ORD
4h 41mnonstop
$342American Airlines
Tue, Nov 3 - Tue, Nov 10
Frontier Logo
6:00 am - 12:21 pm
MDW
-
MBJ
6h 21m
1 stop
Frontier Logo
1:26 pm - 10:11 pm
MBJ
-
MDW
8h 45m
1 stop
$372Frontier
Wed, Aug 19 - Tue, Aug 25
Frontier Logo
12:27 pm - 12:21 pm
MDW
-
MBJ
23h 54m
1 stop
Frontier Logo
1:26 pm - 10:11 pm
MBJ
-
MDW
8h 45m
1 stop
$390Frontier
Tue, Aug 18 - Tue, Aug 25
United Airlines Logo
2:29 pm - 11:43 am
MLI
-
MBJ
21h 14m
2 stops
United Airlines Logo
12:52 pm - 10:14 am
MBJ
-
MLI
21h 22m
2 stops
$487United Airlines
Mon, Sep 21 - Thu, Sep 24
United Airlines Logo
6:30 pm - 3:10 pm
MLI
-
MBJ
20h 40m
2 stops
United Airlines Logo
4:33 pm - 11:16 pm
MBJ
-
MLI
30h 43m
2 stops
$497United Airlines
Mon, Jun 8 - Sun, Jun 14
Multiple Airlines Logo
2:35 pm - 9:20 pm
ORD
-
KIN
6h 45m
1 stop
Multiple Airlines Logo
3:05 pm - 9:00 am
KIN
-
ORD
17h 55m
1 stop
$511Multiple Airlines
Wed, Jul 22 - Tue, Jul 28
Multiple Airlines Logo
3:40 pm - 1:55 pm
ORD
-
KIN
46h 15m
2 stops
Multiple Airlines Logo
4:05 pm - 11:44 pm
KIN
-
ORD
7h 39m
1 stop
$530Multiple Airlines
Sat, Sep 19 - Sat, Sep 26

JetBlue flights from Illinois to Jamaica

Our best JetBlue deals on Illinois to Jamaica flight tickets
JetBlue
Aug 25
ORD7:00 amChicago O'Hare Intl
10h 33m
1 stop
MBJ5:33 pmMontego Bay Sangster Intl
Aug 27
MBJ12:55 pmMontego Bay Sangster Intl
10h 49m
1 stop
ORD11:44 pmChicago O'Hare Intl
$324
JetBlue
Aug 9
ORD7:00 amChicago O'Hare Intl
10h 33m
1 stop
MBJ5:33 pmMontego Bay Sangster Intl
Aug 27
MBJ12:55 pmMontego Bay Sangster Intl
10h 49m
1 stop
ORD11:44 pmChicago O'Hare Intl
$330
JetBlue
Aug 23
ORD7:00 amChicago O'Hare Intl
10h 33m
1 stop
MBJ5:33 pmMontego Bay Sangster Intl
Aug 26
MBJ12:55 pmMontego Bay Sangster Intl
10h 49m
1 stop
ORD11:44 pmChicago O'Hare Intl
$346

United Airlines flights from Illinois to Jamaica

Our best United Airlines deals on Illinois to Jamaica flight tickets
United Airlines
Aug 1
ORD6:30 amChicago O'Hare Intl
7h 00m
1 stop
MBJ1:30 pmMontego Bay Sangster Intl
Aug 8
MBJ4:33 pmMontego Bay Sangster Intl
8h 12m
1 stop
ORD12:45 amChicago O'Hare Intl
$372
United Airlines
Jun 2
ORD6:30 amChicago O'Hare Intl
8h 40m
1 stop
MBJ3:10 pmMontego Bay Sangster Intl
Jun 9
MBJ4:12 pmMontego Bay Sangster Intl
7h 14m
1 stop
ORD11:26 pmChicago O'Hare Intl
$374
United Airlines
May 30
ORD7:45 amChicago O'Hare Intl
7h 25m
1 stop
MBJ3:10 pmMontego Bay Sangster Intl
Jun 2
MBJ4:12 pmMontego Bay Sangster Intl
7h 14m
1 stop
ORD11:26 pmChicago O'Hare Intl
$379

momondo Fare Finder

 
Customize your flight search to find flights from Illinois 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 10, 2026.
Use the filters below to find and compare flights from Illinois to Jamaica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 8/25

7:00 am-5:33 pm

1 stop10h 33m

Montego Bay Sangster Intl

Thu 8/27

12:55 pm-11:44 pm

1 stop10h 49m

$324

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 8/9

7:00 am-5:33 pm

1 stop10h 33m

Montego Bay Sangster Intl

Thu 8/27

12:55 pm-11:44 pm

1 stop10h 49m

$330
Quickest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 11/3

9:45 am-3:01 pm

Nonstop4h 16m

Montego Bay Sangster Intl

Tue 11/10

3:14 pm-6:55 pm

Nonstop4h 41m

$338

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 11/3

5:00 am-12:54 pm

1 stop6h 54m

Montego Bay Sangster Intl

Tue 11/10

2:19 pm-6:00 pm

Nonstop4h 41m

$342

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 8/19

6:00 am-12:21 pm

1 stop6h 21m

Montego Bay Sangster Intl

Tue 8/25

1:26 pm-10:11 pm

1 stop8h 45m

$372

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 8/18

12:27 pm-12:21 pm

1 stop23h 54m

Montego Bay Sangster Intl

Tue 8/25

1:26 pm-10:11 pm

1 stop8h 45m

$390

MolineMontego Bay

MLI - MBJ

MLIMBJ

Moline Quad-City

Mon 9/21

2:29 pm-11:43 am

2 stops21h 14m

Montego Bay Sangster Intl

Thu 9/24

12:52 pm-10:14 am

2 stops21h 22m

$487

MolineMontego Bay

MLI - MBJ

MLIMBJ

Moline Quad-City

Mon 6/8

6:30 pm-3:10 pm

2 stops20h 40m

Montego Bay Sangster Intl

Sun 6/14

4:33 pm-11:16 pm

2 stops30h 43m

$497

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 7/22

2:35 pm-9:20 pm

1 stop6h 45m

Kingston Norman Manley

Tue 7/28

3:05 pm-9:00 am

1 stop17h 55m

$511

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 9/19

3:40 pm-1:55 pm

2 stops46h 15m

Kingston Norman Manley

Sat 9/26

4:05 pm-11:44 pm

1 stop7h 39m

$530

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 Illinois 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 Illinois 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 Illinois because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $636.

What is the cheapest Illinois to Jamaica flight route?

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

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

You are more likely to see cheaper flights to Jamaica from Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Jamaica for around $529 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Jamaica from Illinois for as low as $471 on momondo.

Can stopping save me money on Illinois to Jamaica flights?

You could potentially save up to 21% on your flight if you consider stops on a Illinois to Jamaica flight.

Cheap Illinois to Jamaica flight deals and tips

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

Best Price Found

$138

Fastest flight time

3h 40m

Direct flights

Every day

Airports in Jamaica

11 airports
The best one-way flight to Jamaica from Illinois in the past 72 hours is $138. The best round-trip flight deal from Illinois to Jamaica found on momondo in the last 72 hours is $317.
The fastest flight from Illinois to Jamaica takes 3h 40m
Direct flights go from Illinois to Jamaica every day.
There are 11 airports in Jamaica. From Illinois there are direct flights to Montego Bay Sangster Intl (MBJ).
Search flight deals

Frequently asked questions about flying from Illinois to Jamaica

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

    Prices for flights from Illinois to Jamaica are refreshed on a daily basis.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Illinois to Jamaica.

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

    The travel and health documents you'll need for your trip to Jamaica may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Jamaica. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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

Best airlines flying from Illinois to Jamaica

Compare and see reviews for airlines that fly from Illinois to Jamaica with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $100Free CancellationRating
6.3
8,636 reviews
Search Spirit Airlines flights
FrontierPriceFrom $144Free CancellationRating
5.6
2,957 reviews
Search Frontier flights
DeltaPriceFrom $178Free CancellationRating
7.9
8,455 reviews
Search Delta flights
United AirlinesPriceFrom $302Free CancellationRating
7.4
9,694 reviews
Search United Airlines flights
American AirlinesPriceFrom $321Free CancellationRating
7.1
11,667 reviews
Search American Airlines flights
SouthwestPriceFrom $468Free CancellationRating
8.0
4,306 reviews
Search Southwest flights

Why use momondo?

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

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

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

Flights from Illinois 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 Illinois 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 Illinois to Jamaica.

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

If you are simply researching potential flights to Jamaica, momondo offers a useful price alert feature which will track prices for flights to Jamaica from Illinois and alert you when they change.

An easier way to manage your Jamaica trip

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