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Cheap flights from Jamaica to Chicago from $169

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Jamaica to Chicago departing on 9/10. 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 Jamaica to Chicago

Recent round-trip flight deals from Jamaica to Chicago

Spirit Airlines Logo
12:19 pm - 7:07 pmMBJ-ORD
6h 48m1 stop
Spirit Airlines Logo
5:05 am - 11:05 amORD-MBJ
6h 00m1 stop
$294Spirit Airlines
Find Deal
Wed, Aug 13 - Wed, Oct 15
Spirit Airlines Logo
12:10 pm - 10:48 pmMBJ-ORD
10h 38m1 stop
Spirit Airlines Logo
6:44 pm - 11:05 amORD-MBJ
16h 21m1 stop
$301Spirit Airlines
Find Deal
Thu, Oct 2 - Mon, Oct 6
Spirit Airlines Logo
12:19 pm - 7:07 pmMBJ-ORD
6h 48m1 stop
Spirit Airlines Logo
5:05 am - 11:14 amORD-MBJ
6h 09m1 stop
$318Spirit Airlines
Find Deal
Wed, Aug 20 - Sun, Aug 24
Delta Logo
9:00 am - 4:31 pmKIN-ORD
7h 31m1 stop
Delta Logo
9:10 am - 8:00 pmORD-KIN
10h 50m2 stops
$330Delta
Find Deal
Fri, Sep 12 - Fri, Sep 19
Logo
10:22 am - 7:07 pmMBJ-ORD
8h 45m1 stop
Logo
6:00 pm - 7:55 amORD-MBJ
13h 55m1 stop
$348
Find Deal
Thu, Aug 14 - Thu, Aug 21
Frontier Logo
2:12 pm - 12:10 amMBJ-ORD
9h 58m1 stop
Frontier Logo
5:10 am - 12:41 pmORD-MBJ
7h 31m1 stop
$362Frontier
Find Deal
Sun, Sep 14 - Sun, Sep 21
American Airlines Logo
1:55 pm - 11:48 pmMBJ-ORD
9h 53m2 stops
American Airlines Logo
6:52 pm - 10:32 amORD-MBJ
15h 40m1 stop
$378American Airlines
Find Deal
Fri, Sep 12 - Fri, Sep 19
Frontier Logo
2:12 pm - 12:10 amMBJ-ORD
9h 58m1 stop
Frontier Logo
8:49 pm - 12:45 pmORD-MBJ
15h 56m2 stops
$383Frontier
Find Deal
Sun, Sep 14 - Sun, Sep 21
American Airlines Logo
1:00 pm - 9:22 pmKIN-ORD
8h 22m1 stop
American Airlines Logo
8:20 am - 7:38 pmORD-KIN
11h 18m2 stops
$416American Airlines
Find Deal
Sat, Sep 13 - Sat, Sep 20
Logo
12:19 pm - 7:07 pmMBJ-ORD
6h 48m1 stop
Logo
5:17 pm - 1:20 pmORD-MBJ
20h 03m2 stops
$437
Find Deal
Wed, Aug 13 - Mon, Oct 13

American Airlines flights from Jamaica to Chicago O'Hare Intl Airport

Our best American Airlines deals on Jamaica to Chicago O'Hare Intl Airport flight tickets
American Airlines
Sep 12
MBJ1:55 pmMontego Bay Sangster Intl
9h 53m
2 stops
ORD11:48 pmChicago O'Hare Intl
Sep 19
ORD6:52 pmChicago O'Hare Intl
15h 40m
1 stop
MBJ10:32 amMontego Bay Sangster Intl
$378
Find similar
American Airlines
Sep 13
KIN1:00 pmKingston Norman Manley
8h 22m
1 stop
ORD9:22 pmChicago O'Hare Intl
Sep 20
ORD8:20 amChicago O'Hare Intl
11h 18m
2 stops
KIN7:38 pmKingston Norman Manley
$416
Find similar
American Airlines
Oct 2
MBJ2:38 pmMontego Bay Sangster Intl
7h 48m
1 stop
ORD10:26 pmChicago O'Hare Intl
Oct 6
ORD8:40 amChicago O'Hare Intl
4h 01m
MBJ12:41 pmMontego Bay Sangster Intl
$460
Find similar

Frontier flights from Jamaica to Chicago O'Hare Intl Airport

Our best Frontier deals on Jamaica to Chicago O'Hare Intl Airport flight tickets
Frontier
Aug 7
MBJ9:10 amMontego Bay Sangster Intl
15h 12m
1 stop
ORD12:22 amChicago O'Hare Intl
Aug 12
ORD5:38 pmChicago O'Hare Intl
14h 17m
1 stop
MBJ7:55 amMontego Bay Sangster Intl
$359
Find similar
Frontier
Sep 14
MBJ2:12 pmMontego Bay Sangster Intl
9h 58m
1 stop
ORD12:10 amChicago O'Hare Intl
Sep 21
ORD5:10 amChicago O'Hare Intl
7h 31m
1 stop
MBJ12:41 pmMontego Bay Sangster Intl
$362
Find similar
Frontier
Aug 7
MBJ9:10 amMontego Bay Sangster Intl
15h 12m
1 stop
ORD12:22 amChicago O'Hare Intl
Aug 11
ORD5:01 amChicago O'Hare Intl
9h 39m
1 stop
MBJ2:40 pmMontego Bay Sangster Intl
$369
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Jamaica to Chicago O'Hare Intl Airport 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 July 31, 2025.
Use the filters below to find and compare flights from Jamaica to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 8/13

12:19 pm-7:07 pm

1 stop6h 48m

Chicago O'Hare Intl

Wed 10/15

5:05 am-11:05 am

1 stop6h 00m

$294

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 10/2

12:10 pm-10:48 pm

1 stop10h 38m

Chicago O'Hare Intl

Mon 10/6

6:44 pm-11:05 am

1 stop16h 21m

$301

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 8/20

12:19 pm-7:07 pm

1 stop6h 48m

Chicago O'Hare Intl

Sun 8/24

5:05 am-11:14 am

1 stop6h 09m

$318

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Fri 9/12

9:00 am-4:31 pm

1 stop7h 31m

Chicago O'Hare Intl

Fri 9/19

9:10 am-8:00 pm

2 stops10h 50m

$330

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 8/14

10:22 am-7:07 pm

1 stop8h 45m

Chicago O'Hare Intl

Thu 8/21

6:00 pm-7:55 am

1 stop13h 55m

$348

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sun 9/14

2:12 pm-12:10 am

1 stop9h 58m

Chicago O'Hare Intl

Sun 9/21

5:10 am-12:41 pm

1 stop7h 31m

$362

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 9/12

1:55 pm-11:48 pm

2 stops9h 53m

Chicago O'Hare Intl

Fri 9/19

6:52 pm-10:32 am

1 stop15h 40m

$378

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sun 9/14

2:12 pm-12:10 am

1 stop9h 58m

Chicago O'Hare Intl

Sun 9/21

8:49 pm-12:45 pm

2 stops15h 56m

$383

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Sat 9/13

1:00 pm-9:22 pm

1 stop8h 22m

Chicago O'Hare Intl

Sat 9/20

8:20 am-7:38 pm

2 stops11h 18m

$416

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 8/13

12:19 pm-7:07 pm

1 stop6h 48m

Chicago O'Hare Intl

Mon 10/13

5:17 pm-1:20 pm

2 stops20h 03m

$437

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Jamaica to Chicago O'Hare Intl Airport

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 Chicago O'Hare Intl Airport?

The month of September is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Jamaica averaging around $424.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $445. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Jamaica because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $634.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Jamaica in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $446 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $492. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Jamaica to Chicago O'Hare Intl flight route?

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

What cabin class options are available on Jamaica to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Jamaica to Chicago O'Hare Intl 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 Jamaica to Chicago O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between Jamaica to Chicago O'Hare Intl Airport.

Cheap Jamaica to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Jamaica to Chicago O'Hare Intl Airport

Best Price Found

$169

Fastest flight time

4h 28m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Jamaica in the past 72 hours is $169. The best round-trip flight deal from Jamaica to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $294.
The fastest flight from Jamaica to Chicago O'Hare Intl Airport takes 4h 28m
Direct flights go from Jamaica to Chicago O'Hare Intl Airport every day.
Search flight deals

  • When did momondo last update prices for flights from Jamaica to Chicago O'Hare Intl Airport?

    Prices for flights from Jamaica to Chicago O'Hare Intl Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Jamaica to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Jamaica to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Jamaica to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents required for your trip to Chicago O'Hare Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago O'Hare Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Jamaica to Chicago O'Hare Intl Airport?

Best airlines flying from Jamaica to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Jamaica to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $251Free CancellationRating
6.3
8,048 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $255Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights
DeltaPriceFrom $322Free CancellationRating
8.0
7,981 reviews
Search Delta flights
American AirlinesPriceFrom $392Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

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Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
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Rosemont
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Racine
Hammond
Tinley Park
Elgin
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Aurora
Janesville
Benton Harbor

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Jamaica to Chicago. momondo saves you time and could save you money on your trip.

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

All flight searches from Jamaica to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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

momondo provides multiple filters to help you find the best flight to Chicago from Jamaica. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Yes. momondo can track prices for Jamaica to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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