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Cheap flights from Jamaica to Chicago from $149

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 2/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Jamaica to Chicago

Recent round-trip flight deals from Jamaica to Chicago

Enter your travel dates to find the best prices.
Spirit Airlines Logo
1:00 pm - 9:13 pm
MBJ
-
ORD
9h 13m
1 stop
Spirit Airlines Logo
5:15 am - 12:02 pm
ORD
-
MBJ
5h 47m
1 stop
$230Spirit Airlines
Wed, Feb 25 - Wed, Mar 4
Spirit Airlines Logo
12:00 pm - 7:46 pm
MBJ
-
ORD
7h 46m
1 stop
Spirit Airlines Logo
8:41 pm - 11:02 am
ORD
-
MBJ
14h 21m
1 stop
$269Spirit Airlines
Tue, Mar 24 - Tue, Apr 14
American Airlines Logo
1:14 pm - 5:55 pm
MBJ
-
ORD
4h 41mnonstop
American Airlines Logo
8:10 am - 12:15 pm
ORD
-
MBJ
4h 05mnonstop
$320American Airlines
Tue, Mar 24 - Tue, Apr 14
United Airlines Logo
1:48 pm - 6:13 pm
MBJ
-
ORD
4h 25mnonstop
United Airlines Logo
8:45 am - 3:10 pm
ORD
-
MBJ
6h 25m
1 stop
$325United Airlines
Tue, Mar 24 - Tue, Apr 14
Spirit Airlines Logo
1:00 pm - 7:54 am
MBJ
-
ORD
19h 54m
2 stops
Spirit Airlines Logo
5:15 am - 12:02 pm
ORD
-
MBJ
5h 47m
1 stop
$329Spirit Airlines
Wed, Feb 25 - Wed, Mar 4
American Airlines Logo
3:20 pm - 11:53 pm
MBJ
-
ORD
8h 33m
1 stop
American Airlines Logo
6:58 pm - 11:51 am
ORD
-
MBJ
16h 53m
1 stop
$335American Airlines
Thu, May 14 - Mon, May 18
American Airlines Logo
1:15 pm - 5:58 pm
MBJ
-
ORD
4h 43mnonstop
American Airlines Logo
8:10 am - 12:15 pm
ORD
-
MBJ
4h 05mnonstop
$345American Airlines
Mon, Apr 13 - Tue, Apr 21
Delta Logo
11:15 am - 11:54 pm
MBJ
-
ORD
12h 39m
1 stop
Delta Logo
7:00 am - 3:17 pm
ORD
-
MBJ
8h 17m
2 stops
$351Delta
Tue, Mar 24 - Tue, Apr 14
Multiple Airlines Logo
12:00 pm - 9:17 pm
KIN
-
ORD
9h 17m
1 stop
Multiple Airlines Logo
5:32 pm - 11:05 am
ORD
-
KIN
17h 33m
1 stop
$372Multiple Airlines
Tue, May 19 - Mon, Aug 31
Multiple Airlines Logo
12:00 pm - 9:17 pm
KIN
-
ORD
9h 17m
1 stop
Multiple Airlines Logo
5:32 pm - 11:05 am
ORD
-
KIN
17h 33m
1 stop
$383Multiple Airlines
Tue, May 19 - Mon, Aug 31

Air Canada flights from Jamaica to Chicago O'Hare Intl Airport

Our best Air Canada deals on Jamaica to Chicago O'Hare Intl Airport flight tickets
Air Canada
Apr 13
MBJ12:40 pmMontego Bay Sangster Intl
23h 37m
2 stops
ORD12:17 pmChicago O'Hare Intl
Apr 21
ORD8:20 pmChicago O'Hare Intl
15h 15m
1 stop
MBJ11:35 amMontego Bay Sangster Intl
$409
Air Canada
May 15
KIN3:05 pmKingston Norman Manley
27h 48m
2 stops
ORD6:53 pmChicago O'Hare Intl
May 19
ORD9:55 amChicago O'Hare Intl
28h 00m
1 stop
KIN1:55 pmKingston Norman Manley
$431
Air Canada
Mar 30
MBJ12:40 pmMontego Bay Sangster Intl
21h 10m
1 stop
ORD9:50 amChicago O'Hare Intl
Apr 6
ORD6:21 pmChicago O'Hare Intl
41h 14m
2 stops
MBJ11:35 amMontego Bay Sangster Intl
$447

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
Mar 24
MBJ1:14 pmMontego Bay Sangster Intl
4h 41m
ORD5:55 pmChicago O'Hare Intl
Apr 14
ORD8:10 amChicago O'Hare Intl
4h 05m
MBJ12:15 pmMontego Bay Sangster Intl
$320
American Airlines
May 14
MBJ3:20 pmMontego Bay Sangster Intl
8h 33m
1 stop
ORD11:53 pmChicago O'Hare Intl
May 18
ORD6:58 pmChicago O'Hare Intl
16h 53m
1 stop
MBJ11:51 amMontego Bay Sangster Intl
$335
American Airlines
Apr 13
MBJ1:15 pmMontego Bay Sangster Intl
4h 43m
ORD5:58 pmChicago O'Hare Intl
Apr 21
ORD8:10 amChicago O'Hare Intl
4h 05m
MBJ12:15 pmMontego Bay Sangster Intl
$345

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 January 29, 2026.
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 2/25

1:00 pm-9:13 pm

1 stop9h 13m

Chicago O'Hare Intl

Wed 3/4

5:15 am-12:02 pm

1 stop5h 47m

$230

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 3/24

12:00 pm-7:46 pm

1 stop7h 46m

Chicago O'Hare Intl

Tue 4/14

8:41 pm-11:02 am

1 stop14h 21m

$269

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 3/24

1:14 pm-5:55 pm

Nonstop4h 41m

Chicago O'Hare Intl

Tue 4/14

8:10 am-12:15 pm

Nonstop4h 05m

$320

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 3/24

1:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

Tue 4/14

8:45 am-3:10 pm

1 stop6h 25m

$325

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 2/25

1:00 pm-7:54 am

2 stops19h 54m

Chicago O'Hare Intl

Wed 3/4

5:15 am-12:02 pm

1 stop5h 47m

$329

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 5/14

3:20 pm-11:53 pm

1 stop8h 33m

Chicago O'Hare Intl

Mon 5/18

6:58 pm-11:51 am

1 stop16h 53m

$335

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 4/13

1:15 pm-5:58 pm

Nonstop4h 43m

Chicago O'Hare Intl

Tue 4/21

8:10 am-12:15 pm

Nonstop4h 05m

$345

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 3/24

11:15 am-11:54 pm

1 stop12h 39m

Chicago O'Hare Intl

Tue 4/14

7:00 am-3:17 pm

2 stops8h 17m

$351

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 5/19

12:00 pm-9:17 pm

1 stop9h 17m

Chicago O'Hare Intl

Mon 8/31

5:32 pm-11:05 am

1 stop17h 33m

$372

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 5/19

12:00 pm-9:17 pm

1 stop9h 17m

Chicago O'Hare Intl

Mon 8/31

5:32 pm-11:05 am

1 stop17h 33m

$383

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 Chicago from

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 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 $438. This is often the case because there is less demand to fly during this day of the week. On the other hand, Friday 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 $557.

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 at noon is the least expensive time of day to depart. momondo users have found prices as low as $494 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $507. 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 3 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?

You could potentially save up to 25% on your flight if you consider stops on a Jamaica to Chicago O'Hare Intl Airport flight.

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

$282

Fastest flight time

4h 23m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Jamaica in the past 72 hours is $282. The best round-trip flight deal from Jamaica to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $365.
The fastest flight from Jamaica to Chicago O'Hare Intl Airport takes 4h 23m
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 $256Free CancellationRating
6.3
8,394 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $348Free CancellationRating
7.2
11,206 reviews
Search American Airlines flights
United AirlinesPriceFrom $349Free CancellationRating
7.4
9,215 reviews
Search United Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Naperville
Rosemont
New Buffalo
Kenosha
Joliet
Oak Brook
Orland Park
Racine
Hammond
Janesville
Tinley Park
Elgin
Aurora
South Holland

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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