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Cheap flights from Jamaica to Chicago from $199

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 12/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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.
American Airlines Logo
3:14 pm - 6:55 pm
MBJ
-
ORD
4h 41mnonstop
American Airlines Logo
8:05 am - 1:14 pm
ORD
-
MBJ
4h 09mnonstop
$311American Airlines
Thu, Nov 19 - Sun, Nov 29
Delta Logo
1:32 pm - 8:20 pm
MBJ
-
ORD
6h 48m
1 stop
Delta Logo
7:10 am - 1:20 pm
ORD
-
MBJ
6h 10m
1 stop
$317Delta
Fri, Oct 16 - Mon, Oct 19
United Airlines Logo
2:48 pm - 6:16 pm
MBJ
-
ORD
4h 28mnonstop
United Airlines Logo
8:42 am - 1:46 pm
ORD
-
MBJ
4h 04mnonstop
$321United Airlines
Mon, Nov 23 - Sun, Nov 29
American Airlines Logo
4:05 pm - 11:08 pm
MBJ
-
ORD
8h 03m
1 stop
American Airlines Logo
8:05 am - 1:14 pm
ORD
-
MBJ
4h 09mnonstop
$322American Airlines
Thu, Nov 19 - Sun, Nov 29
American Airlines Logo
2:12 pm - 6:55 pm
MBJ
-
ORD
4h 43mnonstop
American Airlines Logo
5:00 am - 4:08 pm
ORD
-
MBJ
11h 08m
1 stop
$326American Airlines
Sat, Aug 29 - Sat, Sep 5
American Airlines Logo
3:23 pm - 11:44 pm
MBJ
-
ORD
8h 21m
1 stop
American Airlines Logo
9:00 am - 1:12 pm
ORD
-
MBJ
4h 12mnonstop
$332American Airlines
Thu, Aug 13 - Mon, Aug 17
American Airlines Logo
3:23 pm - 11:44 pm
MBJ
-
ORD
8h 21m
1 stop
American Airlines Logo
7:30 am - 1:28 pm
ORD
-
MBJ
5h 58m
1 stop
$336American Airlines
Thu, Aug 13 - Mon, Aug 17
American Airlines Logo
5:08 pm - 7:34 am
MBJ
-
ORD
14h 26m
1 stop
American Airlines Logo
5:20 am - 12:53 pm
ORD
-
MBJ
7h 33m
2 stops
$341American Airlines
Mon, Sep 7 - Mon, Sep 28
JetBlue Logo
12:08 pm - 11:44 pm
KIN
-
ORD
11h 36m
1 stop
JetBlue Logo
7:00 am - 5:18 pm
ORD
-
KIN
10h 18m
1 stop
$478JetBlue
Sat, Jul 18 - Sat, Jul 25
JetBlue Logo
12:08 pm - 11:44 pm
KIN
-
ORD
11h 36m
1 stop
JetBlue Logo
2:35 pm - 9:17 pm
ORD
-
KIN
6h 42m
1 stop
$516JetBlue
Wed, Jul 15 - Sat, Jul 25

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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
Nov 19
MBJ3:14 pmMontego Bay Sangster Intl
4h 41m
ORD6:55 pmChicago O'Hare Intl
Nov 29
ORD8:05 amChicago O'Hare Intl
4h 09m
MBJ1:14 pmMontego Bay Sangster Intl
$311
American Airlines
Jun 25
MBJ2:31 pmMontego Bay Sangster Intl
4h 39m
ORD7:10 pmChicago O'Hare Intl
Jul 4
ORD9:20 amChicago O'Hare Intl
4h 16m
MBJ1:36 pmMontego Bay Sangster Intl
$320
American Airlines
Nov 19
MBJ4:05 pmMontego Bay Sangster Intl
8h 03m
1 stop
ORD11:08 pmChicago O'Hare Intl
Nov 29
ORD8:05 amChicago O'Hare Intl
4h 09m
MBJ1:14 pmMontego Bay Sangster Intl
$322

Delta flights from Jamaica to Chicago O'Hare Intl Airport

Our best Delta deals on Jamaica to Chicago O'Hare Intl Airport flight tickets
Delta
Oct 16
MBJ1:32 pmMontego Bay Sangster Intl
6h 48m
1 stop
ORD8:20 pmChicago O'Hare Intl
Oct 19
ORD7:10 amChicago O'Hare Intl
6h 10m
1 stop
MBJ1:20 pmMontego Bay Sangster Intl
$317
Delta
Nov 23
MBJ6:00 pmMontego Bay Sangster Intl
6h 50m
1 stop
ORD11:50 pmChicago O'Hare Intl
Nov 29
ORD5:30 amChicago O'Hare Intl
10h 05m
1 stop
MBJ4:35 pmMontego Bay Sangster Intl
$401
Delta
Nov 23
MBJ6:00 pmMontego Bay Sangster Intl
6h 50m
1 stop
ORD11:50 pmChicago O'Hare Intl
Nov 29
ORD5:30 amChicago O'Hare Intl
10h 05m
1 stop
MBJ4:35 pmMontego Bay Sangster Intl
$533

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 June 20, 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

Cheapest round-trip

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 11/19

3:14 pm-6:55 pm

Nonstop4h 41m

Chicago O'Hare Intl

Sun 11/29

8:05 am-1:14 pm

Nonstop4h 09m

$311

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 10/16

1:32 pm-8:20 pm

1 stop6h 48m

Chicago O'Hare Intl

Mon 10/19

7:10 am-1:20 pm

1 stop6h 10m

$317
Quickest round-trip

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 11/23

2:48 pm-6:16 pm

Nonstop4h 28m

Chicago O'Hare Intl

Sun 11/29

8:42 am-1:46 pm

Nonstop4h 04m

$321

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 11/19

4:05 pm-11:08 pm

1 stop8h 03m

Chicago O'Hare Intl

Sun 11/29

8:05 am-1:14 pm

Nonstop4h 09m

$322

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 8/29

2:12 pm-6:55 pm

Nonstop4h 43m

Chicago O'Hare Intl

Sat 9/5

5:00 am-4:08 pm

1 stop11h 08m

$326

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 8/13

3:23 pm-11:44 pm

1 stop8h 21m

Chicago O'Hare Intl

Mon 8/17

9:00 am-1:12 pm

Nonstop4h 12m

$332

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 8/13

3:23 pm-11:44 pm

1 stop8h 21m

Chicago O'Hare Intl

Mon 8/17

7:30 am-1:28 pm

1 stop5h 58m

$336

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 9/7

5:08 pm-7:34 am

1 stop14h 26m

Chicago O'Hare Intl

Mon 9/28

5:20 am-12:53 pm

2 stops7h 33m

$341

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Sat 7/18

12:08 pm-11:44 pm

1 stop11h 36m

Chicago O'Hare Intl

Sat 7/25

7:00 am-5:18 pm

1 stop10h 18m

$478

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 7/15

12:08 pm-11:44 pm

1 stop11h 36m

Chicago O'Hare Intl

Sat 7/25

2:35 pm-9:17 pm

1 stop6h 42m

$516

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 month to fly to Chicago O'Hare Intl Airport?

The month of April is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Jamaica averaging around $146.

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 Thursday when prices can be found for as low as $386. 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 $537.

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 $445 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $454. 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 Airport flights?

There are 3 cabin classes available to choose from on Jamaica to Chicago O'Hare Intl Airport 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 11% 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

$286

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 $286. The best round-trip flight deal from Jamaica to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $426.
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

Frequently asked questions about flying from Jamaica to Chicago O'Hare Intl Airport

  • 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
United AirlinesPriceFrom $280Free CancellationRating
7.4
9,865 reviews
Search United Airlines flights
American AirlinesPriceFrom $281Free CancellationRating
7.1
11,715 reviews
Search American 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
Rosemont
Naperville
Orland Park
Oak Brook
New Buffalo
Joliet
Kenosha
Aurora
Hammond
Racine
Janesville
Evanston
Elgin
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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