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Cheap flights from Jamaica to Chicago from $163

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 4/24. 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

Enter your travel dates to find the best prices.
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
American Airlines Logo
4:56 pm - 9:25 am
ORD
-
MBJ
16h 29m
1 stop
$246American Airlines
Fri, May 15 - Sat, Sep 5
American Airlines Logo
10:17 am - 10:44 am
MBJ
-
ORD
24h 27m
1 stop
American Airlines Logo
6:25 pm - 9:25 am
ORD
-
MBJ
15h 00m
1 stop
$262American Airlines
Fri, May 15 - Sat, Sep 5
American Airlines Logo
3:04 pm - 8:38 am
MBJ
-
ORD
17h 34m
1 stop
American Airlines Logo
6:10 am - 2:04 pm
ORD
-
MBJ
7h 54m
1 stop
$266American Airlines
Mon, Mar 30 - Sun, Apr 5
Spirit Airlines Logo
12:00 pm - 8:03 am
MBJ
-
ORD
20h 03m
2 stops
Spirit Airlines Logo
5:05 am - 10:59 am
ORD
-
MBJ
5h 54m
1 stop
$333Spirit Airlines
Mon, May 18 - Sun, May 31
Copa Airlines Logo
12:20 pm - 1:04 am
MBJ
-
ORD
12h 44m
1 stop
Copa Airlines Logo
3:22 pm - 10:11 am
ORD
-
MBJ
18h 49m
1 stop
$338Copa Airlines
Tue, Mar 10 - Fri, Mar 13
Multiple Airlines Logo
12:00 pm - 7:47 pm
MBJ
-
ORD
7h 47m
1 stop
Multiple Airlines Logo
8:40 pm - 11:20 am
ORD
-
MBJ
14h 40m
1 stop
$344Multiple Airlines
Wed, May 6 - Thu, Sep 10
Multiple Airlines Logo
12:32 pm - 10:50 pm
KIN
-
ORD
10h 18m
1 stop
Multiple Airlines Logo
1:27 pm - 11:06 am
ORD
-
KIN
21h 39m
1 stop
$345Multiple Airlines
Thu, Apr 9 - Thu, Apr 16
Multiple Airlines Logo
12:00 pm - 8:03 am
MBJ
-
ORD
20h 03m
2 stops
Multiple Airlines Logo
2:15 pm - 11:20 am
ORD
-
MBJ
21h 05m
1 stop
$361Multiple Airlines
Wed, May 6 - Thu, Sep 10
Spirit Airlines Logo
12:11 pm - 11:22 am
KIN
-
ORD
23h 11m
1 stop
Spirit Airlines Logo
5:34 pm - 11:06 am
ORD
-
KIN
17h 32m
1 stop
$363Spirit Airlines
Mon, May 18 - Sun, May 31
Frontier Logo
1:57 pm - 10:54 am
MBJ
-
ORD
20h 57m
1 stop
Frontier Logo
4:28 pm - 12:12 pm
ORD
-
MBJ
19h 44m
1 stop
$371Frontier
Mon, Apr 6 - Fri, Apr 24

Delta flights from Jamaica to Chicago

Our best Delta deals on Jamaica to Chicago flight tickets
Delta
May 15
MBJ2:21 pmMontego Bay Sangster Intl
9h 38m
1 stop
ORD11:59 pmChicago O'Hare Intl
Sep 6
ORD6:10 pmChicago O'Hare Intl
17h 14m
1 stop
MBJ11:24 amMontego Bay Sangster Intl
$415
Delta
Apr 20
KIN9:00 amKingston Norman Manley
11h 40m
2 stops
ORD8:40 pmChicago O'Hare Intl
Apr 29
ORD9:50 amChicago O'Hare Intl
10h 10m
1 stop
KIN8:00 pmKingston Norman Manley
$451
Delta
Apr 20
KIN9:00 amKingston Norman Manley
11h 40m
2 stops
ORD8:40 pmChicago O'Hare Intl
Apr 29
ORD8:52 amChicago O'Hare Intl
11h 08m
2 stops
KIN8:00 pmKingston Norman Manley
$521

American Airlines flights from Jamaica to Chicago

Our best American Airlines deals on Jamaica to Chicago flight tickets
American Airlines
Jun 4
MBJ2:23 pmMontego Bay Sangster Intl
4h 47m
ORD7:10 pmChicago O'Hare Intl
Oct 6
ORD8:05 amChicago O'Hare Intl
4h 01m
MBJ12:06 pmMontego Bay Sangster Intl
$241
American Airlines
May 15
MBJ1:15 pmMontego Bay Sangster Intl
4h 40m
ORD5:55 pmChicago O'Hare Intl
Sep 5
ORD4:56 pmChicago O'Hare Intl
16h 29m
1 stop
MBJ9:25 amMontego Bay Sangster Intl
$246
American Airlines
May 29
MBJ3:02 pmMontego Bay Sangster Intl
9h 30m
1 stop
ORD12:32 amChicago O'Hare Intl
Aug 31
ORD8:30 amChicago O'Hare Intl
4h 01m
MBJ12:31 pmMontego Bay Sangster Intl
$252

momondo Fare Finder

 
Customize your flight search to find flights from Jamaica to Chicago 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 February 27, 2026.
Use the filters below to find and compare flights from Jamaica to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 5/15

1:15 pm-5:55 pm

Nonstop4h 40m

Chicago O'Hare Intl

Sat 9/5

4:56 pm-9:25 am

1 stop16h 29m

$246

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 5/15

10:17 am-10:44 am

1 stop24h 27m

Chicago O'Hare Intl

Sat 9/5

6:25 pm-9:25 am

1 stop15h 00m

$262

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 3/30

3:04 pm-8:38 am

1 stop17h 34m

Chicago O'Hare Intl

Sun 4/5

6:10 am-2:04 pm

1 stop7h 54m

$266

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 5/18

12:00 pm-8:03 am

2 stops20h 03m

Chicago O'Hare Intl

Sun 5/31

5:05 am-10:59 am

1 stop5h 54m

$333

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 3/10

12:20 pm-1:04 am

1 stop12h 44m

Chicago O'Hare Intl

Fri 3/13

3:22 pm-10:11 am

1 stop18h 49m

$338

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 5/6

12:00 pm-7:47 pm

1 stop7h 47m

Chicago O'Hare Intl

Thu 9/10

8:40 pm-11:20 am

1 stop14h 40m

$344

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Thu 4/9

12:32 pm-10:50 pm

1 stop10h 18m

Chicago O'Hare Intl

Thu 4/16

1:27 pm-11:06 am

1 stop21h 39m

$345

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 5/6

12:00 pm-8:03 am

2 stops20h 03m

Chicago O'Hare Intl

Thu 9/10

2:15 pm-11:20 am

1 stop21h 05m

$361

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Mon 5/18

12:11 pm-11:22 am

1 stop23h 11m

Chicago O'Hare Intl

Sun 5/31

5:34 pm-11:06 am

1 stop17h 32m

$363

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 4/6

1:57 pm-10:54 am

1 stop20h 57m

Chicago O'Hare Intl

Fri 4/24

4:28 pm-12:12 pm

1 stop19h 44m

$371

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

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?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $441. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Jamaica to Chicago for around $633.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Jamaica to Chicago during this time can be as low as $468. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $498.

What is the cheapest Jamaica to Chicago flight route?

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

What cabin class options are available on Jamaica to Chicago flights?

There are 3 cabin classes available to choose from on Jamaica to Chicago 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 flights?

You could potentially save up to 10% on your flight if you consider stops on a Jamaica to Chicago flight.

Cheap Jamaica to Chicago flight deals and tips

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

Best Price Found

$277

Fastest flight time

4h 23m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Jamaica in the past 72 hours is $277. The best round-trip flight deal from Jamaica to Chicago found on momondo in the last 72 hours is $365.
The fastest flight from Jamaica to Chicago takes 4h 23m
Direct flights go from Jamaica to Chicago every day.
There are 3 airports in Chicago. From Jamaica there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

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

    Prices for flights from Jamaica to Chicago refresh daily.

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Jamaica to Chicago.

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

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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

Best airlines flying from Jamaica to Chicago

Compare and see reviews for airlines that fly from Jamaica to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $256Free CancellationRating
6.3
8,493 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $348Free CancellationRating
7.1
11,363 reviews
Search American Airlines flights
United AirlinesPriceFrom $349Free CancellationRating
7.4
9,358 reviews
Search United Airlines flights
SouthwestPriceFrom $392Free CancellationRating
8.0
4,301 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

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

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

Yes. momondo allows you to filter the results for Jamaica to Chicago flights to just show those with 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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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport