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Cheap flights from Jamaica to Chicago from $159

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 5/20. 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
8:05 am - 12:13 pm
ORD
-
MBJ
4h 08mnonstop
$281American Airlines
ر, أبريل 29 - ث, مايو 5
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
American Airlines Logo
8:46 pm - 11:24 am
ORD
-
MBJ
14h 38m
1 stop
$286American Airlines
خ, أبريل 30 - ث, مايو 5
United Airlines Logo
4:12 pm - 7:27 am
MBJ
-
ORD
15h 15m
1 stop
United Airlines Logo
7:45 pm - 11:43 am
ORD
-
MBJ
15h 58m
1 stop
$290United Airlines
ر, مايو 20 - ن, سبتمبر 14
United Airlines Logo
2:40 pm - 1:26 am
MBJ
-
ORD
10h 46m
1 stop
United Airlines Logo
2:27 pm - 3:10 pm
ORD
-
MBJ
24h 43m
1 stop
$291United Airlines
خ, أبريل 30 - ر, مايو 6
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
$334Frontier
ر, مايو 20 - ث, مايو 26
Frontier Logo
1:26 pm - 10:11 pm
MBJ
-
MDW
8h 45m
1 stop
Frontier Logo
6:00 am - 12:21 pm
MDW
-
MBJ
6h 21m
1 stop
$354Frontier
ر, يونيو 17 - ح, يونيو 21
Southwest Logo
11:35 am - 3:45 pm
MBJ
-
MDW
4h 10mnonstop
Southwest Logo
9:55 am - 1:45 pm
MDW
-
MBJ
3h 50mnonstop
$399Southwest
س, مايو 23 - س, مايو 30
Southwest Logo
11:35 am - 3:45 pm
MBJ
-
MDW
4h 10mnonstop
Southwest Logo
6:10 am - 1:30 pm
MDW
-
MBJ
7h 20m
1 stop
$449Southwest
س, مايو 23 - س, مايو 30
Air Canada Logo
3:05 pm - 9:00 am
KIN
-
ORD
17h 55m
1 stop
Air Canada Logo
8:35 pm - 1:55 pm
ORD
-
KIN
17h 20m
1 stop
$463Air Canada
ث, مايو 19 - ث, مايو 26
Air Canada Logo
3:05 pm - 2:55 pm
KIN
-
ORD
23h 50m
1 stop
Air Canada Logo
8:45 am - 1:55 pm
ORD
-
KIN
29h 10m
2 stops
$466Air Canada
ث, مايو 19 - ث, مايو 26

JetBlue flights from Jamaica to Chicago

Our best JetBlue deals on Jamaica to Chicago flight tickets
JetBlue
May 22
KIN11:59 pmKingston Norman Manley
14h 17m
1 stop
ORD2:16 pmChicago O'Hare Intl
Sep 4
ORD9:39 amChicago O'Hare Intl
13h 39m
1 stop
KIN11:18 pmKingston Norman Manley
$580
JetBlue
May 13
KIN6:10 pmKingston Norman Manley
13h 34m
1 stop
ORD7:44 amChicago O'Hare Intl
May 26
ORD6:15 amChicago O'Hare Intl
12h 35m
1 stop
KIN6:50 pmKingston Norman Manley
$599
JetBlue
May 5
KIN6:03 pmKingston Norman Manley
14h 44m
1 stop
ORD8:47 amChicago O'Hare Intl
Sep 3
ORD9:39 amChicago O'Hare Intl
10h 35m
1 stop
KIN8:14 pmKingston Norman Manley
$739

United Airlines flights from Jamaica to Chicago

Our best United Airlines deals on Jamaica to Chicago flight tickets
United Airlines
May 20
MBJ4:12 pmMontego Bay Sangster Intl
7h 32m
1 stop
ORD11:44 pmChicago O'Hare Intl
Sep 12
ORD7:45 pmChicago O'Hare Intl
15h 58m
1 stop
MBJ11:43 amMontego Bay Sangster Intl
$290
United Airlines
May 16
MBJ2:40 pmMontego Bay Sangster Intl
17h 13m
1 stop
ORD7:53 amChicago O'Hare Intl
May 18
ORD9:56 pmChicago O'Hare Intl
15h 34m
1 stop
MBJ1:30 pmMontego Bay Sangster Intl
$291
United Airlines
May 23
MBJ2:40 pmMontego Bay Sangster Intl
8h 35m
1 stop
ORD11:15 pmChicago O'Hare Intl
May 30
ORD8:40 amChicago O'Hare Intl
4h 10m
MBJ12:50 pmMontego Bay Sangster Intl
$314

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 أبريل 26, 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

Cheapest round-trip

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

ر 4/29

1:15 pm-5:55 pm

Nonstop4h 40m

Chicago O'Hare Intl

ث 5/5

8:05 am-12:13 pm

Nonstop4h 08m

$281

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

خ 4/30

1:15 pm-5:55 pm

Nonstop4h 40m

Chicago O'Hare Intl

ث 5/5

8:46 pm-11:24 am

1 stop14h 38m

$286

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

ر 5/20

4:12 pm-7:27 am

1 stop15h 15m

Chicago O'Hare Intl

ن 9/14

7:45 pm-11:43 am

1 stop15h 58m

$290

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

خ 4/30

2:40 pm-1:26 am

1 stop10h 46m

Chicago O'Hare Intl

ر 5/6

2:27 pm-3:10 pm

1 stop24h 43m

$291

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

ر 5/20

1:16 pm-10:02 pm

1 stop8h 46m

Chicago Midway

ث 5/26

6:00 am-12:11 pm

1 stop6h 11m

$334

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

ر 6/17

1:26 pm-10:11 pm

1 stop8h 45m

Chicago Midway

ح 6/21

6:00 am-12:21 pm

1 stop6h 21m

$354
Quickest round-trip

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

س 5/23

11:35 am-3:45 pm

Nonstop4h 10m

Chicago Midway

س 5/30

9:55 am-1:45 pm

Nonstop3h 50m

$399

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

س 5/23

11:35 am-3:45 pm

Nonstop4h 10m

Chicago Midway

س 5/30

6:10 am-1:30 pm

1 stop7h 20m

$449

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

ث 5/19

3:05 pm-9:00 am

1 stop17h 55m

Chicago O'Hare Intl

ث 5/26

8:35 pm-1:55 pm

1 stop17h 20m

$463

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

ث 5/19

3:05 pm-2:55 pm

1 stop23h 50m

Chicago O'Hare Intl

ث 5/26

8:45 am-1:55 pm

2 stops29h 10m

$466

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 $419. 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 $543.

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 $454. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $477.

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 5% 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

$224

Fastest flight time

4h 05m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Jamaica in the past 72 hours is $224. The best round-trip flight deal from Jamaica to Chicago found on momondo in the last 72 hours is $366.
The fastest flight from Jamaica to Chicago takes 4h 05m
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

Frequently asked questions about flying from Jamaica to Chicago

  • 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
United AirlinesPriceFrom $281Free CancellationRating
7.4
9,656 reviews
Search United Airlines flights
SouthwestPriceFrom $281Free CancellationRating
8.0
4,327 reviews
Search Southwest flights
American AirlinesPriceFrom $291Free CancellationRating
7.1
11,673 reviews
Search American Airlines flights
Spirit AirlinesPriceFrom $380Free CancellationRating
6.3
8,630 reviews
Search Spirit Airlines flights
DeltaPriceFrom $451Free CancellationRating
7.9
8,459 reviews
Search Delta flights

Traveling to a place near Chicago?

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