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Cheap flights from Jamaica to Chicago from $153

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 2/7. 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.
Frontier Logo
2:35 pm - 10:44 pm
MBJ
-
ORD
9h 09m1 stop
Frontier Logo
6:03 am - 1:30 pm
ORD
-
MBJ
6h 27m1 stop
$304Frontier
sam., janv. 24 - sam., janv. 31
Multiple Airlines Logo
2:35 pm - 1:37 pm
MBJ
-
ORD
24h 02m1 stop
Multiple Airlines Logo
5:15 am - 12:02 pm
ORD
-
MBJ
5h 47m1 stop
$311Multiple Airlines
sam., janv. 24 - lun., janv. 26
Frontier Logo
3:47 pm - 10:24 pm
MBJ
-
ORD
7h 37m1 stop
Frontier Logo
6:05 am - 2:29 pm
ORD
-
MBJ
7h 24m1 stop
$322Frontier
jeu., déc. 25 - mer., déc. 31
Spirit Airlines Logo
1:05 pm - 12:30 am
MBJ
-
ORD
12h 25m1 stop
Spirit Airlines Logo
5:32 pm - 12:02 pm
ORD
-
MBJ
17h 30m1 stop
$330Spirit Airlines
sam., déc. 27 - sam., janv. 31
Spirit Airlines Logo
1:17 pm - 7:38 pm
KIN
-
ORD
7h 21m1 stop
Spirit Airlines Logo
5:15 am - 12:12 pm
ORD
-
KIN
5h 57m1 stop
$338Spirit Airlines
ven., janv. 23 - ven., janv. 30
American Airlines Logo
3:51 pm - 7:29 pm
MBJ
-
ORD
4h 38mnonstop
American Airlines Logo
10:11 am - 3:24 pm
ORD
-
MBJ
4h 13mnonstop
$341American Airlines
jeu., déc. 25 - mer., déc. 31
Multiple Airlines Logo
2:35 pm - 8:18 am
MBJ
-
ORD
18h 43m2 stops
Multiple Airlines Logo
5:15 am - 12:02 pm
ORD
-
MBJ
5h 47m1 stop
$342Multiple Airlines
sam., janv. 24 - lun., janv. 26
Delta Logo
8:00 am - 5:22 pm
MBJ
-
ORD
10h 22m2 stops
Delta Logo
5:30 am - 12:58 pm
ORD
-
MBJ
6h 28m1 stop
$346Delta
jeu., déc. 25 - mer., déc. 31
American Airlines Logo
5:28 pm - 11:27 pm
MBJ
-
ORD
6h 59m1 stop
American Airlines Logo
10:09 am - 3:22 pm
ORD
-
MBJ
4h 13mnonstop
$372American Airlines
sam., janv. 24 - lun., janv. 26
Delta Logo
9:00 am - 6:49 pm
KIN
-
ORD
10h 49m1 stop
Delta Logo
6:50 am - 8:00 pm
ORD
-
KIN
12h 10m2 stops
$400Delta
ven., janv. 23 - ven., janv. 30

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
Jan 24
MBJ2:35 pmMontego Bay Sangster Intl
9h 09m
1 stop
ORD10:44 pmChicago O'Hare Intl
Jan 31
ORD6:03 amChicago O'Hare Intl
6h 27m
1 stop
MBJ1:30 pmMontego Bay Sangster Intl
$304
Find similar
Frontier
Dec 25
MBJ3:47 pmMontego Bay Sangster Intl
7h 37m
1 stop
ORD10:24 pmChicago O'Hare Intl
Dec 31
ORD6:05 amChicago O'Hare Intl
7h 24m
1 stop
MBJ2:29 pmMontego Bay Sangster Intl
$322
Find similar
Frontier
Dec 23
MBJ3:47 pmMontego Bay Sangster Intl
7h 37m
1 stop
ORD10:24 pmChicago O'Hare Intl
Dec 28
ORD8:09 pmChicago O'Hare Intl
17h 20m
2 stops
MBJ2:29 pmMontego Bay Sangster Intl
$462
Find similar

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

Our best Spirit Airlines deals on Jamaica to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines
Dec 27
MBJ1:05 pmMontego Bay Sangster Intl
12h 25m
1 stop
ORD12:30 amChicago O'Hare Intl
Jan 31
ORD5:32 pmChicago O'Hare Intl
17h 30m
1 stop
MBJ12:02 pmMontego Bay Sangster Intl
$330
Find similar
Spirit Airlines
Jan 23
KIN1:17 pmKingston Norman Manley
7h 21m
1 stop
ORD7:38 pmChicago O'Hare Intl
Jan 30
ORD5:15 amChicago O'Hare Intl
5h 57m
1 stop
KIN12:12 pmKingston Norman Manley
$338
Find similar
Spirit Airlines
Dec 27
KIN1:19 pmKingston Norman Manley
12h 11m
1 stop
ORD12:30 amChicago O'Hare Intl
Jan 3
ORD5:00 amChicago O'Hare Intl
6h 14m
1 stop
KIN12:14 pmKingston Norman Manley
$388
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 décembre 10, 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

sam. 1/24

2:35 pm-10:44 pm

1 stop9h 09m

Chicago O'Hare Intl

sam. 1/31

6:03 am-1:30 pm

1 stop6h 27m

$304

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

sam. 1/24

2:35 pm-1:37 pm

1 stop24h 02m

Chicago O'Hare Intl

lun. 1/26

5:15 am-12:02 pm

1 stop5h 47m

$311

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

jeu. 12/25

3:47 pm-10:24 pm

1 stop7h 37m

Chicago O'Hare Intl

mer. 12/31

6:05 am-2:29 pm

1 stop7h 24m

$322

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

sam. 12/27

1:05 pm-12:30 am

1 stop12h 25m

Chicago O'Hare Intl

sam. 1/31

5:32 pm-12:02 pm

1 stop17h 30m

$330

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

ven. 1/23

1:17 pm-7:38 pm

1 stop7h 21m

Chicago O'Hare Intl

ven. 1/30

5:15 am-12:12 pm

1 stop5h 57m

$338

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

jeu. 12/25

3:51 pm-7:29 pm

Nonstop4h 38m

Chicago O'Hare Intl

mer. 12/31

10:11 am-3:24 pm

Nonstop4h 13m

$341

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

sam. 1/24

2:35 pm-8:18 am

2 stops18h 43m

Chicago O'Hare Intl

lun. 1/26

5:15 am-12:02 pm

1 stop5h 47m

$342

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

jeu. 12/25

8:00 am-5:22 pm

2 stops10h 22m

Chicago O'Hare Intl

mer. 12/31

5:30 am-12:58 pm

1 stop6h 28m

$346

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

sam. 1/24

5:28 pm-11:27 pm

1 stop6h 59m

Chicago O'Hare Intl

lun. 1/26

10:09 am-3:22 pm

Nonstop4h 13m

$372

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

ven. 1/23

9:00 am-6:49 pm

1 stop10h 49m

Chicago O'Hare Intl

ven. 1/30

6:50 am-8:00 pm

2 stops12h 10m

$400

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 February is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Jamaica averaging around $388.

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 $428. 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 $542.

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 $454 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 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 10% 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

$251

Fastest flight time

4h 29m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Jamaica in the past 72 hours is $251. The best round-trip flight deal from Jamaica to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $387.
The fastest flight from Jamaica to Chicago O'Hare Intl Airport takes 4h 29m
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
8,174 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $348Free CancellationRating
7.2
11,047 reviews
Search American Airlines flights
United AirlinesPriceFrom $349Free CancellationRating
7.4
9,092 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
South Haven
Schaumburg
Rockford
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Tinley Park
Janesville
Aurora
Elgin
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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