Latest deals
Insights
FAQs
Reviews
Price Alerts

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 10/8. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Jamaica to Chicago

Recent round-trip flight deals from Jamaica to Chicago

Spirit Airlines Logo
12:10 pm - 10:48 pmMBJ-ORD
10h 38m1 stop
Spirit Airlines Logo
5:05 am - 11:00 amORD-MBJ
5h 55m1 stop
$234Spirit Airlines
Find Deal
Thu, Oct 2 - Sun, Oct 5
Spirit Airlines Logo
1:12 pm - 9:00 pmMBJ-ORD
8h 48m1 stop
Spirit Airlines Logo
5:05 am - 12:05 pmORD-MBJ
6h 00m1 stop
$305Spirit Airlines
Find Deal
Fri, Nov 14 - Fri, Dec 5
American Airlines Logo
2:04 pm - 5:40 pmMBJ-ORD
4h 36mnonstop
American Airlines Logo
10:15 am - 3:22 pmORD-MBJ
4h 07mnonstop
$340American Airlines
Find Deal
Fri, Nov 14 - Fri, Dec 5
American Airlines Logo
2:04 pm - 5:40 pmMBJ-ORD
4h 36mnonstop
American Airlines Logo
8:50 pm - 12:01 pmORD-MBJ
14h 11m1 stop
$344American Airlines
Find Deal
Fri, Nov 14 - Fri, Dec 5
Frontier Logo
4:53 pm - 12:08 amMBJ-ORD
8h 15m1 stop
Frontier Logo
5:10 am - 3:33 pmORD-MBJ
9h 23m1 stop
$346Frontier
Find Deal
Thu, Dec 11 - Mon, Dec 15
United Airlines Logo
3:36 pm - 11:32 pmMBJ-ORD
8h 56m1 stop
United Airlines Logo
8:42 am - 1:46 pmORD-MBJ
4h 04mnonstop
$350United Airlines
Find Deal
Wed, Dec 10 - Mon, Dec 15
Delta Logo
5:59 pm - 12:01 amMBJ-ORD
7h 02m1 stop
Delta Logo
10:00 am - 8:36 pmORD-MBJ
9h 36m1 stop
$377Delta
Find Deal
Fri, Dec 12 - Fri, Jan 2
Delta Logo
9:00 am - 11:58 pmKIN-ORD
14h 58m1 stop
Delta Logo
9:42 am - 8:00 pmORD-KIN
10h 18m1 stop
$388Delta
Find Deal
Wed, Oct 15 - Wed, Oct 22
United Airlines Logo
2:48 pm - 6:13 pmMBJ-ORD
4h 25mnonstop
United Airlines Logo
8:42 am - 1:46 pmORD-MBJ
4h 04mnonstop
$415United Airlines
Find Deal
Wed, Dec 10 - Tue, Dec 16
Frontier Logo
11:17 am - 11:28 pmMBJ-ORD
13h 11m2 stops
Frontier Logo
5:10 am - 3:33 pmORD-MBJ
9h 23m1 stop
$418Frontier
Find Deal
Thu, Dec 11 - Mon, Dec 15

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 14
MBJ2:04 pmMontego Bay Sangster Intl
4h 36m
ORD5:40 pmChicago O'Hare Intl
Dec 5
ORD10:15 amChicago O'Hare Intl
4h 07m
MBJ3:22 pmMontego Bay Sangster Intl
$340
Find similar
American Airlines
Nov 14
MBJ2:04 pmMontego Bay Sangster Intl
4h 36m
ORD5:40 pmChicago O'Hare Intl
Dec 5
ORD8:50 pmChicago O'Hare Intl
14h 11m
1 stop
MBJ12:01 pmMontego Bay Sangster Intl
$344
Find similar
American Airlines
Dec 12
MBJ3:12 pmMontego Bay Sangster Intl
4h 47m
ORD6:59 pmChicago O'Hare Intl
Jan 2
ORD9:58 amChicago O'Hare Intl
4h 13m
MBJ3:11 pmMontego Bay Sangster Intl
$372
Find similar

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
Dec 12
MBJ5:59 pmMontego Bay Sangster Intl
7h 02m
1 stop
ORD12:01 amChicago O'Hare Intl
Jan 2
ORD10:00 amChicago O'Hare Intl
9h 36m
1 stop
MBJ8:36 pmMontego Bay Sangster Intl
$377
Find similar
Delta
Oct 15
KIN9:00 amKingston Norman Manley
14h 58m
1 stop
ORD11:58 pmChicago O'Hare Intl
Oct 22
ORD9:42 amChicago O'Hare Intl
10h 18m
1 stop
KIN8:00 pmKingston Norman Manley
$388
Find similar
Delta
Oct 8
KIN9:00 amKingston Norman Manley
7h 41m
1 stop
ORD4:41 pmChicago O'Hare Intl
Oct 15
ORD6:45 amChicago O'Hare Intl
13h 15m
1 stop
KIN8:00 pmKingston Norman Manley
$433
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 September 19, 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

Thu 10/2

12:10 pm-10:48 pm

1 stop10h 38m

Chicago O'Hare Intl

Sun 10/5

5:05 am-11:00 am

1 stop5h 55m

$234

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 11/14

1:12 pm-9:00 pm

1 stop8h 48m

Chicago O'Hare Intl

Fri 12/5

5:05 am-12:05 pm

1 stop6h 00m

$305

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 11/14

2:04 pm-5:40 pm

Nonstop4h 36m

Chicago O'Hare Intl

Fri 12/5

10:15 am-3:22 pm

Nonstop4h 07m

$340

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 11/14

2:04 pm-5:40 pm

Nonstop4h 36m

Chicago O'Hare Intl

Fri 12/5

8:50 pm-12:01 pm

1 stop14h 11m

$344

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 12/11

4:53 pm-12:08 am

1 stop8h 15m

Chicago O'Hare Intl

Mon 12/15

5:10 am-3:33 pm

1 stop9h 23m

$346

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 12/10

3:36 pm-11:32 pm

1 stop8h 56m

Chicago O'Hare Intl

Mon 12/15

8:42 am-1:46 pm

Nonstop4h 04m

$350

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 12/12

5:59 pm-12:01 am

1 stop7h 02m

Chicago O'Hare Intl

Fri 1/2

10:00 am-8:36 pm

1 stop9h 36m

$377

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 10/15

9:00 am-11:58 pm

1 stop14h 58m

Chicago O'Hare Intl

Wed 10/22

9:42 am-8:00 pm

1 stop10h 18m

$388

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 12/10

2:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

Tue 12/16

8:42 am-1:46 pm

Nonstop4h 04m

$415

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 12/11

11:17 am-11:28 pm

2 stops13h 11m

Chicago O'Hare Intl

Mon 12/15

5:10 am-3:33 pm

1 stop9h 23m

$418

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $408.

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 Saturday 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, 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 $445 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $500. 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 4 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?

No. A direct flight is the cheapest option for a flight between Jamaica to Chicago O'Hare Intl Airport.

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

$292

Fastest flight time

4h 22m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Jamaica in the past 72 hours is $292. The best round-trip flight deal from Jamaica to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $496.
The fastest flight from Jamaica to Chicago O'Hare Intl Airport takes 4h 22m
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 $251Free CancellationRating
6.3
8,030 reviews
Search Spirit Airlines flights
DeltaPriceFrom $322Free CancellationRating
7.9
7,964 reviews
Search Delta flights
American AirlinesPriceFrom $348Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $409Free CancellationRating
7.4
8,926 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
Rockford
Schaumburg
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Orland Park
Tinley Park
Elgin
Aurora
Janesville
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.

An easier way to manage your Chicago O'Hare Intl Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sun 10/19
Sun 10/26
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago