Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Jamaica to Chicago from $178

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 4/30. 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

Enter your travel dates to find the best prices.
Spirit Airlines Logo
1:21 pm - 12:27 am
MBJ
-
ORD
11h 06m
1 stop
Spirit Airlines Logo
5:05 am - 12:16 pm
ORD
-
MBJ
7h 11m
1 stop
$270Spirit Airlines
Thu, May 7 - Tue, May 12
Spirit Airlines Logo
1:21 pm - 12:24 am
MBJ
-
ORD
11h 03m
1 stop
Spirit Airlines Logo
5:05 am - 12:16 pm
ORD
-
MBJ
7h 11m
1 stop
$278Spirit Airlines
Tue, Apr 28 - Tue, May 12
United Airlines Logo
1:52 pm - 6:15 pm
MBJ
-
ORD
4h 23mnonstop
United Airlines Logo
5:30 am - 1:30 pm
ORD
-
MBJ
8h 00m
1 stop
$286United Airlines
Sat, May 16 - Tue, May 19
United Airlines Logo
2:40 pm - 9:00 am
MBJ
-
ORD
18h 20m
1 stop
United Airlines Logo
9:56 pm - 1:30 pm
ORD
-
MBJ
15h 34m
1 stop
$291United Airlines
Sat, May 16 - Mon, May 18
United Airlines Logo
4:12 pm - 8:47 am
MBJ
-
ORD
16h 35m
1 stop
United Airlines Logo
5:30 am - 1:30 pm
ORD
-
MBJ
8h 00m
1 stop
$292United Airlines
Sat, May 16 - Tue, May 19
American Airlines Logo
10:17 am - 5:58 pm
MBJ
-
ORD
7h 41m
1 stop
American Airlines Logo
9:20 am - 1:30 pm
ORD
-
MBJ
4h 10mnonstop
$297American Airlines
Wed, May 13 - Wed, May 27
American Airlines Logo
3:20 pm - 11:34 pm
MBJ
-
ORD
8h 14m
1 stop
American Airlines Logo
6:35 pm - 9:10 am
ORD
-
MBJ
14h 35m
1 stop
$301American Airlines
Sun, May 17 - Sat, Sep 12
Air Canada Logo
3:05 pm - 9:05 am
KIN
-
ORD
18h 00m
1 stop
Air Canada Logo
8:20 pm - 1:55 pm
ORD
-
KIN
17h 35m
1 stop
$443Air Canada
Fri, May 22 - Tue, May 26
Air Canada Logo
3:05 pm - 9:05 am
KIN
-
ORD
18h 00m
1 stop
Air Canada Logo
8:20 pm - 1:55 pm
ORD
-
KIN
17h 35m
1 stop
$446Air Canada
Wed, May 13 - Tue, May 26
Multiple Airlines Logo
3:18 pm - 11:59 pm
KIN
-
ORD
8h 41m
1 stop
Multiple Airlines Logo
7:45 pm - 2:12 pm
ORD
-
KIN
18h 27m
1 stop
$467Multiple Airlines
Fri, May 15 - Tue, May 19

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
May 2
MBJ1:17 pmMontego Bay Sangster Intl
9h 22m
1 stop
ORD10:39 pmChicago O'Hare Intl
May 9
ORD7:52 pmChicago O'Hare Intl
16h 19m
2 stops
MBJ12:11 pmMontego Bay Sangster Intl
$381
Frontier
May 2
MBJ1:17 pmMontego Bay Sangster Intl
20h 28m
2 stops
ORD9:45 amChicago O'Hare Intl
May 9
ORD7:52 pmChicago O'Hare Intl
16h 19m
2 stops
MBJ12:11 pmMontego Bay Sangster Intl
$438

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
May 7
MBJ1:21 pmMontego Bay Sangster Intl
11h 06m
1 stop
ORD12:27 amChicago O'Hare Intl
May 12
ORD5:05 amChicago O'Hare Intl
7h 11m
1 stop
MBJ12:16 pmMontego Bay Sangster Intl
$270
Spirit Airlines
Apr 28
MBJ1:21 pmMontego Bay Sangster Intl
11h 03m
1 stop
ORD12:24 amChicago O'Hare Intl
May 12
ORD5:05 amChicago O'Hare Intl
7h 11m
1 stop
MBJ12:16 pmMontego Bay Sangster Intl
$278
Spirit Airlines
May 12
MBJ1:21 pmMontego Bay Sangster Intl
11h 06m
1 stop
ORD12:27 amChicago O'Hare Intl
May 13
ORD7:45 pmChicago O'Hare Intl
16h 31m
1 stop
MBJ12:16 pmMontego Bay Sangster Intl
$307

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 March 19, 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 5/7

1:21 pm-12:27 am

1 stop11h 06m

Chicago O'Hare Intl

Tue 5/12

5:05 am-12:16 pm

1 stop7h 11m

$270

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 4/28

1:21 pm-12:24 am

1 stop11h 03m

Chicago O'Hare Intl

Tue 5/12

5:05 am-12:16 pm

1 stop7h 11m

$278

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 5/16

1:52 pm-6:15 pm

Nonstop4h 23m

Chicago O'Hare Intl

Tue 5/19

5:30 am-1:30 pm

1 stop8h 00m

$286

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 5/16

2:40 pm-9:00 am

1 stop18h 20m

Chicago O'Hare Intl

Mon 5/18

9:56 pm-1:30 pm

1 stop15h 34m

$291

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 5/16

4:12 pm-8:47 am

1 stop16h 35m

Chicago O'Hare Intl

Tue 5/19

5:30 am-1:30 pm

1 stop8h 00m

$292
Quickest round-trip

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 5/13

10:17 am-5:58 pm

1 stop7h 41m

Chicago O'Hare Intl

Wed 5/27

9:20 am-1:30 pm

Nonstop4h 10m

$297

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sun 5/17

3:20 pm-11:34 pm

1 stop8h 14m

Chicago O'Hare Intl

Sat 9/12

6:35 pm-9:10 am

1 stop14h 35m

$301

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Fri 5/22

3:05 pm-9:05 am

1 stop18h 00m

Chicago O'Hare Intl

Tue 5/26

8:20 pm-1:55 pm

1 stop17h 35m

$443

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 5/13

3:05 pm-9:05 am

1 stop18h 00m

Chicago O'Hare Intl

Tue 5/26

8:20 pm-1:55 pm

1 stop17h 35m

$446

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Fri 5/15

3:18 pm-11:59 pm

1 stop8h 41m

Chicago O'Hare Intl

Tue 5/19

7:45 pm-2:12 pm

1 stop18h 27m

$467

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 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 $419. 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 $633.

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 $484. 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.

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

$192

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 $192. The best round-trip flight deal from Jamaica to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $301.
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

  • 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 $146Free CancellationRating
6.3
8,528 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $305Free CancellationRating
7.1
11,475 reviews
Search American Airlines flights
United AirlinesPriceFrom $306Free CancellationRating
7.4
9,441 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
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Rosemont
Naperville
New Buffalo
Orland Park
Kenosha
Oak Brook
Joliet
Racine
Janesville
Hammond
Aurora
Tinley Park
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.

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
Sat 4/18
Sat 4/25
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago