Cheap flights from Chicago to Jamaica from $91

Round-trip
1 adult
Economy
0 bags
From?
To?
Sun 4/2
Sun 4/9

Deals available from 900+ travel sites.

Flight information for Chicago to Jamaica

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

Best Price Found

$91

Fastest flight time

3h 00m

Direct flights

Every day
The best one-way flight to Jamaica from Chicago in the past 72 hours is $91. The best round-trip flight deal from Chicago to Jamaica found on momondo in the last 72 hours is $275.
The fastest flight from Chicago to Jamaica takes 3h 00m
Direct flights go from Chicago to Jamaica every day.

How to get the cheapest flight ticket from Chicago to Jamaica

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 airline that flies to Jamaica from Chicago?

Frontier. Air Canada, American Airlines, and Frontier are the most popular carriers operating from Chicago to Jamaica

What is the cheapest Chicago to Jamaica flight route?

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

Easily compare round-trip flights from Chicago to Jamaica

Below you can see the best fares for your round-trip flight route over the next six months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Chicago to Jamaica by changing tabs
Frontier
Apr 22
ORD5:07 pmChicago O'Hare Intl
11h 32m
1 stop
MBJ4:39 amMontego Bay Sangster Intl
Apr 27
MBJ3:17 pmMontego Bay Sangster Intl
13h 53m
1 stop
ORD5:10 amChicago O'Hare Intl
$234
Find similar
Multiple Airlines
Apr 15
ORD5:07 pmChicago O'Hare Intl
11h 27m
1 stop
MBJ4:34 amMontego Bay Sangster Intl
Apr 19
MBJ12:00 pmMontego Bay Sangster Intl
22h 08m
1 stop
ORD10:08 amChicago O'Hare Intl
$291
Find similar
Spirit Airlines
Apr 30
ORD3:56 pmChicago O'Hare Intl
15h 51m
1 stop
MBJ7:47 amMontego Bay Sangster Intl
May 5
MBJ8:40 amMontego Bay Sangster Intl
9h 27m
1 stop
ORD6:07 pmChicago O'Hare Intl
$306
Find similar
American Airlines
Apr 17
ORD5:09 amChicago O'Hare Intl
3h 55m
MBJ9:04 amMontego Bay Sangster Intl
Apr 20
MBJ10:04 amMontego Bay Sangster Intl
4h 31m
ORD2:35 pmChicago O'Hare Intl
$340
Find similar
United Airlines
Apr 22
ORD1:48 amChicago O'Hare Intl
7h 37m
1 stop
MBJ9:25 amMontego Bay Sangster Intl
Apr 26
MBJ9:50 amMontego Bay Sangster Intl
4h 20m
ORD2:10 pmChicago O'Hare Intl
$344
Find similar
Delta
Sep 19
MDW9:00 amChicago Midway
6h 47m
1 stop
KIN3:47 pmKingston Norman Manley
Sep 26
KIN5:00 amKingston Norman Manley
7h 07m
1 stop
MDW12:07 pmChicago Midway
$436
Find similar

Find the cheapest one-way flights from Chicago to Jamaica

If you're looking for one-way flights from Chicago to Jamaica, view some of our deals below provided by American Airlines, Frontier and Spirit Airlines
Frontier
Apr 22
ORD5:07 pmChicago O'Hare Intl
11h 32m
1 stop
MBJ4:39 amMontego Bay Sangster Intl
$91
Find similar
Multiple Airlines
Apr 19
ORD2:46 pmChicago O'Hare Intl
42h 46m
2 stops
MBJ9:32 amMontego Bay Sangster Intl
$129
Find similar
Spirit Airlines
Apr 16
ORD3:56 pmChicago O'Hare Intl
15h 51m
1 stop
MBJ7:47 amMontego Bay Sangster Intl
$146
Find similar

Search last-minute flights to Jamaica from Chicago

Find and compare round-trip flight prices for your last-minute flight from Chicago to Jamaica
Frontier
Apr 5
MDW10:51 amChicago Midway
22h 42m
2 stops
MBJ9:33 amMontego Bay Sangster Intl
Apr 8
MBJ11:05 amMontego Bay Sangster Intl
4h 12m
MDW3:17 pmChicago Midway
$330
Find similar
American Airlines
Apr 2
ORD4:05 pmChicago O'Hare Intl
13h 36m
1 stop
MBJ5:41 amMontego Bay Sangster Intl
Apr 5
MBJ10:50 amMontego Bay Sangster Intl
17h 52m
1 stop
ORD4:42 amChicago O'Hare Intl
$424
Find similar
United Airlines
Apr 2
ORD4:45 amChicago O'Hare Intl
4h 00m
MBJ8:45 amMontego Bay Sangster Intl
Apr 5
MBJ9:50 amMontego Bay Sangster Intl
4h 20m
ORD2:10 pmChicago O'Hare Intl
$440
Find similar
Multiple Airlines
Apr 3
ORD1:05 amChicago O'Hare Intl
6h 50m
1 stop
MBJ7:55 amMontego Bay Sangster Intl
Apr 10
MBJ11:07 amMontego Bay Sangster Intl
33h 47m
2 stops
ORD8:54 pmChicago O'Hare Intl
$443
Find similar
Spirit Airlines
Apr 2
ORD3:56 pmChicago O'Hare Intl
15h 40m
1 stop
MBJ7:36 amMontego Bay Sangster Intl
Apr 5
MBJ12:00 pmMontego Bay Sangster Intl
17h 52m
2 stops
ORD5:52 amChicago O'Hare Intl
$457
Find similar
Delta
Apr 7
MDW2:00 pmChicago Midway
17h 51m
2 stops
MBJ7:51 amMontego Bay Sangster Intl
Apr 12
MBJ9:20 amMontego Bay Sangster Intl
10h 27m
1 stop
MDW7:47 pmChicago Midway
$509
Find similar

Best airlines flying from Chicago to Jamaica

Compare and see reviews for airlines that fly from Chicago to Jamaica with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $193Free CancellationRating
6.1
829 reviews
Search Frontier flights
United AirlinesPriceFrom $292Free CancellationRating
7.2
1,736 reviews
Search United Airlines flights
American AirlinesPriceFrom $292Free CancellationRating
7.2
2,055 reviews
Search American Airlines flights
Spirit AirlinesPriceFrom $323Free CancellationRating
6.3
1,880 reviews
Search Spirit Airlines flights
DeltaPriceFrom $425Free CancellationRating
7.8
824 reviews
Search Delta flights
JetBluePriceFrom $489Free CancellationRating
7.0
922 reviews
Search JetBlue flights
Air CanadaPriceFrom $597Free CancellationRating
7.3
325 reviews
Search Air Canada flights
British AirwaysPriceFrom $662Free CancellationRating
6.4
1,294 reviews
Search British Airways flights
Alaska AirlinesPriceFrom $677Free CancellationRating
7.9
1,607 reviews
Search Alaska Airlines flights

Spirit Airlines flights from Chicago to Jamaica

Our best Spirit Airlines deals on Chicago to Jamaica flight tickets
Spirit Airlines
Apr 30
ORD3:56 pmChicago O'Hare Intl
15h 51m
1 stop
MBJ7:47 amMontego Bay Sangster Intl
May 5
MBJ8:40 amMontego Bay Sangster Intl
9h 27m
1 stop
ORD6:07 pmChicago O'Hare Intl
$306
Find similar
Spirit Airlines
Apr 16
ORD3:56 pmChicago O'Hare Intl
15h 51m
1 stop
MBJ7:47 amMontego Bay Sangster Intl
Apr 19
MBJ8:55 amMontego Bay Sangster Intl
8h 57m
1 stop
ORD5:52 pmChicago O'Hare Intl
$358
Find similar
Spirit Airlines
May 1
ORD12:37 pmChicago O'Hare Intl
19h 17m
2 stops
MBJ7:54 amMontego Bay Sangster Intl
May 4
MBJ8:55 amMontego Bay Sangster Intl
19h 12m
2 stops
ORD4:07 amChicago O'Hare Intl
$363
Find similar

Frontier flights from Chicago to Jamaica

Our best Frontier deals on Chicago to Jamaica flight tickets
Frontier
Apr 22
ORD5:07 pmChicago O'Hare Intl
11h 32m
1 stop
MBJ4:39 amMontego Bay Sangster Intl
Apr 27
MBJ3:17 pmMontego Bay Sangster Intl
13h 53m
1 stop
ORD5:10 amChicago O'Hare Intl
$234
Find similar
Frontier
Apr 10
ORD5:07 pmChicago O'Hare Intl
12h 27m
1 stop
MBJ5:34 amMontego Bay Sangster Intl
Apr 13
MBJ2:09 pmMontego Bay Sangster Intl
15h 01m
1 stop
ORD5:10 amChicago O'Hare Intl
$240
Find similar
Frontier
Apr 17
ORD5:07 pmChicago O'Hare Intl
12h 27m
1 stop
MBJ5:34 amMontego Bay Sangster Intl
Apr 20
MBJ2:44 pmMontego Bay Sangster Intl
14h 26m
1 stop
ORD5:10 amChicago O'Hare Intl
$241
Find similar

Alternative routes for Chicago to Jamaica

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Chicago to Montego Bay Flights
Fastest flight time3h 55m
Cheapest price$266
St. Louis to Montego Bay Flights
Fastest flight time3h 37m
Cheapest price$291

Flights to other cities in Jamaica

Lost the lust for Jamaica? Check out some flights to other cities in Jamaica

FLIGHTS TO

Montego Bay

from$206

FLIGHTS TO

Kingston

from$240

FLIGHTS TO

Ocho Rios

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Why use momondo?

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Flights from Chicago to Jamaica with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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