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Cheap flights from Chicago to Jamaica from $99

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Jamaica departing on 5/14. 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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Sun 4/28
Sun 5/5

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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
May 5
ORD6:00 amChicago O'Hare Intl
7h 59m
1 stop
MBJ1:59 pmMontego Bay Sangster Intl
May 11
MBJ8:32 amMontego Bay Sangster Intl
8h 55m
1 stop
ORD5:27 pmChicago O'Hare Intl
Multiple Airlines
May 11
ORD6:00 amChicago O'Hare Intl
9h 19m
1 stop
MBJ3:19 pmMontego Bay Sangster Intl
May 17
MBJ12:45 pmMontego Bay Sangster Intl
10h 44m
1 stop
ORD11:29 pmChicago O'Hare Intl
Spirit Airlines
May 12
ORD5:00 amChicago O'Hare Intl
6h 41m
1 stop
MBJ11:41 amMontego Bay Sangster Intl
May 17
MBJ12:45 pmMontego Bay Sangster Intl
10h 44m
1 stop
ORD11:29 pmChicago O'Hare Intl
American Airlines
Jul 7
ORD8:45 amChicago O'Hare Intl
3h 55m
MBJ12:40 pmMontego Bay Sangster Intl
Jul 11
MBJ2:05 pmMontego Bay Sangster Intl
4h 30m
ORD6:35 pmChicago O'Hare Intl
United Airlines
Aug 1
ORD9:15 pmChicago O'Hare Intl
16h 10m
1 stop
MBJ1:25 pmMontego Bay Sangster Intl
Aug 4
MBJ1:51 pmMontego Bay Sangster Intl
4h 24m
ORD6:15 pmChicago O'Hare Intl
Delta
Sep 7
MDW5:59 pmChicago Midway
17h 23m
2 stops
MBJ11:22 amMontego Bay Sangster Intl
Sep 12
MBJ4:25 pmMontego Bay Sangster Intl
16h 20m
2 stops
MDW8:45 amChicago Midway

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
May 14
ORD6:00 amChicago O'Hare Intl
8h 53m
1 stop
MBJ2:53 pmMontego Bay Sangster Intl
Spirit Airlines
May 7
ORD10:00 pmChicago O'Hare Intl
13h 41m
2 stops
MBJ11:41 amMontego Bay Sangster Intl
Multiple Airlines
May 3
ORD10:00 pmChicago O'Hare Intl
9h 20m
1 stop
MBJ7:20 amMontego Bay Sangster Intl

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
May 2
MDW10:17 pmChicago Midway
9h 03m
1 stop
MBJ7:20 amMontego Bay Sangster Intl
May 4
MBJ11:51 amMontego Bay Sangster Intl
10h 50m
1 stop
MDW10:41 pmChicago Midway
Spirit Airlines
May 3
ORD10:00 pmChicago O'Hare Intl
13h 45m
2 stops
MBJ11:45 amMontego Bay Sangster Intl
May 10
MBJ12:45 pmMontego Bay Sangster Intl
24h 40m
3 stops
ORD1:25 pmChicago O'Hare Intl
Multiple Airlines
May 2
ORD10:00 pmChicago O'Hare Intl
14h 09m
2 stops
MBJ12:09 pmMontego Bay Sangster Intl
May 6
MBJ3:34 pmMontego Bay Sangster Intl
25h 53m
1 stop
ORD5:27 pmChicago O'Hare Intl
American Airlines
Apr 28
ORD8:55 amChicago O'Hare Intl
4h 05m
MBJ1:00 pmMontego Bay Sangster Intl
May 1
MBJ2:00 pmMontego Bay Sangster Intl
4h 35m
ORD6:35 pmChicago O'Hare Intl
United Airlines
May 2
ORD9:37 pmChicago O'Hare Intl
15h 48m
1 stop
MBJ1:25 pmMontego Bay Sangster Intl
May 4
MBJ1:51 pmMontego Bay Sangster Intl
4h 24m
ORD6:15 pmChicago O'Hare Intl
Delta
Apr 28
ORD7:30 pmChicago O'Hare Intl
17h 40m
2 stops
MBJ1:10 pmMontego Bay Sangster Intl
May 1
MBJ2:35 pmMontego Bay Sangster Intl
17h 05m
2 stops
ORD7:40 amChicago O'Hare Intl

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
Spirit AirlinesPriceFrom $196Free CancellationRating
6.4
8,761 reviews
Search Spirit Airlines flights
FrontierPriceFrom $226Free CancellationRating
6.3
4,142 reviews
Search Frontier flights
United AirlinesPriceFrom $255Free CancellationRating
7.4
11,272 reviews
Search United Airlines flights
DeltaPriceFrom $324Free CancellationRating
8.0
11,028 reviews
Search Delta flights
American AirlinesPriceFrom $368Free CancellationRating
7.3
14,914 reviews
Search American Airlines flights
British AirwaysPriceFrom $434Free CancellationRating
6.8
6,927 reviews
Search British Airways flights
Air CanadaPriceFrom $560Free CancellationRating
7.0
6,859 reviews
Search Air Canada flights
Alaska AirlinesPriceFrom $594Free CancellationRating
8.1
9,111 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
May 12
ORD5:00 amChicago O'Hare Intl
6h 41m
1 stop
MBJ11:41 amMontego Bay Sangster Intl
May 17
MBJ12:45 pmMontego Bay Sangster Intl
10h 44m
1 stop
ORD11:29 pmChicago O'Hare Intl
Spirit Airlines
May 20
ORD5:00 amChicago O'Hare Intl
6h 41m
1 stop
MBJ11:41 amMontego Bay Sangster Intl
May 24
MBJ12:45 pmMontego Bay Sangster Intl
21h 10m
1 stop
ORD9:55 amChicago O'Hare Intl
Spirit Airlines
May 26
ORD5:00 amChicago O'Hare Intl
6h 41m
1 stop
MBJ11:41 amMontego Bay Sangster Intl
Jun 1
MBJ12:45 pmMontego Bay Sangster Intl
10h 44m
1 stop
ORD11:29 pmChicago O'Hare Intl

Delta flights from Chicago to Jamaica

Our best Delta deals on Chicago to Jamaica flight tickets
Delta
Sep 7
MDW5:59 pmChicago Midway
17h 23m
2 stops
MBJ11:22 amMontego Bay Sangster Intl
Sep 12
MBJ4:25 pmMontego Bay Sangster Intl
16h 20m
2 stops
MDW8:45 amChicago Midway
Delta
Jun 1
MDW6:00 amChicago Midway
13h 56m
1 stop
KIN7:56 pmKingston Norman Manley
Jun 16
KIN9:10 amKingston Norman Manley
8h 49m
1 stop
MDW5:59 pmChicago Midway
Delta
Jun 1
MDW9:32 amChicago Midway
10h 24m
2 stops
KIN7:56 pmKingston Norman Manley
Jun 16
KIN9:10 amKingston Norman Manley
8h 49m
1 stop
MDW5:59 pmChicago Midway

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. Alaska Airlines, British Airways, and Delta are the most popular carriers operating from Chicago to Jamaica

What is the cheapest Chicago to Jamaica flight route?

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

Can stopping save me money on Chicago to Jamaica flights?

You could potentially save up to 40% on your flight if you consider stops on a Chicago to Jamaica flight.

Cheap Chicago to Jamaica flight deals and tips

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

Best Price Found

$99

Fastest flight time

3h 55m

Direct flights

Every day

Airports in Jamaica

2 airports
The best one-way flight to Jamaica from Chicago in the past 72 hours is $99. The best round-trip flight deal from Chicago to Jamaica found on momondo in the last 72 hours is $235.
The fastest flight from Chicago to Jamaica takes 3h 55m
Direct flights go from Chicago to Jamaica every day.
There are 2 airports near Jamaica: Kingston Norman Manley (KIN), Montego Bay Sangster Intl (MBJ)

  • When did momondo last update prices for flights from Chicago to Jamaica?

    Prices for flights from Chicago to Jamaica refresh daily.

  • How many operators does momondo search for flights from Chicago to Jamaica?

  • How old do you have to be to fly from Chicago to Jamaica?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Jamaica.

  • What documentation or ID do you need to fly to Jamaica?

    The necessary travel and health documents for your Jamaica trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.


Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Jamaica?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Jamaica. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Jamaica with flexible booking policies on momondo?

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.

How can momondo help me find flights from Chicago to Jamaica?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Jamaica.

I’m not ready to book a flight from Chicago to Jamaica right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Jamaica from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.


An easier way to manage your Jamaica trip

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Sun 5/5
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