$151 Find Cheap Flights from Jamaica to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 3/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$231
Spirit Airlines
Thu 3/5Wed 3/11
MBJ - ORD • 1 stop
Cheapest non-stop
$295
United Airlines
Thu 3/5Wed 3/11
MBJ - ORD • Non-stop
Top airlines
American Airlines
Most flights • 12 per week
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Jamaica to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Jamaica to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Jamaica to Chicago

Thu, Mar 5 - Wed, Mar 11
Spirit Airlines Logo
1:00 pm - 7:11 pm
MBJ
-
ORD
7h 11m
1 stop
Spirit Airlines Logo
5:15 am - 11:02 am
ORD
-
MBJ
5h 47m
1 stop
$231Spirit Airlines
Thu, Mar 5 - Wed, Mar 11
Spirit Airlines Logo
1:00 pm - 11:47 pm
MBJ
-
ORD
11h 47m
1 stop
Spirit Airlines Logo
5:15 am - 11:02 am
ORD
-
MBJ
5h 47m
1 stop
$248Spirit Airlines
Thu, Mar 5 - Wed, Mar 11
United Airlines Logo
2:48 pm - 6:13 pm
MBJ
-
ORD
4h 25mnonstop
United Airlines Logo
8:42 am - 12:46 pm
ORD
-
MBJ
4h 04mnonstop
$295United Airlines
Thu, Mar 5 - Wed, Mar 11
United Airlines Logo
2:48 pm - 6:13 pm
MBJ
-
ORD
4h 25mnonstop
United Airlines Logo
9:15 pm - 1:05 pm
ORD
-
MBJ
15h 50m
1 stop
$298United Airlines
Thu, May 14 - Sun, May 17
Delta Logo
4:55 pm - 7:58 am
MBJ
-
ORD
15h 03m
2 stops
Delta Logo
7:05 am - 3:29 pm
ORD
-
MBJ
8h 24m
1 stop
$307Delta
Thu, Mar 5 - Wed, Mar 11
Delta Logo
12:20 pm - 5:45 pm
MBJ
-
MDW
6h 25m
1 stop
Delta Logo
6:00 am - 3:28 pm
MDW
-
MBJ
9h 28m
1 stop
$307Delta
Fri, May 15 - Tue, May 19
Multiple Airlines Logo
12:00 pm - 10:57 pm
KIN
-
ORD
10h 57m
1 stop
Multiple Airlines Logo
1:27 pm - 11:05 am
ORD
-
KIN
21h 38m
1 stop
$359Multiple Airlines
Mon, Mar 30 - Mon, Apr 6
American Airlines Logo
3:04 pm - 8:38 am
MBJ
-
ORD
17h 34m
1 stop
American Airlines Logo
8:05 am - 12:11 pm
ORD
-
MBJ
4h 06mnonstop
$381American Airlines
Mon, Mar 30 - Mon, Apr 6
American Airlines Logo
3:04 pm - 8:38 am
MBJ
-
ORD
17h 34m
1 stop
American Airlines Logo
6:59 pm - 11:51 am
ORD
-
MBJ
16h 52m
1 stop
$385American Airlines
Tue, May 19 - Mon, Aug 31
Multiple Airlines Logo
12:00 pm - 9:17 pm
KIN
-
ORD
9h 17m
1 stop
Multiple Airlines Logo
5:15 am - 11:05 am
ORD
-
KIN
29h 50m
1 stop
$387Multiple Airlines
Booking Insights

KAYAK's insights & trends for flights to Chicago

Get data-powered insights and trends for flights to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is a good deal for flights to Chicago?

If you’re looking for cheap airfare to Chicago, 25% of our users found tickets to Chicago for the following prices or less: From Montego Bay $290 one-way - $363 round-trip.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Greater Rockford Airport, with an average flight price of $134.

Good to know

Low seasonMarch
Cheapest flight$151
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Montego Bay to Chicago O'Hare Airport

FAQs - booking Chicago flights

  • Which Chicago airport is closest to central Chicago?

    9 miles away from Chicago’s city center, Chicago Midway Airport is the closest of the 3 major airports in the city. There are 16 miles separating Chicago city center to Chicago O'Hare Airport, and 79 miles to Chicago Greater Rockford.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $384. The cheapest price found on KAYAK in the last 2 weeks cost $249 and departed from Montego Bay Sangster Intl Airport.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Wednesday where tickets can be as cheap as $438. On the other hand, the most expensive day to fly is Monday, where prices are $640 on average.

  • How does KAYAK find such low prices on flights to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Chicago?

    The cheapest time of day to fly to Chicago is generally in the afternoon, when flights cost $498 on average. The most expensive time of day to fly to Chicago is generally in the evening, which is peak travel time and where the average cost of a ticket is $507.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $290 or less one-way and $363 or less round-trip.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the top airlines flying from Jamaica to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Jamaica to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8138 reviews
7.2Food
8.5Crew
7.9Comfort
8.1Boarding
7.8Entertainment
Airline reviews

I didn't take this flight. I changed the flight. Why am I getting surveys and notifications on flights that I change. Seems like a defect with Kayak.

2.0 MediocreTodd, Jan 2026
IAH - ATL
Read more Delta reviews

I didn't take this flight. I changed the flight. Why am I getting surveys and notifications on flights that I change. Seems like a defect with Kayak.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Very convenient considering that is a non-stop flight, but the Aeromexico still has old model planes, so the entertainment was very poor and the space for carry-on luggage was very limited.

Flight from CHI to PVD was delayed by over 20 hours.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Griffith
Saint John

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.