$204 Find Cheap Flights from Jamaica to Chicago - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Jamaica to Chicago

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Jamaica to Chicago

Sun, Sep 20 - Sun, Oct 4
Frontier Logo
3:42 pm - 11:44 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 02m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:25 am - 2:27 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
8h 02m1 stop Atlanta Hartsfield-Jackson
$324Frontier
Mon, Nov 2 - Fri, Nov 13
Air Canada Logo
1:50 pm - 9:23 amMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
20h 33m1 stop Toronto Pearson Intl
Air Canada Logo
8:50 pm - 5:20 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
19h 30m1 stop Toronto Pearson Intl
$348Air Canada
Mon, Nov 2 - Fri, Nov 13
American Airlines Logo
3:57 pm - 7:46 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 49mnonstop
American Airlines Logo
9:40 am - 2:57 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
4h 17mnonstop
$411American Airlines
Fri, Sep 4 - Mon, Sep 7
American Airlines Logo
2:12 pm - 6:55 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 43mnonstop
American Airlines Logo
9:00 am - 1:12 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
4h 12mnonstop
$411American Airlines
Mon, Nov 23 - Sun, Nov 29
United Airlines Logo
2:54 pm - 6:20 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 26mnonstop
United Airlines Logo
8:40 am - 1:48 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
4h 08mnonstop
$411United Airlines
Sat, Sep 12 - Sat, Sep 19
United Airlines Logo
2:40 pm - 12:59 amMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
10h 19m1 stop Houston George Bush Intcntl
United Airlines Logo
7:05 am - 11:43 amORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
28h 38m1 stop Newark
$421United Airlines
Sat, Sep 19 - Tue, Oct 6
Southwest Logo
1:25 pm - 8:35 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
7h 10m1 stop Baltimore/Washington
Southwest Logo
5:45 am - 11:50 amMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
6h 05m1 stop Orlando
$426Southwest
Fri, Oct 16 - Mon, Oct 19
JetBlue Logo
1:53 pm - 11:44 pmKIN  Kingston Norman Manley-ORD Chicago O'Hare Intl
9h 51m1 stop Fort Lauderdale
JetBlue Logo
7:00 am - 12:43 pmORD  Chicago O'Hare Intl-KIN Kingston Norman Manley
5h 43m1 stop Fort Lauderdale
$446JetBlue
Thu, Sep 17 - Sat, Sep 26
Southwest Logo
2:15 pm - 10:45 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 30m1 stop Orlando
Southwest Logo
5:55 am - 12:25 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
6h 30m1 stop Baltimore/Washington
$449Southwest
Wed, Sep 30 - Mon, Oct 5
JetBlue Logo
3:05 pm - 11:08 pmKIN  Kingston Norman Manley-ORD Chicago O'Hare Intl
8h 03m1 stop Fort Lauderdale
JetBlue Logo
6:00 am - 12:45 pmORD  Chicago O'Hare Intl-KIN Kingston Norman Manley
6h 45m1 stop Fort Lauderdale
$492JetBlue
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 the cheapest day to fly to Chicago?

Based on KAYAK data, the cheapest day to fly to Chicago is Wednesday where round-trip tickets can be as cheap as $398. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $531 on average.

What is the cheapest month to fly to Chicago?

The cheapest month for flights to Chicago is September, where tickets cost $348 on average for return flights. On the other hand, the most expensive months are October and August, where the average cost of tickets from Jamaica is $539 and $536 respectively. For one-way flights, the best month to travel is December with an average price of $229.

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

The cheapest time of day to fly to Chicago is generally in the evening, when round-trip flights cost $454 on average. The most expensive time of day to fly to Chicago is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $467.

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 $411 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 (RFD), with an average flight price of $120.

Good to know

Cheapest flight

$204
Most popular time to fly and prices are also 20% lower on average.
Flight from Montego Bay to Chicago Midway 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 $539. The cheapest price found on KAYAK in the last 2 weeks cost $238 and departed from Montego Bay Sangster Intl Airport.

  • 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.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $363 or less one-way and $411 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 airline flying from Jamaica to Chicago

 
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.
7.1
American AirlinesOverall score based on 11974 reviews
7.5Boarding
6.8Entertainment
6.4Food
7.9Crew
7.2Comfort
Airline reviews

We landed slightly early but then sat in holding area waiting for our gate to clear out for about an hour, so technically we arrived one hour late at the gate at ORD. The airport may be partially responsible here, but regardless of who is responsible, it was a bad experience to be so close yet unable to get off the plane.

6.0 GoodAnonymous, Aug 2026
Read more American Airlines reviews

We landed slightly early but then sat in holding area waiting for our gate to clear out for about an hour, so technically we arrived one hour late at the gate at ORD. The airport may be partially responsible here, but regardless of who is responsible, it was a bad experience to be so close yet unable to get off the plane.

Delays and cancellations. Mechanics weren’t on site. Replacement plane took hours to arrive although it should have arrived within 90 minutes. Flight back was cancelled. Ended up driving over 12 hours and wasting 3 days between everything.

Little bit of trouble getting my KTN and pre-check status onto the ticket, but otherwise the counter staff were friendly and truly concerned to get it right.

The flight could have actually taken place. Canceled flight and no option to rebook that day.

Missed connection from delays and times changing multiple times and then involuntarily booked on another airline next day

The flight was delayed in 30 minute increments for a total of 4 hours and 30 minute delay. All other flights to Chicago left on time except for this one flight. If there is an issue with the inbound flight, just let customers know so they can find another flight right away, Once we got on the plane there was another 30 minute delay taking off at 10:30 at night which is very unusual that a flight wouldn't be ready to take off

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

Take this flight regularly. Every single week same thing. Departure delayed. Make up some time in the air. Land at ORD and then wait for gate in "L" concourse Terminal 3 for 30-40 min-which yields a very delayed final arrival. Plus I get to taxi around and see every runway and drive over the bridge (IFKYK) over the expressway 2-4 times in most cases. Change the sched of incoming plane/work with FAA to improve traffic flow at ORD/change the timing of these flights. Whatever it takes. But do better.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Boarding and Delays The boarding process for my American Airlines flight from Copenhagen to Philadelphia was a bit tricky. We experienced a gate change that required a long walk to a new area of the airport. Additionally, boarding was not via a jet bridge; we had to take a shuttle bus to the plane and then carry our luggage up the stairs ourselves. Furthermore, the bag drop didn't open until about 12:20 PM, which was only three hours before our scheduled departure. This meant I couldn't drop my bag off early and had to wait outside of security in order to drop off my bag and use the kiosk. The bag drop self-service kiosks also didn't open until about 12:00 PM when an American Airlines employee unlocked them so that we could print out our boarding passes and bag tags, which further created a backlog. The flight was delayed by over an hour because we had to wait for one of the tires on the plane to be changed. Flight Attendant Professionalism On a positive note, the flight attendant was very professional when handling a passenger who was sitting in the wrong seat. Even though the passenger was persistent and reluctant to move, the flight attendant calmly ensured the assigned passenger could take their seat. Kudos to the flight attendant for keeping his calm and composure, not allowing the issue to escalate, and handling it well under pressure while a line of passengers waited in the aisle to board. In-Flight Service The in-flight service was also fast, prompt, and efficient, although service had to be suspended for the last two hours of the flight due to weather and turbulence, which was outside of the crew's control. Limited Flight Options Please note that American Airlines only operates one flight per day in and out of Copenhagen. This means there are limited options available if your flight is delayed or canceled, which is something to take into consideration when booking.

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
Munster
Schererville
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago