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

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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

Mon, Nov 23 - Sun, Nov 29
Air Canada Logo
6:20 pm - 9:23 amMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
16h 03m1 stop Toronto Pearson Intl
Air Canada Logo
4:30 pm - 5:20 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
23h 50m1 stop Toronto Pearson Intl
$357Air Canada
Mon, Nov 23 - Sun, Nov 29
Air Canada Logo
6:20 pm - 11:07 amMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
17h 47m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
4:30 pm - 5:20 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
23h 50m1 stop Toronto Pearson Intl
$360Air Canada
Wed, Dec 2 - Thu, Dec 31
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
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
Wed, Dec 2 - Thu, Dec 31
American Airlines Logo
6:09 pm - 12:44 amMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
7h 35m1 stop Miami
American Airlines Logo
9:17 am - 2:30 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
4h 13mnonstop
$412American Airlines
Sat, Sep 19 - Tue, Oct 6
American Airlines Logo
12:17 pm - 10:35 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
10h 18m1 stop Philadelphia
American Airlines Logo
6:29 am - 1:08 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
6h 39m1 stop Charlotte Douglas
$416American Airlines
Thu, Oct 22 - Sun, Oct 25
Southwest Logo
12:50 pm - 10:00 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
9h 10m1 stop Baltimore/Washington
Southwest Logo
9:20 pm - 11:50 amMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
14h 30m2 stops Baltimore/Washington Orlando
$491Southwest
Sat, Sep 12 - Sat, Sep 19
Southwest Logo
11:40 am - 8:35 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 55m1 stop Baltimore/Washington
Southwest Logo
5:00 am - 12:50 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
7h 50m1 stop Orlando
$538Southwest
Mon, Nov 2 - Fri, Nov 13
JetBlue Logo
5:02 pm - 11:57 pmKIN  Kingston Norman Manley-ORD Chicago O'Hare Intl
7h 55m1 stop Fort Lauderdale
JetBlue Logo
7:00 am - 1:48 pmORD  Chicago O'Hare Intl-KIN Kingston Norman Manley
5h 48m1 stop Fort Lauderdale
$560JetBlue
Fri, Sep 11 - Sat, Sep 12
JetBlue Logo
1:40 pm - 11:08 pmKIN  Kingston Norman Manley-ORD Chicago O'Hare Intl
9h 28m1 stop Fort Lauderdale
JetBlue Logo
6:00 am - 12:45 pmORD  Chicago O'Hare Intl-KIN Kingston Norman Manley
6h 45m1 stop Fort Lauderdale
$1,404JetBlue
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 $413. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $547 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 August and October, where the average cost of tickets from Jamaica is $605 and $539 respectively. For one-way flights, the best month to travel is December with an average price of $232.

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 $463.

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 $416 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 $116.

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Good to know

Cheapest flight

$204
Most popular time to fly and prices are also 21% 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 $567. The cheapest price found on KAYAK in the last 2 weeks cost $243 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 $440 or less one-way and $416 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 12023 reviews
7.5Boarding
6.8Entertainment
6.4Food
7.2Comfort
7.9Crew
Airline reviews

Mostly excellent. However, many too many gate changes. Connecting flight at ORD changed gate 6 times.

10.0 ExcellentPeter, Aug 2026
Read more American Airlines reviews

Mostly excellent. However, many too many gate changes. Connecting flight at ORD changed gate 6 times.

Mechanical issues and delays. I get it but bad experience. Turned my 3 hour airport experience into a 9 hours

The baggage process at the gate was terrible. Stay was not friendly at all

Flight was delayed because of mechanical. Could not get landing space which caused me to miss my connection. Messy and not organized.

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

Traveling to a place near Chicago?

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

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago

First Class flights to Chicago
Business Class flights to Chicago
Premium Economy Class flights to Chicagofrom $1,268
Economy Class flights to Chicagofrom $243