$199 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

Thu, Oct 22 - Sun, Oct 25
American Airlines Logo
12:13 pm - 11:00 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
10h 47m1 stop Charlotte Douglas
American Airlines Logo
6:55 am - 4:12 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
9h 17m1 stop Dallas/Fort Worth
$326American Airlines
Thu, Oct 22 - Sun, Oct 25
American Airlines Logo
12:13 pm - 11:36 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
11h 23m2 stops Charlotte Douglas Washington, D.C. Reagan-National
American Airlines Logo
6:00 am - 4:12 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
10h 12m1 stop Dallas/Fort Worth
$331American Airlines
Thu, Oct 22 - Sun, Oct 25
Frontier Logo
3:48 pm - 11:43 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
7h 55m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:24 am - 2:33 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
8h 09m1 stop Atlanta Hartsfield-Jackson
$368Frontier
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
$371United Airlines
Wed, Oct 21 - Mon, Oct 26
Air Canada Logo
12:30 pm - 9:00 amMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
20h 30m1 stop Toronto Pearson Intl
Air Canada Logo
8:45 am - 4:20 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
7h 35m1 stop Toronto Pearson Intl
$372Air Canada
Mon, Nov 23 - Sat, Nov 28
United Airlines Logo
2:54 pm - 6:20 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 26mnonstop
United Airlines Logo
12:01 am - 2:39 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
13h 38m1 stop Houston George Bush Intcntl
$376United Airlines
Tue, Nov 3 - Fri, Nov 13
Southwest Logo
1:50 pm - 10:40 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
9h 50m2 stops Orlando Nashville Intl
Southwest Logo
8:40 pm - 2:05 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
16h 25m2 stops Orlando Baltimore/Washington
$476Southwest
Tue, Nov 3 - Fri, Nov 13
Southwest Logo
1:00 pm - 9:25 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
9h 25m1 stop Baltimore/Washington
Southwest Logo
8:40 pm - 2:05 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
16h 25m2 stops Orlando Baltimore/Washington
$476Southwest
Tue, Nov 10 - Mon, Nov 16
JetBlue Logo
5:02 pm - 11:55 pmKIN  Kingston Norman Manley-ORD Chicago O'Hare Intl
7h 53m1 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
Sun, Nov 1 - Sun, Dec 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 - 6:28 pmORD  Chicago O'Hare Intl-KIN Kingston Norman Manley
10h 28m1 stop Fort Lauderdale
$1,452JetBlue
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 December, where tickets cost $300 on average for return flights. On the other hand, the most expensive months are August and July, where the average cost of tickets from Jamaica is $605 and $488 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 $460.

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 $540 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 $133.

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Good to know

Cheapest flight

$199
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 $544. The cheapest price found on KAYAK in the last 2 weeks cost $230 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.

  • How many direct flights to Chicago are there each week?

    Each week there are around 30,034 direct flights from within Jamaica to Chicago. The most common day for departures is Sunday, with 16% of flights taking off on this day.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $295 or less one-way and $540 or less round-trip.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

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
Schererville
Chesterton
Munster
Porter
Monticello
Saint John
Griffith

More options for your flight to Chicago