$158 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 5/20. 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
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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

Sat, May 9 - Mon, May 18
Frontier Logo
1:16 pm - 7:55 am
MBJ
-
ORD
18h 39m
1 stop
Frontier Logo
6:55 am - 12:11 pm
ORD
-
MBJ
29h 16m
1 stop
$263Frontier
Tue, Apr 28 - Tue, May 12
Spirit Airlines Logo
1:21 pm - 12:24 am
MBJ
-
ORD
11h 03m
1 stop
Spirit Airlines Logo
5:05 am - 12:16 pm
ORD
-
MBJ
7h 11m
1 stop
$278Spirit Airlines
Fri, Jun 5 - Sun, Aug 23
American Airlines Logo
2:30 pm - 7:15 pm
MBJ
-
ORD
4h 45mnonstop
American Airlines Logo
8:30 am - 12:31 pm
ORD
-
MBJ
4h 01mnonstop
$281American Airlines
Fri, May 8 - Fri, May 15
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
American Airlines Logo
5:00 am - 1:25 pm
ORD
-
MBJ
8h 25m
1 stop
$286American Airlines
Sat, May 16 - Mon, May 18
United Airlines Logo
2:40 pm - 9:00 am
MBJ
-
ORD
18h 20m
1 stop
United Airlines Logo
9:56 pm - 1:30 pm
ORD
-
MBJ
15h 34m
1 stop
$291United Airlines
Sat, May 9 - Sat, May 23
United Airlines Logo
4:12 pm - 4:30 pm
MBJ
-
ORD
24h 18m
1 stop
United Airlines Logo
9:40 pm - 3:10 pm
ORD
-
MBJ
17h 30m
1 stop
$292United Airlines
Mon, May 4 - Wed, May 13
Multiple Airlines Logo
3:18 pm - 11:55 pm
KIN
-
ORD
8h 37m
1 stop
Multiple Airlines Logo
5:05 am - 2:12 pm
ORD
-
KIN
9h 07m
1 stop
$404Multiple Airlines
Sat, May 9 - Tue, Sep 1
Southwest Logo
11:35 am - 3:45 pm
MBJ
-
MDW
4h 10mnonstop
Southwest Logo
6:15 am - 11:55 am
MDW
-
MBJ
5h 40m
1 stop
$406Southwest
Sat, Apr 18 - Sat, Apr 25
Multiple Airlines Logo
1:17 pm - 10:14 pm
MBJ
-
MDW
8h 57m
1 stop
Multiple Airlines Logo
7:34 pm - 12:16 pm
MDW
-
MBJ
16h 42m
2 stops
$439Multiple Airlines
Mon, May 4 - Mon, May 11
Southwest Logo
12:15 pm - 10:45 pm
MBJ
-
MDW
10h 30m
2 stops
Southwest Logo
7:30 am - 1:55 pm
MDW
-
MBJ
6h 25m
1 stop
$499Southwest
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 flight to Chicago?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

In the last 3 days, the cheapest flight deal to Chicago was found on the route from Montego Bay, at $263 return. The most popular connection is from Los Angeles to Chicago and KAYAK users have found round-trip deals for as low as $176 in the last 3 days.

What is the cheapest day to fly to Chicago?

The average price of all round-trip flights to Chicago clicked on KAYAK for each day over the last 12 months.

Based on KAYAK data, the cheapest day to fly to Chicago is Wednesday where round-trip tickets can be as cheap as $419. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $640 on average.

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

The average price for all round-trip flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

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 $487.

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 $301 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 $151.

Good to know

Low seasonMarch
Cheapest flight$158
Best time to beat the crowds but there is an average 57% increase in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Montego Bay to Chicago Midway Airport

FAQs - booking Chicago flights

  • What is the cheapest flight to Chicago?

    In the last 3 days, the cheapest flight deal to Chicago was found on the route from Montego Bay, at $263 return. The most popular connection is from Los Angeles to Chicago and KAYAK users have found round-trip deals for as low as $176 in the last 3 days.

  • 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 $333. The cheapest price found on KAYAK in the last 2 weeks cost $172 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 $218 or less one-way and $301 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

 
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.
7.1
American AirlinesOverall score based on 11488 reviews
7.2Comfort
7.9Crew
7.5Boarding
6.4Food
6.9Entertainment
Airline reviews

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

8.0 ExcellentSonia, Mar 2026
BOS - ORD
Read more American Airlines reviews

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

I understand that there is a catering issue - water should be the minimum stock. During the flight, not once that the attendants came through with water. The conversations in the kitchen were very loud and they were swearing. I do not expect any white glove service, at the minimum, we should be cordial. It was almost an inconveniece that we were on the flight. And it made us feel if you even dare question us, we'll make you deplane.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

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.