$153 Find Cheap Flights from Jamaica to Chicago O'Hare Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to O'Hare Intl departing on 2/7. 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 O'Hare Intl Airport

 
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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Everything you should know

Cheapest round-trip
$246
Overall average: $566
Spirit Airlines
Thu 1/15Thu 1/22
MBJ - ORD • 1 stop
Cheapest non-stop
$362
Typical prices: $491-$641
American Airlines
Thu 1/15Thu 1/22
MBJ - ORD • Non-stop
When to travel
September
Cheapest • 27% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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We hope you love your trip to O'Hare Intl!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Jamaica to O'Hare Intl

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Jamaica to O'Hare Intl 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 O'Hare Intl

Thu, Jan 15 - Thu, Jan 22
Spirit Airlines Logo
12:57 pm - 7:38 pm
MBJ
-
ORD
7h 41m1 stop
Spirit Airlines Logo
8:43 pm - 12:02 pm
ORD
-
MBJ
14h 19m1 stop
$246Spirit Airlines
Sat, Jan 31 - Sat, Feb 7
Frontier Logo
2:35 pm - 10:44 pm
MBJ
-
ORD
9h 09m1 stop
Frontier Logo
6:03 am - 1:30 pm
ORD
-
MBJ
6h 27m1 stop
$304Frontier
Thu, Jan 15 - Thu, Jan 22
Multiple Airlines Logo
12:57 pm - 10:44 pm
MBJ
-
ORD
10h 47m2 stops
Multiple Airlines Logo
8:43 pm - 12:02 pm
ORD
-
MBJ
14h 19m1 stop
$321Multiple Airlines
Sat, Jan 31 - Sat, Feb 7
Multiple Airlines Logo
2:35 pm - 8:18 am
MBJ
-
ORD
18h 43m2 stops
Multiple Airlines Logo
5:15 am - 12:02 pm
ORD
-
MBJ
5h 47m1 stop
$342Multiple Airlines
Fri, Jan 30 - Fri, Feb 6
Spirit Airlines Logo
1:17 pm - 11:22 am
KIN
-
ORD
23h 05m1 stop
Spirit Airlines Logo
5:15 am - 12:12 pm
ORD
-
KIN
5h 57m1 stop
$349Spirit Airlines
Thu, Jan 15 - Thu, Jan 22
American Airlines Logo
3:12 pm - 6:51 pm
MBJ
-
ORD
4h 39mnonstop
American Airlines Logo
10:09 am - 3:22 pm
ORD
-
MBJ
4h 13mnonstop
$362American Airlines
Thu, Jan 15 - Thu, Jan 22
American Airlines Logo
3:12 pm - 6:51 pm
MBJ
-
ORD
4h 39mnonstop
American Airlines Logo
7:56 pm - 11:33 am
ORD
-
MBJ
14h 37m1 stop
$367American Airlines
Fri, Jan 30 - Fri, Feb 6
Delta Logo
9:00 am - 6:45 pm
KIN
-
ORD
10h 45m2 stops
Delta Logo
6:50 am - 8:00 pm
ORD
-
KIN
12h 10m2 stops
$400Delta
Thu, Jan 22 - Mon, Jan 26
Air Canada Logo
2:55 pm - 3:10 pm
KIN
-
ORD
25h 15m1 stop
Air Canada Logo
1:55 pm - 1:45 pm
ORD
-
KIN
46h 50m2 stops
$470Air Canada
Thu, Jan 15 - Thu, Jan 22
Air Canada Logo
1:30 pm - 8:10 pm
MBJ
-
ORD
31h 40m2 stops
Air Canada Logo
6:00 pm - 12:30 pm
ORD
-
MBJ
17h 30m2 stops
$526Air Canada
Booking Insights

KAYAK's insights & trends for flights to O'Hare Intl

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

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights to Chicago O'Hare Intl Airport is September, where tickets cost $348 on average for one-way flights. On the other hand, the most expensive months are January and April, where the average cost of tickets from Jamaica is $566 and $542 respectively. For return trips, the best month to travel is September with an average price of $348.

What is a good deal for flights to Chicago O'Hare Intl Airport?

If you’re looking for cheap airfare to Chicago O'Hare Intl Airport, 25% of our users found tickets to Chicago O'Hare Intl Airport for the following prices or less: From Montego Bay $237 one-way - $414 round-trip.

Good to know

Low seasonJanuary
Cheapest flight$153
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 15% lower on average.
Flight from Montego Bay to Chicago O'Hare Airport

FAQs - booking Chicago O'Hare Airport flights

  • How far is Chicago O'Hare Intl Airport from central Chicago?

    The distance between Chicago O'Hare Intl Airport and downtown Chicago is 16 miles.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $345. The cheapest price found on KAYAK in the last 2 weeks cost $212 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 $434. On the other hand, the most expensive day to fly is Monday, where prices are $542 on average.

  • How does KAYAK find such low prices on flights to Chicago O'Hare Airport?

    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 O'Hare Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport 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 O'Hare Airport?

    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 O'Hare Airport 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 O'Hare Airport?

    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 O'Hare Airport 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 O'Hare Intl Airport?

    The cheapest time of day to fly to Chicago O'Hare Intl Airport is generally in the evening, when flights cost $454 on average. The most expensive time of day to fly to Chicago O'Hare Intl Airport is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $492.

Top tips for finding cheap flights to Chicago O'Hare Airport

  • Looking for cheap airfare to Chicago O'Hare Airport? 25% of our users found round-trip tickets to Chicago O'Hare Airport for the following prices or less: From Montego Bay $325
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago O'Hare Airport flight deals.

Reviews of the top 3 airlines serving from Jamaica to O'Hare Intl

 
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 O'Hare Intl? 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.
7.4
United AirlinesOverall score based on 9092 reviews
7.7Boarding
6.6Food
8.1Crew
7.1Entertainment
7.3Comfort
Airline reviews

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

10.0 ExcellentRoger, Dec 2025
CAE - ORD
Read more United Airlines reviews

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

United has come a long way, it’s been a fantastic experience traveling with them.

This flight leg was fantastic - super comfortable and a great selection of things to watch on the TV. Staff were excellent, really above and beyond.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Excellent all round, first time flying United. App is very helpful.

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.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Flight, food and crew were all good, friendly and very satisfactory.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Premium economy seat was decent. As always poor headphones, poor food and beverage, crew is not overly friendly

Excellent - explanations were clear staff was nice and flight was comfortable

Seats Are hard, Plane was very dirty, used gum stuck on my tray table, wet red liquid under my feet at me seat

Flight was on time. Friendly crew. Gate agents in the other hand were very unfriendly.

Bought round trip tickets. Ended up upgrading to first class. Both flights were new planes but hadn’t been equipped with WiFi and there were no charging ports at my seat despite it being new and first class accommodations.

Like: seats that don't move; fast boarding; engaging crew; low-prices; individual gate at LGA; access to restrooms at the gate Dislike: no water on the flight

To be Honest they canceled my flight and didn't have other options. Until 4 says later and I have a 2yr old very disappointed.

The whole thing everything was poorly managed poorly handled spirit doent deserve to be in business period.

Nothing. It was delayed three times and then canceled and we had to drive 15 hours to get home and rent a car.

Excellent experience when I am looking for a budget airline where the main expectation is getting me from point A to point B with no frills.

Had to deplane for undisclosed mechanical issue. Landed in Chicago 3 hours late. Food voucher at FLL came just as we were recording. Crew and agents were troopers--better than Spirit last night.

I don’t like the idea of having to buy everything including a bottle of water when the other airlines are giving it to us

Traveling to a place near O'Hare Intl?

Book flights to O'Hare Intl if you plan to visit one of these locations
Gurnee
South Haven
Merrillville
Oak Brook
Saint Joseph
Tinley Park
Elk Grove Village
Des Plaines
Hoffman Estates
Hammond
Willowbrook
Portage
Delavan
Northbrook
South Holland
Pleasant Prairie
Lansing
Elmhurst
Valparaiso
Lisle

Everything you need to know for your flight to O'Hare Intl

Information on the airport you'll fly into in Chicago