$194 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 10/27. 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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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, Jul 9 - Sat, Aug 29
American Airlines Logo
2:36 pm - 7:27 pm
MBJ
-
ORD
4h 51mnonstop
American Airlines Logo
9:10 am - 1:17 pm
ORD
-
MBJ
4h 07mnonstop
$301American Airlines
Wed, May 20 - Tue, May 26
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
American Airlines Logo
5:00 am - 1:54 pm
ORD
-
MBJ
8h 54m
1 stop
$306American Airlines
Sat, May 16 - Mon, May 18
American Airlines Logo
3:20 pm - 11:58 pm
MBJ
-
ORD
8h 38m
1 stop
American Airlines Logo
8:05 am - 12:13 pm
ORD
-
MBJ
4h 08mnonstop
$312American Airlines
Sat, May 16 - Fri, May 29
United Airlines Logo
4:12 pm - 7:26 am
MBJ
-
ORD
15h 14m
1 stop
United Airlines Logo
9:55 pm - 3:10 pm
ORD
-
MBJ
17h 15m
1 stop
$316United Airlines
Wed, Aug 12 - Thu, Aug 20
Frontier Logo
1:32 pm - 7:53 am
MBJ
-
ORD
18h 21m
1 stop
Frontier Logo
6:55 am - 12:21 pm
ORD
-
MBJ
29h 26m
1 stop
$382Frontier
Thu, May 28 - Fri, Jul 10
Frontier Logo
1:16 pm - 7:55 am
MBJ
-
ORD
18h 39m
1 stop
Frontier Logo
8:05 pm - 9:12 am
ORD
-
MBJ
13h 07m
1 stop
$388Frontier
Wed, Jun 17 - Wed, Jun 24
Air Canada Logo
3:05 pm - 8:00 am
KIN
-
ORD
16h 55m
1 stop
Air Canada Logo
8:40 pm - 10:25 am
ORD
-
KIN
13h 45m
1 stop
$527Air Canada
Wed, Jun 17 - Wed, Jun 24
Air Canada Logo
3:05 pm - 7:45 am
KIN
-
ORD
16h 40m
2 stops
Air Canada Logo
8:40 pm - 10:25 am
ORD
-
KIN
13h 45m
1 stop
$529Air Canada
Mon, May 25 - Tue, Sep 1
Delta Logo
9:00 am - 9:53 pm
KIN
-
ORD
12h 53m
1 stop
Delta Logo
8:55 am - 8:04 pm
ORD
-
KIN
11h 09m
2 stops
$531Delta
Thu, Jul 9 - Fri, Jul 10
Delta Logo
9:00 am - 5:12 pm
KIN
-
ORD
8h 12m
1 stop
Delta Logo
7:17 pm - 8:03 pm
ORD
-
KIN
24h 46m
2 stops
$539Delta
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 flight to Chicago O'Hare Airport?

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 O'Hare Airport was found on the route from Montego Bay, at $301 return. The most popular connection is from New York to Chicago O'Hare Airport and KAYAK users have found round-trip deals for as low as $160 in the last 3 days.

What is the cheapest day to fly to Chicago?

The average price of all round-trip flights to Chicago O'Hare Intl Airport 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 $410. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $531 on average.

What is the cheapest time of day to fly to Chicago O'Hare Intl Airport?

The average price for all round-trip flights to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport is generally in the evening, when round-trip 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 $461.

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 $316 round-trip.

Good to know

Low seasonJanuary
Cheapest flight$194
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Montego Bay to Chicago O'Hare Airport

FAQs - booking Chicago O'Hare Airport flights

  • What is the cheapest flight to Chicago O'Hare Airport?

    In the last 3 days, the cheapest flight deal to Chicago O'Hare Airport was found on the route from Montego Bay, at $301 return. The most popular connection is from New York to Chicago O'Hare Airport and KAYAK users have found round-trip deals for as low as $160 in the last 3 days.

  • 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 $337. The cheapest price found on KAYAK in the last 2 weeks cost $182 and departed from Montego Bay Sangster Intl Airport.

  • 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.

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 $270
  • 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 airlines flying 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 9684 reviews
7.1Entertainment
8.1Crew
7.7Boarding
6.6Food
7.3Comfort
Airline reviews

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

6.0 GoodAnonymous, May 2026
DEN - ORD
Read more United Airlines reviews

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Didn't make it back on American Airlines due to a maintenance issue. The communication and updates were terrible. I ended up returning on Aero Mexico which had a much nicer aircraft with a large entertainment screen with movies and shows AND they had a nice inflight meal. That was a treat after being delayed 26 hours! I think some additional flight miles, or something should be offered for that long of a delay ---it was not pleasant at all---very physical and emotional experience.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

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
Hammond
Des Plaines
Hoffman Estates
Portage
Willowbrook
South Holland
Delavan
Northbrook
Lansing
Lisle
Pleasant Prairie
Elmhurst
Valparaiso

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

Information on the airport you'll fly into in Chicago