$204 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 12/17. 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

Fri, Oct 16 - Mon, Oct 19
Delta Logo
1:32 pm - 8:20 pm
MBJ
-
ORD
6h 48m
1 stop
Delta Logo
7:10 am - 1:20 pm
ORD
-
MBJ
6h 10m
1 stop
$317Delta
Mon, Nov 23 - Sun, Nov 29
United Airlines Logo
2:48 pm - 6:16 pm
MBJ
-
ORD
4h 28mnonstop
United Airlines Logo
8:42 am - 1:46 pm
ORD
-
MBJ
4h 04mnonstop
$321United Airlines
Sat, Aug 29 - Sat, Sep 5
American Airlines Logo
2:12 pm - 6:55 pm
MBJ
-
ORD
4h 43mnonstop
American Airlines Logo
5:00 am - 4:08 pm
ORD
-
MBJ
11h 08m
1 stop
$326American Airlines
Sat, Jul 4 - Mon, Aug 31
American Airlines Logo
3:02 pm - 11:30 pm
MBJ
-
ORD
8h 28m
1 stop
American Airlines Logo
9:00 am - 1:12 pm
ORD
-
MBJ
4h 12mnonstop
$332American Airlines
Sat, Jul 4 - Mon, Aug 31
American Airlines Logo
3:02 pm - 12:41 am
MBJ
-
ORD
9h 39m
1 stop
American Airlines Logo
8:49 pm - 2:23 pm
ORD
-
MBJ
17h 34m
1 stop
$336American Airlines
Mon, Sep 7 - Mon, Sep 28
American Airlines Logo
5:08 pm - 7:34 am
MBJ
-
ORD
14h 26m
1 stop
American Airlines Logo
5:20 am - 12:53 pm
ORD
-
MBJ
7h 33m
2 stops
$341American Airlines
Thu, Aug 13 - Mon, Aug 17
American Airlines Logo
2:12 pm - 6:55 pm
MBJ
-
ORD
4h 43mnonstop
American Airlines Logo
9:00 am - 1:12 pm
ORD
-
MBJ
4h 12mnonstop
$399American Airlines
Tue, Jul 14 - Mon, Aug 24
Copa Airlines Logo
12:22 pm - 4:00 am
MBJ
-
ORD
15h 38m
1 stop
Copa Airlines Logo
3:21 pm - 11:15 am
ORD
-
MBJ
19h 54m
1 stop
$436Copa Airlines
Sat, Jul 18 - Sat, Jul 25
JetBlue Logo
12:08 pm - 11:44 pm
KIN
-
ORD
11h 36m
1 stop
JetBlue Logo
7:00 am - 5:18 pm
ORD
-
KIN
10h 18m
1 stop
$478JetBlue
Wed, Jul 15 - Sat, Jul 25
JetBlue Logo
12:08 pm - 11:44 pm
KIN
-
ORD
11h 36m
1 stop
JetBlue Logo
2:35 pm - 9:17 pm
ORD
-
KIN
6h 42m
1 stop
$516JetBlue
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 5 days.

In the last 5 days, the cheapest flight deal to Chicago O'Hare Airport was found on the route from Montego Bay, at $317 return. The most popular connection is from Kingston to Chicago O'Hare Airport and KAYAK users have found round-trip deals for as low as $430 in the last 5 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 Thursday where round-trip tickets can be as cheap as $386. On the other hand, the most expensive day to fly is Friday, where round-trip prices are $537 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 afternoon, 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 evening, which is peak travel time and where the average cost of a ticket is $454.

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 $301 round-trip.

Good to know

Low seasonSeptember
Cheapest flight$204
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 16% 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 5 days, the cheapest flight deal to Chicago O'Hare Airport was found on the route from Montego Bay, at $317 return. The most popular connection is from Kingston to Chicago O'Hare Airport and KAYAK users have found round-trip deals for as low as $430 in the last 5 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 $430. The cheapest price found on KAYAK in the last 2 weeks cost $198 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 $287
  • 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 9868 reviews
7.3Comfort
6.6Food
8.1Crew
7.1Entertainment
7.7Boarding
Airline reviews

Very easy ! Use the kiosk and bag drop and right to security within 10 min

10.0 ExcellentJoanne, Jun 2026
DEN - ORD
Read more United Airlines reviews

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

I flew from Barcelona to Chicago on UA yesterday. The flight was on time, the pilots did a great job and the flight attendants were super nice. All of them. Also food was good, and the drinks, including wine were served a few times during our flight. I highly recommend this airline.

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

The clerk at check in for my bags was very rude. My credit card was hacked during my vacation and she told me it was not possible to pay in cash for my bag. “You bought the cheapest ticket, you should have bought a ticket that included a bag. If you cannot pay with a credit card, we will not let you on this flight”. She spoke to her supervisor and then told me , I could ask other passengers, if they would use their credit card to check my bag. I had to beg 5 different people, till one agreed to use their credit card. I payed them cash of course. This was a very stressful and humiliating experience for me. I strongly suggest you build in some kind of provision for travelers who got robbed.

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.

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

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
Hammond
Elk Grove Village
Des Plaines
Hoffman Estates
Portage
South Holland
Willowbrook
Delavan
Lansing
Northbrook
Lisle
Elmhurst
Alsip
Pleasant Prairie

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

Information on the airport you'll fly into in Chicago