$170 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 5/9. 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

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
Tue, May 12 - Wed, May 13
Spirit Airlines Logo
1:21 pm - 12:27 am
MBJ
-
ORD
11h 06m
1 stop
Spirit Airlines Logo
7:45 pm - 12:16 pm
ORD
-
MBJ
16h 31m
1 stop
$294Spirit 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
Mon, May 4 - Wed, May 13
Air Canada Logo
3:05 pm - 12:17 pm
KIN
-
ORD
21h 12m
2 stops
Air Canada Logo
8:20 pm - 10:25 am
ORD
-
KIN
14h 05m
1 stop
$418Air Canada
Fri, May 22 - Tue, May 26
Air Canada Logo
3:05 pm - 9:05 am
KIN
-
ORD
18h 00m
1 stop
Air Canada Logo
8:20 pm - 1:55 pm
ORD
-
KIN
17h 35m
1 stop
$423Air 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 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 $263 return. The most popular connection is from Boston to Chicago O'Hare Airport and KAYAK users have found round-trip deals for as low as $140 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 $419. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $633 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 $484.

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 seasonJanuary
Cheapest flight$170
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 20% 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 $263 return. The most popular connection is from Boston to Chicago O'Hare Airport and KAYAK users have found round-trip deals for as low as $140 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 $315. 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 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 $249
  • 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 9451 reviews
7.3Comfort
7.1Entertainment
8.1Crew
7.7Boarding
6.6Food
Airline reviews

Economy plus was so cramped I could not use my laptop. It was beyond bad.

4.0 OkayBryan, Mar 2026
MCO - ORD
Read more United Airlines reviews

Economy plus was so cramped I could not use my laptop. It was beyond bad.

Would've been great if Lufthansa union cockpit pilots didn't strike for 2 days and caused a chaos to my returning plans to USA, and then after rebooking a flight 2 days later tge plane departed 35 min later. So I did not have a good experience.

They never clean the toilet, and the food is worse

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Chargers didn’t work, no entertainment and we had to wait for taxiing for easily 40 minutes after arriving early. Bags were late too!

No real complaints. The in flight food was much better than I expected. The in flight entertainment was excellent.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Horrible Flight significantly delayed. Not due to united issue. But trying to rebook connection flight and get information about overnight accommodation was difficult. Agent did not seem to care or have any interest to help.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

This Japanese airline provides great service and very helpful in assisting their passengers.

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.

Delayed 11 hours with two being on our destinations tarmac, no compensation or refund and was told I would actually get charged a $200 cancellation fee if I decided to switch airlines for my return flight. For their inconvenience they gave a $10 meal voucher to split between two people in a airport.

Like Spirit but bad that you have to pay for water 🙃

If there are delays, it takes less than a minute for a Spirit employee to make an announcement. It’s very simple.

For a change, friendly staff at check-in and in flight.

Delayed both in takeoff and landing, trash plane no amenities, I've said it before but I'll never fly Spirit again.

It’s was a cheap flight and they got us there safely. It’s just their whole business model that make the experience “meh.” They make you paranoid about whether your personal item is too big. They make you paranoid about being crammed into a middle seat at the back of the plane. They purposely cram people together leaving multiple rows completely empty and even after the door closes the FA’s announce that everyone has to sit in their assigned seat. We knew what we were buying and in that regard we got a cheap and safe flight but it felt like they do their best to take any enjoyment out of the experience. That’s all on management, not the crew.

Had to pay for my bag a mini weekender bag 100 dollar fee

The flight was delayed for unknown reasons while other airlines weren’t. It was very frustrating.

Everything was good. On time, boarding fast, flight attendants friendly.

Spirit has always and will always stink. Absolute worst airline around.

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
Willowbrook
Portage
South Holland
Delavan
Northbrook
Lansing
Pleasant Prairie
Lisle
Elmhurst
Valparaiso

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

Information on the airport you'll fly into in Chicago