Cheap flights from Chicago O'Hare Intl Airport to Jamaica from $159
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago O'Hare Intl Airport to Jamaica departing on 11/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Fly from
Fly to
Route
Depart
Return
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Sun 1/17
8:59 pm-12:03 pm
1 stop14h 04m
Montego Bay Sangster Intl
Wed 1/20
4:18 pm-7:58 pm
Nonstop4h 40m
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Thu 10/29
10:26 am-2:08 pm
1 stop27h 42m
Montego Bay Sangster Intl
Sun 11/1
2:20 pm-6:30 pm
2 stops29h 10m
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Thu 11/19
7:31 am-12:56 pm
1 stop28h 25m
Montego Bay Sangster Intl
Mon 11/23
6:20 pm-7:54 am
1 stop14h 34m
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Sun 1/24
10:05 am-3:18 pm
Nonstop4h 13m
Montego Bay Sangster Intl
Fri 1/29
1:21 pm-10:30 pm
1 stop10h 09m
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Sun 11/15
8:40 am-1:48 pm
Nonstop4h 08m
Montego Bay Sangster Intl
Sat 11/21
2:54 pm-6:20 pm
Nonstop4h 26m
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Mon 11/30
8:40 am-1:48 pm
Nonstop4h 08m
Montego Bay Sangster Intl
Wed 12/9
2:54 pm-6:20 pm
Nonstop4h 26m
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Mon 11/30
7:00 am-4:18 pm
1 stop8h 18m
Montego Bay Sangster Intl
Thu 12/10
2:45 pm-11:33 pm
1 stop9h 48m
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Mon 11/30
7:00 am-4:18 pm
1 stop8h 18m
Montego Bay Sangster Intl
Wed 12/9
2:45 pm-11:33 pm
1 stop9h 48m
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Tue 10/27
5:27 am-11:51 am
1 stop6h 24m
Montego Bay Sangster Intl
Thu 10/29
1:16 pm-11:57 pm
1 stop10h 41m
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Mon 11/9
6:49 am-4:57 pm
1 stop9h 08m
Montego Bay Sangster Intl
Fri 11/13
2:16 pm-11:54 pm
1 stop10h 38m
See travel insights to Jamaica from
How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to Jamaica
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Jamaica?
The cheapest month to fly to Jamaica from Chicago O'Hare Intl Airport is in April. Flight prices, which tend to average around $458, are often lower during this time because this is during the off-season. If you aren’t able to travel to Jamaica during the month of April, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $466.
What is the cheapest day to depart on your flight to Jamaica?
The cheapest day to depart on your flight to Jamaica is on a Tuesday when prices can be found for as low as $479. This is often the case because there is less demand to fly during this day of the week. On the other hand, Saturday is the most expensive day to depart from Chicago O'Hare Intl Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $603.
What is the cheapest Chicago O'Hare Intl to Jamaica flight route?
Fly from Chicago O'Hare Intl to Montego Bay Sangster Intl for the best Chicago O'Hare Intl - Jamaica flight prices
How far in advance should I book a flight from Chicago O'Hare Intl Airport to Jamaica?
You are more likely to see cheaper flights to Jamaica from Chicago O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Jamaica for around $550 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Jamaica from Chicago O'Hare Intl Airport for as low as $493 on momondo.
What cabin class options are available on Chicago O'Hare Intl Airport to Jamaica flights?
There are 3 cabin classes available to choose from on Chicago O'Hare Intl Airport to Jamaica flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Chicago O'Hare Intl Airport to Jamaica flights?
No. A direct flight is the cheapest option for a flight between Chicago O'Hare Intl Airport to Jamaica.
What is the cheapest airline that flies from Chicago O'Hare Intl to Jamaica?
JetBlue, United Airlines, and Delta are the most popular carriers operating from Chicago O'Hare Intl to Jamaica
What airlines fly to Jamaica?
American Airlines, United Airlines and JetBlue are the top three most popular airlines that fly to Jamaica from Chicago O'Hare Intl Airport according to our data. American Airlines is the first choice among our users, with 66% of people opting to fly with this airline when traveling to Jamaica. Keep in mind that there are 4 different airlines that fly to Jamaica on a routine basis, so you have a few additional options to choose from.
Cheap Chicago O'Hare Intl Airport to Jamaica flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Jamaica
Frequently asked questions about flying from Chicago O'Hare Intl Airport to Jamaica
When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Jamaica?
Prices for flights from Chicago O'Hare Intl Airport to Jamaica are updated daily.
How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Jamaica?
There are 4 operators available for flights from Chicago O'Hare Intl Airport to Jamaica as of October 2026.
How old do you have to be to fly from Chicago O'Hare Intl Airport to Jamaica?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago O'Hare Intl Airport to Jamaica.
What documentation or ID do you need to fly to Jamaica?
The necessary travel and health documents for your Jamaica trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago O'Hare Intl Airport to Jamaica?
Based on momondo bookings for flights between Chicago O'Hare Intl Airport and Jamaica, the leading plane model is Boeing 737-800, making up 88.37% of the total bookings. Other popular models include Boeing 737 MAX 9 with 5.19%, Boeing 737 with 2.68%, and Boeing 737 MAX 8 with 1.79%.
Best airlines flying from Chicago O'Hare Intl Airport to Jamaica
Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Jamaica with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $158 | Free Cancellation | Rating 7.8 8,628 reviews | |||
| PriceFrom $301 | Free Cancellation | Rating 7.1 3,040 reviews | |||
| PriceFrom $302 | Free Cancellation | Rating 7.4 10,283 reviews | |||
| PriceFrom $314 | Free Cancellation | Rating 7.0 12,126 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Jamaica?
It is quick and easy to find Chicago to Jamaica flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Jamaica that suits you.
Can I find flights from Chicago to Jamaica with flexible booking policies on momondo?
Flights from Chicago to Jamaica with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Chicago to Jamaica?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Jamaica from Chicago.
I’m not ready to book a flight from Chicago to Jamaica right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Jamaica, momondo offers a useful price alert feature which will track prices for flights to Jamaica from Chicago and alert you when they change.