Cheap flights from Chicago to Jamaica from $158
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 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 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
Tue 11/17
5:00 am-2:14 pm
1 stop8h 14m
Montego Bay Sangster Intl
Sun 11/22
3:45 pm-12:45 am
1 stop10h 00m
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Wed 10/28
5:00 am-1:14 pm
1 stop8h 14m
Montego Bay Sangster Intl
Sun 11/1
3:45 pm-12:45 am
1 stop10h 00m
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Fri 11/13
6:00 pm-12:30 pm
1 stop17h 30m
Montego Bay Sangster Intl
Wed 11/18
6:12 pm-10:25 am
1 stop17h 13m
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-8:00 am
2 stops14h 40m
ChicagoMontego Bay
ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl
ORDMBJ
Chicago O'Hare Intl
Sat 11/7
5:29 pm-12:30 pm
2 stops18h 01m
Montego Bay Sangster Intl
Wed 11/18
6:12 pm-7:49 am
2 stops14h 37m
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Mon 11/9
6:08 am-3:08 pm
1 stop8h 00m
Montego Bay Sangster Intl
Mon 11/16
4:23 pm-11:47 pm
1 stop8h 24m
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Thu 11/5
6:42 pm-3:08 pm
1 stop19h 26m
Montego Bay Sangster Intl
Sun 11/8
4:43 pm-5:47 pm
1 stop26h 04m
See travel insights to Jamaica from
How to get the cheapest flight ticket from Chicago 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 is in April. Flight prices, which tend to average around $475, 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 $517.
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 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 to Jamaica flight route?
Fly from Chicago O'Hare Intl to Montego Bay Sangster Intl for the best Chicago - Jamaica flight prices
How far in advance should I book a flight from Chicago to Jamaica?
You are more likely to see cheaper flights to Jamaica from Chicago 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 for as low as $493 on momondo.
What cabin class options are available on Chicago to Jamaica flights?
There are 3 cabin classes available to choose from on Chicago 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 to Jamaica flights?
No. A direct flight is the cheapest option for a flight between Chicago to Jamaica.
What is the cheapest airline that flies from Chicago to Jamaica?
JetBlue, Delta, and Southwest are the most popular carriers operating from Chicago to Jamaica
What airlines fly to Jamaica?
American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Jamaica from Chicago according to our data. American Airlines is the first choice among our users, with 63% of people opting to fly with this airline when traveling to Jamaica. Keep in mind that there are 6 different airlines that fly to Jamaica on a routine basis, so you have a few additional options to choose from.
Cheap Chicago to Jamaica flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Jamaica
Frequently asked questions about flying from Chicago to Jamaica
When did momondo last update prices for flights from Chicago to Jamaica?
Prices for flights from Chicago to Jamaica refresh daily.
How many operators does momondo search for flights from Chicago to Jamaica?
As of October 2026, there are 6 operators available to choose from for flights from Chicago to Jamaica.
How old do you have to be to fly from Chicago to Jamaica?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago 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 to Jamaica?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to Jamaica is Boeing 737-800 (85.47% of total bookings). The next most popular plane models are Boeing 737 MAX 9 (5.13%), Boeing 737 (4.10%), and Boeing 737 MAX 8 (2.74%).
Best airlines flying from Chicago to Jamaica
Compare and see reviews for airlines that fly from Chicago to Jamaica with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $158 | Free Cancellation | Rating 7.8 8,645 reviews | |||
| PriceFrom $172 | Free Cancellation | Rating 5.6 2,550 reviews | |||
| PriceFrom $301 | Free Cancellation | Rating 7.1 3,049 reviews | |||
| PriceFrom $302 | Free Cancellation | Rating 7.4 10,319 reviews | |||
| PriceFrom $314 | Free Cancellation | Rating 7.0 12,145 reviews | |||
| PriceFrom $467 | Free Cancellation | Rating 7.9 4,221 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Jamaica?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Jamaica. Millions of users trust and use momondo every year so you are in good hands.
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?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Jamaica.
I’m not ready to book a flight from Chicago to Jamaica right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Jamaica from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.