Cheap flights from Chicago to Montego Bay 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 Montego Bay 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 Montego Bay from
How to get the cheapest flight ticket from Chicago to Montego Bay
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 typical price of a round-trip flight between Chicago and Montego Bay?
Prices are currently typical for flights on this route.
Typical prices usually range from $435 to $766.The lowest price recently found on this route was $442.
What is the cheapest month to fly to Montego Bay?
If you aren’t able to travel to Montego Bay 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 $502.
What is the cheapest day to depart on your flight to Montego Bay?
On average, the least expensive day to fly to Montego Bay from Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $479. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Thursday as prices are generally higher than usual. According to our data, the average ticket price to Montego Bay on Thursday is $603.
What is the cheapest Chicago to Montego Bay Sangster Intl flight route?
Fly from Chicago O'Hare Intl to Montego Bay Sangster Intl for the best Chicago - Montego Bay Sangster Intl flight prices
How far in advance should I book a flight from Chicago to Montego Bay?
You are more likely to see cheaper flights to Montego Bay from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Montego Bay for around $550 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Montego Bay from Chicago for as low as $493 on momondo.
What cabin class options are available on Chicago to Montego Bay flights?
There are 3 cabin classes available to choose from on Chicago to Montego Bay 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 Montego Bay flights?
No. A direct flight is the cheapest option for a flight between Chicago to Montego Bay.
What is the cheapest airline that flies from Chicago to Montego Bay Sangster Intl?
JetBlue, Delta, and Southwest are the most popular carriers operating from Chicago to Montego Bay Sangster Intl
What airlines fly to Montego Bay?
American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Montego Bay 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 Montego Bay. Keep in mind that there are 6 different airlines that fly to Montego Bay on a routine basis, so you have a few additional options to choose from.
Which airport is the most popular layover for flights between Chicago and Montego Bay?
Orlando (MCO) was the most common stop: 33% of momondo users choosing 1-stop flights on this route connected there.
Which layover airport offers the lowest fares from Chicago to Montego Bay?
Flights via Toronto (YYZ) offer the lowest average round-trip price of $453.
Which layover airport has the shortest travel time from Chicago to Montego Bay?
Flights connecting via Orlando (MCO) have the shortest average one-way travel time: 5h 45m.
Which layover airport has the shortest connection time from Chicago to Montego Bay?
Orlando (MCO) has the shortest average layover time for this route: 2h 23m.
When to book flights from Chicago to Montego Bay
Cheap Chicago to Montego Bay (CHI to MBJ) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Montego Bay
Frequently asked questions about flying from Chicago to Montego Bay
How far is Chicago to Montego Bay Sangster Intl by plane?
The distance between Chicago and Montego Bay Sangster Intl is about 1713.9 mi. A reasonable flight in good conditions will take 3h 55m.
When did momondo last update prices for flights from Chicago to Montego Bay Sangster Intl Airport?
Prices for flights from Chicago to Montego Bay Sangster Intl Airport refresh daily.
How many operators does momondo search for flights from Chicago to Montego Bay Sangster Intl Airport?
The number of operators available for flights from Chicago to Montego Bay Sangster Intl Airport is 6 as of October 2026.
How old do you have to be to fly from Chicago to Montego Bay Sangster Intl Airport?
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 to Montego Bay Sangster Intl Airport.
What documentation or ID do you need to fly to Montego Bay Sangster Intl Airport?
The required travel and health documents for your Montego Bay Sangster Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Montego Bay Sangster Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Chicago to Montego Bay?
momondo data reveals that the most frequently booked plane model on the route from Chicago to Montego Bay is Boeing 737-800, representing 85.47% of all bookings. The subsequent popular models are Boeing 737 MAX 9 at 5.13%, Boeing 737 at 4.10%, and Boeing 737 MAX 8 at 2.74%.
What is the most popular airline from Chicago to Montego Bay?
Based on momondo bookings for flights between Chicago and Montego Bay, the leading airline is American Airlines, making up 55% of the total bookings. Other popular airlines include United Airlines with 28%, Southwest with 8%, and Frontier with 4%.
Best airlines flying from Chicago to Montego Bay
Compare and see reviews for airlines that fly from Chicago to Montego Bay with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $158 | Free Cancellation | Rating 7.8 8,646 reviews | |||
| PriceFrom $172 | Free Cancellation | Rating 5.6 2,551 reviews | |||
| PriceFrom $301 | Free Cancellation | Rating 7.1 3,048 reviews | |||
| PriceFrom $302 | Free Cancellation | Rating 7.4 10,319 reviews | |||
| PriceFrom $314 | Free Cancellation | Rating 7.0 12,146 reviews | |||
| PriceFrom $467 | Free Cancellation | Rating 7.9 4,224 reviews |
Traveling to a place near Montego Bay?
Book flights to Montego Bay if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Chicago to Montego Bay?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Montego Bay. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from Chicago to Montego Bay with flexible booking policies on momondo?
Flights from Chicago to Montego Bay 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 Montego Bay?
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 Montego Bay from Chicago.
I’m not ready to book a flight from Chicago to Montego Bay right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Montego Bay 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.