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Cheap flights from Chicago to Montego Bay from $100

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 12/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
5:15 am - 12:02 pmORD-MBJ
5h 47m1 stop
Spirit Airlines Logo
12:57 pm - 12:18 amMBJ-ORD
12h 21m1 stop
$351Spirit Airlines
Find Deal
jue., ene. 8 - lun., ene. 12
Multiple Airlines Logo
4:11 pm - 9:35 amORD-MBJ
16h 24m1 stop
Multiple Airlines Logo
12:57 pm - 6:47 pmMBJ-ORD
6h 50m1 stop
$352Multiple Airlines
Find Deal
mié., ene. 14 - vie., ene. 23
American Airlines Logo
10:15 am - 3:28 pmORD-MBJ
4h 13mnonstop
American Airlines Logo
2:20 pm - 6:03 pmMBJ-ORD
4h 43mnonstop
$364American Airlines
Find Deal
vie., nov. 28 - lun., dic. 22
American Airlines Logo
8:05 am - 1:19 pmORD-MBJ
4h 14mnonstop
American Airlines Logo
1:58 pm - 5:37 pmMBJ-ORD
4h 39mnonstop
$365American Airlines
Find Deal
sáb., ene. 24 - jue., ene. 29
Frontier Logo
8:42 pm - 3:51 pmMDW-MBJ
18h 09m1 stop
Frontier Logo
3:31 pm - 8:46 amMBJ-MDW
18h 15m1 stop
$366Frontier
Find Deal
vie., dic. 5 - lun., dic. 8
Delta Logo
5:23 am - 12:52 pmORD-MBJ
6h 29m1 stop
Delta Logo
5:58 pm - 12:01 amMBJ-ORD
7h 03m1 stop
$372Delta
Find Deal
vie., nov. 28 - jue., dic. 4
Delta Logo
6:00 am - 12:52 pmMDW-MBJ
5h 52m1 stop
Delta Logo
3:38 pm - 8:54 amMBJ-MDW
18h 16m2 stops
$372Delta
Find Deal
vie., nov. 28 - jue., dic. 4
Frontier Logo
6:00 am - 3:47 pmMDW-MBJ
8h 47m1 stop
Frontier Logo
3:46 pm - 11:25 pmMBJ-MDW
8h 39m1 stop
$374Frontier
Find Deal
dom., ene. 18 - lun., ene. 26
Southwest Logo
5:05 am - 12:50 pmMDW-MBJ
6h 45m1 stop
Southwest Logo
1:50 pm - 10:25 pmMBJ-MDW
9h 35m1 stop
$473Southwest
Find Deal
mar., dic. 16 - mar., dic. 23
Southwest Logo
6:50 am - 2:10 pmMDW-MBJ
6h 20m1 stop
Southwest Logo
2:15 pm - 5:35 pmMBJ-MDW
4h 20mnonstop
$488Southwest
Find Deal
dom., ene. 18 - sáb., ene. 24

Spirit Airlines flights from Chicago to Montego Bay

Our best Spirit Airlines deals on Chicago to Montego Bay flight tickets
Spirit Airlines
Jan 8
ORD5:15 amChicago O'Hare Intl
5h 47m
1 stop
MBJ12:02 pmMontego Bay Sangster Intl
Jan 12
MBJ12:57 pmMontego Bay Sangster Intl
12h 21m
1 stop
ORD12:18 amChicago O'Hare Intl
$351
Find similar
Spirit Airlines
Feb 21
ORD5:15 amChicago O'Hare Intl
5h 47m
1 stop
MBJ12:02 pmMontego Bay Sangster Intl
Feb 28
MBJ1:00 pmMontego Bay Sangster Intl
6h 52m
1 stop
ORD6:52 pmChicago O'Hare Intl
$353
Find similar
Spirit Airlines
Jan 9
ORD5:15 amChicago O'Hare Intl
5h 47m
1 stop
MBJ12:02 pmMontego Bay Sangster Intl
Jan 23
MBJ12:57 pmMontego Bay Sangster Intl
6h 50m
1 stop
ORD6:47 pmChicago O'Hare Intl
$354
Find similar

American Airlines flights from Chicago to Montego Bay

Our best American Airlines deals on Chicago to Montego Bay flight tickets
American Airlines
Nov 28
ORD10:15 amChicago O'Hare Intl
4h 13m
MBJ3:28 pmMontego Bay Sangster Intl
Dec 22
MBJ2:20 pmMontego Bay Sangster Intl
4h 43m
ORD6:03 pmChicago O'Hare Intl
$364
Find similar
American Airlines
Jan 24
ORD8:05 amChicago O'Hare Intl
4h 14m
MBJ1:19 pmMontego Bay Sangster Intl
Jan 29
MBJ1:58 pmMontego Bay Sangster Intl
4h 39m
ORD5:37 pmChicago O'Hare Intl
$365
Find similar
American Airlines
Nov 28
ORD10:15 amChicago O'Hare Intl
4h 13m
MBJ3:28 pmMontego Bay Sangster Intl
Dec 4
MBJ3:12 pmMontego Bay Sangster Intl
4h 47m
ORD6:59 pmChicago O'Hare Intl
$366
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Montego Bay that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated noviembre 10, 2025.
Use the filters below to find and compare flights from Chicago to Montego Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

jue. 1/8

5:15 am-12:02 pm

1 stop5h 47m

Montego Bay Sangster Intl

lun. 1/12

12:57 pm-12:18 am

1 stop12h 21m

$351

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

mié. 1/14

4:11 pm-9:35 am

1 stop16h 24m

Montego Bay Sangster Intl

vie. 1/23

12:57 pm-6:47 pm

1 stop6h 50m

$352

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

vie. 11/28

10:15 am-3:28 pm

Nonstop4h 13m

Montego Bay Sangster Intl

lun. 12/22

2:20 pm-6:03 pm

Nonstop4h 43m

$364

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

sáb. 1/24

8:05 am-1:19 pm

Nonstop4h 14m

Montego Bay Sangster Intl

jue. 1/29

1:58 pm-5:37 pm

Nonstop4h 39m

$365

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

vie. 12/5

8:42 pm-3:51 pm

1 stop18h 09m

Montego Bay Sangster Intl

lun. 12/8

3:31 pm-8:46 am

1 stop18h 15m

$366

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

vie. 11/28

5:23 am-12:52 pm

1 stop6h 29m

Montego Bay Sangster Intl

jue. 12/4

5:58 pm-12:01 am

1 stop7h 03m

$372

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

vie. 11/28

6:00 am-12:52 pm

1 stop5h 52m

Montego Bay Sangster Intl

jue. 12/4

3:38 pm-8:54 am

2 stops18h 16m

$372

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

dom. 1/18

6:00 am-3:47 pm

1 stop8h 47m

Montego Bay Sangster Intl

lun. 1/26

3:46 pm-11:25 pm

1 stop8h 39m

$374

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mar. 12/16

5:05 am-12:50 pm

1 stop6h 45m

Montego Bay Sangster Intl

mar. 12/23

1:50 pm-10:25 pm

1 stop9h 35m

$473

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

dom. 1/18

6:50 am-2:10 pm

1 stop6h 20m

Montego Bay Sangster Intl

sáb. 1/24

2:15 pm-5:35 pm

Nonstop4h 20m

$488

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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?

What is the cheapest month to fly to Montego Bay?

If you aren’t able to travel to Montego Bay during the month of September, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $546.

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 Sunday. momondo users have found tickets for Sunday departures for as low as $557. 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 $690.

What is the cheapest time of day to depart on your flight to Montego Bay?

At noon is the cheapest time of day to fly from Chicago to Montego Bay when you can find flight prices for as low as $403. Flying to Montego Bay at noon is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $613.

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 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 $594 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 $530 on momondo.

What cabin class options are available on Chicago to Montego Bay Sangster Intl flights?

There are 3 cabin classes available to choose from on Chicago to Montego Bay Sangster Intl 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?

You could potentially save up to 5% on your flight if you consider stops on a Chicago to Montego Bay flight.

How have Chicago to Montego Bay flight prices changed over time?

As of November 2025, prices for Chicago to Montego Bay flights are approximately 9% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Montego Bay

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Montego Bay according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

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

Best Price Found

$195

Fastest flight time

3h 50m

Direct flights

Every day

Airports in Montego Bay

1 airport
The best one-way flight to Montego Bay from Chicago in the past 72 hours is $195. The best round-trip flight deal from Chicago to Montego Bay found on momondo in the last 72 hours is $421.
The fastest flight from Chicago to Montego Bay takes 3h 50m
Direct flights go from Chicago to Montego Bay every day.
There is 1 airport near Montego Bay: Montego Bay Sangster Intl (MBJ)
Search flight deals

  • 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 4h 13m.

  • 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?

  • 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?

  • What is the most popular airline from Chicago to Montego Bay?

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
DeltaPriceFrom $186Free CancellationRating
7.9
8,004 reviews
Search Delta flights
Spirit AirlinesPriceFrom $194Free CancellationRating
6.3
8,131 reviews
Search Spirit Airlines flights
FrontierPriceFrom $333Free CancellationRating
5.8
3,111 reviews
Search Frontier flights
United AirlinesPriceFrom $373Free CancellationRating
7.4
9,011 reviews
Search United Airlines flights
American AirlinesPriceFrom $441Free CancellationRating
7.2
11,047 reviews
Search American Airlines flights
SouthwestPriceFrom $549Free CancellationRating
8.0
4,238 reviews
Search Southwest flights

  • United Airlines Flights From Chicago to Montego Bay

    United Airlines flight deals from Chicago to Montego Bay start from $373 round-trip. Over the 7 United Airlines flights for this route in a normal week, average airfare is usually $626 round-trip - but some users have found much cheaper deals with momondo.

  • American Airlines Flights From Chicago to Montego Bay

    American Airlines is also a popular choice for this route. American Airlines flight deals for Chicago to Montego Bay start from as low as $441 round-trip, depending on your selected dates, with average American Airlines deals seen on momondo around $597. American Airlines operates 12 flights to Montego Bay from Chicago in an average week. Users have rated it 7.2/10 across 11,047 reviews.

Traveling to a place near Montego Bay?

Book flights to Montego Bay if you plan to visit one of these locations
Lucea
Falmouth
Treasure Beach
Whitehouse

Why 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.

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