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Cheap flights from Chicago to Montego Bay from $182

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Montego Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
6:05 am - 2:35 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
7h 30m1 stop Miami
American Airlines Logo
4:18 pm - 7:58 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 40mnonstop
$465American Airlines
Wed, Jan 20 - Wed, Jan 27
Air Canada Logo
10:15 am - 12:50 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
25h 35m1 stop Toronto Pearson Intl
Air Canada Logo
1:50 pm - 9:23 amMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
20h 33m1 stop Toronto Pearson Intl
$465Air Canada
Sun, Nov 15 - Sun, Nov 22
Air Canada Logo
5:58 pm - 1:25 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
18h 27m2 stops Ottawa Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
1:50 pm - 9:23 amMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
20h 33m1 stop Toronto Pearson Intl
$465Air Canada
Sat, Nov 14 - Tue, Nov 24
JetBlue Logo
7:00 am - 2:06 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
6h 06m1 stop Fort Lauderdale
JetBlue Logo
2:30 pm - 11:47 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
10h 17m1 stop Fort Lauderdale
$466JetBlue
Tue, Feb 2 - Tue, Feb 16
American Airlines Logo
10:05 am - 3:18 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
4h 13mnonstop
American Airlines Logo
1:25 pm - 11:30 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
11h 05m1 stop Philadelphia
$467American Airlines
Sun, Jan 24 - Fri, Jan 29
JetBlue Logo
7:45 pm - 9:38 amORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
12h 53m1 stop Fort Lauderdale
JetBlue Logo
2:40 pm - 11:42 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
10h 02m1 stop Fort Lauderdale
$469JetBlue
Sat, Jan 23 - Wed, Jan 27
Frontier Logo
12:28 pm - 1:17 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
23h 49m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
2:22 pm - 4:06 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
26h 44m1 stop Atlanta Hartsfield-Jackson
$472Frontier
Sat, Dec 5 - Thu, Dec 10
Southwest Logo
8:10 am - 2:45 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
5h 35m1 stop Orlando
Southwest Logo
1:50 pm - 10:45 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
9h 55m2 stops Orlando Nashville Intl
$476Southwest
Tue, Dec 1 - Tue, Dec 8
Frontier Logo
6:42 pm - 12:56 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
17h 14m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
2:01 pm - 8:14 amMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
19h 13m1 stop Atlanta Hartsfield-Jackson
$477Frontier
Thu, Nov 19 - Mon, Nov 23
Southwest Logo
8:10 am - 2:45 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
5h 35m1 stop Orlando
Southwest Logo
1:50 pm - 9:20 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 30m1 stop Orlando
$479Southwest
Tue, Dec 1 - Tue, Dec 8

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Air Canada flights from Chicago to Montego Bay

Our best Air Canada deals on Chicago to Montego Bay flight tickets
Air Canada
Nov 14
ORD5:58 pmChicago O'Hare Intl
18h 27m
2 stops
MBJ1:25 pmMontego Bay Sangster Intl
Nov 24
MBJ1:50 pmMontego Bay Sangster Intl
20h 33m
1 stop
ORD9:23 amChicago O'Hare Intl
$465
Air Canada
Oct 31
ORD3:45 pmChicago O'Hare Intl
21h 05m
2 stops
MBJ12:50 pmMontego Bay Sangster Intl
Nov 3
MBJ1:50 pmMontego Bay Sangster Intl
20h 33m
1 stop
ORD9:23 amChicago O'Hare Intl
$468
Air Canada
Nov 14
ORD5:58 pmChicago O'Hare Intl
18h 27m
2 stops
MBJ1:25 pmMontego Bay Sangster Intl
Nov 21
MBJ6:20 pmMontego Bay Sangster Intl
17h 47m
2 stops
ORD11:07 amChicago O'Hare Intl
$469

Delta flights from Chicago to Montego Bay

Our best Delta deals on Chicago to Montego Bay flight tickets
Delta
Jan 24
MDW6:00 amChicago Midway
8h 25m
1 stop
MBJ3:25 pmMontego Bay Sangster Intl
Jan 29
MBJ2:20 pmMontego Bay Sangster Intl
8h 50m
1 stop
MDW10:10 pmChicago Midway
$490
Delta
Nov 9
ORD5:30 amChicago O'Hare Intl
10h 27m
1 stop
MBJ4:57 pmMontego Bay Sangster Intl
Nov 12
MBJ6:12 pmMontego Bay Sangster Intl
14h 37m
2 stops
ORD7:49 amChicago O'Hare Intl
$500
Delta
Jan 24
MDW6:00 amChicago Midway
9h 44m
1 stop
MBJ4:44 pmMontego Bay Sangster Intl
Jan 29
MBJ6:09 pmMontego Bay Sangster Intl
6h 46m
1 stop
MDW11:55 pmChicago Midway
$512

momondo Fare Finder

 
Use the filters below to find and compare flights from Chicago to Montego Bay that are best for you.

Fly from

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Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Wed 1/20

6:05 am-2:35 pm

1 stop7h 30m

Montego Bay Sangster Intl

Wed 1/27

4:18 pm-7:58 pm

Nonstop4h 40m

$465

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Sun 11/15

10:15 am-12:50 pm

1 stop25h 35m

Montego Bay Sangster Intl

Sun 11/22

1:50 pm-9:23 am

1 stop20h 33m

$465

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Sat 11/14

5:58 pm-1:25 pm

2 stops18h 27m

Montego Bay Sangster Intl

Tue 11/24

1:50 pm-9:23 am

1 stop20h 33m

$465

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Tue 2/2

7:00 am-2:06 pm

1 stop6h 06m

Montego Bay Sangster Intl

Tue 2/16

2:30 pm-11:47 pm

1 stop10h 17m

$466

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

1:25 pm-11:30 pm

1 stop11h 05m

$467

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Sat 1/23

7:45 pm-9:38 am

1 stop12h 53m

Montego Bay Sangster Intl

Wed 1/27

2:40 pm-11:42 pm

1 stop10h 02m

$469

ChicagoMontego Bay

MDW Chicago Midway - MBJ Montego Bay Sangster Intl

MDWMBJ

Chicago Midway

Sat 12/5

12:28 pm-1:17 pm

1 stop23h 49m

Montego Bay Sangster Intl

Thu 12/10

2:22 pm-4:06 pm

1 stop26h 44m

$472

ChicagoMontego Bay

MDW Chicago Midway - MBJ Montego Bay Sangster Intl

MDWMBJ

Chicago Midway

Tue 12/1

8:10 am-2:45 pm

1 stop5h 35m

Montego Bay Sangster Intl

Tue 12/8

1:50 pm-10:45 pm

2 stops9h 55m

$476

ChicagoMontego Bay

MDW Chicago Midway - MBJ Montego Bay Sangster Intl

MDWMBJ

Chicago Midway

Thu 11/19

6:42 pm-12:56 pm

1 stop17h 14m

Montego Bay Sangster Intl

Mon 11/23

2:01 pm-8:14 am

1 stop19h 13m

$477

ChicagoMontego Bay

MDW Chicago Midway - MBJ Montego Bay Sangster Intl

MDWMBJ

Chicago Midway

Tue 12/1

8:10 am-2:45 pm

1 stop5h 35m

Montego Bay Sangster Intl

Tue 12/8

1:50 pm-9:20 pm

1 stop8h 30m

$479

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?

Prices are currently typical for flights on this route.

Typical prices usually range from $449 to $697.
The lowest price recently found on this route was $465.

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 September is also cheap. Prices for this month can be found on momondo for an average of $504.

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 $485. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Montego Bay on Saturday is $632.

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 $567 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 $479 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.

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

As of October 2026, prices for Chicago to Montego Bay flights are approximately 67% more expensive 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

$182

Fastest flight time

3h 55m

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 $182. The best round-trip flight deal from Chicago to Montego Bay found on momondo in the last 72 hours is $465.
The fastest flight from Chicago to Montego Bay takes 3h 55m
Direct flights go from Chicago to Montego Bay every day.
There is 1 airport in Montego Bay. From Chicago there are direct flights to Montego Bay Sangster Intl (MBJ).
Search flight deals

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?

  • 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 $158Free CancellationRating
7.8
8,681 reviews
Search Delta flights
FrontierPriceFrom $172Free CancellationRating
5.5
2,516 reviews
Search Frontier flights
JetBluePriceFrom $301Free CancellationRating
7.1
3,066 reviews
Search JetBlue flights
American AirlinesPriceFrom $312Free CancellationRating
7.0
12,189 reviews
Search American Airlines flights
United AirlinesPriceFrom $322Free CancellationRating
7.3
10,441 reviews
Search United Airlines flights
SouthwestPriceFrom $467Free CancellationRating
7.9
4,218 reviews
Search Southwest flights

  • United Airlines Flights From Chicago to Montego Bay

    United Airlines flight deals from Chicago to Montego Bay start from $322 round-trip. Over the 6 United Airlines flights for this route in a normal week, average airfare is usually $625 round-trip - but some users have found much cheaper deals with momondo.

Traveling to a place near Montego Bay?

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