Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Montego Bay from $159

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.
Frontier Logo
7:50 pm - 3:08 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
18h 18m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
4:23 pm - 6:16 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
26h 53m1 stop Atlanta Hartsfield-Jackson
$431Frontier
Thu, Nov 12 - Mon, Nov 16
Multiple Airlines Logo
7:15 am - 3:28 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
7h 13m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:20 pm - 1:13 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
19h 53m1 stop Toronto Pearson Intl
$431Multiple Airlines
Sat, Nov 14 - Mon, Nov 23
Multiple Airlines Logo
7:15 am - 2:28 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
7h 13m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
1:50 pm - 1:13 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
24h 23m1 stop Toronto Pearson Intl
$431Multiple Airlines
Sat, Oct 31 - Tue, Nov 3
American Airlines Logo
9:45 am - 2:59 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
4h 14mnonstop
American Airlines Logo
4:04 pm - 7:46 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 42mnonstop
$437American Airlines
Sun, Jan 24 - Fri, Jan 29
American Airlines Logo
9:45 am - 2:59 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
4h 14mnonstop
American Airlines Logo
4:04 pm - 7:46 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 42mnonstop
$437American Airlines
Tue, Feb 9 - Wed, Feb 10
JetBlue Logo
7:00 am - 2:57 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
6h 57m1 stop Fort Lauderdale
JetBlue Logo
3:00 pm - 11:38 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
9h 38m1 stop Fort Lauderdale
$439JetBlue
Sun, Nov 8 - Sat, Nov 21
Frontier Logo
2:04 pm - 1:08 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
22h 04m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
2:25 pm - 12:59 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
23h 34m1 stop Atlanta Hartsfield-Jackson
$441Frontier
Sun, Dec 6 - Mon, Dec 14
United Airlines Logo
5:00 am - 2:37 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
8h 37m1 stop Newark
United Airlines Logo
2:48 pm - 6:16 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 28mnonstop
$442United Airlines
Fri, Feb 26 - Sun, Mar 7
JetBlue Logo
6:00 am - 12:03 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
6h 03m1 stop Fort Lauderdale
JetBlue Logo
12:03 pm - 11:30 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
11h 27m1 stop Fort Lauderdale
$445JetBlue
Mon, Oct 5 - Sat, Oct 10
United Airlines Logo
8:40 am - 12:48 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
4h 08mnonstop
United Airlines Logo
2:01 pm - 6:27 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 26mnonstop
$468United Airlines
Mon, Oct 26 - Fri, Oct 30

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Southwest flights from Chicago to Montego Bay

Our best Southwest deals on Chicago to Montego Bay flight tickets
Southwest
Dec 7
MDW8:10 amChicago Midway
5h 35m
1 stop
MBJ2:45 pmMontego Bay Sangster Intl
Dec 12
MBJ2:15 pmMontego Bay Sangster Intl
9h 05m
1 stop
MDW10:20 pmChicago Midway
$463
Southwest
Dec 6
MDW5:05 amChicago Midway
8h 40m
2 stops
MBJ2:45 pmMontego Bay Sangster Intl
Dec 14
MBJ1:50 pmMontego Bay Sangster Intl
9h 45m
2 stops
MDW10:35 pmChicago Midway
$477
Southwest
Sep 26
MDW5:55 amChicago Midway
6h 30m
1 stop
MBJ12:25 pmMontego Bay Sangster Intl
Oct 3
MBJ12:55 pmMontego Bay Sangster Intl
9h 20m
1 stop
MDW10:15 pmChicago Midway
$482

Frontier flights from Chicago to Montego Bay

Our best Frontier deals on Chicago to Montego Bay flight tickets
Frontier
Sep 25
MDW6:46 pmChicago Midway
17h 16m
1 stop
MBJ12:02 pmMontego Bay Sangster Intl
Oct 30
MBJ3:23 pmMontego Bay Sangster Intl
8h 24m
1 stop
MDW11:47 pmChicago Midway
$441
Frontier
Nov 14
ORD7:15 amChicago O'Hare Intl
7h 13m
1 stop
MBJ3:28 pmMontego Bay Sangster Intl
Nov 22
MBJ2:01 pmMontego Bay Sangster Intl
10h 17m
1 stop
ORD11:18 pmChicago O'Hare Intl
$442
Frontier
Nov 7
ORD7:15 amChicago O'Hare Intl
7h 13m
1 stop
MBJ3:28 pmMontego Bay Sangster Intl
Nov 15
MBJ4:43 pmMontego Bay Sangster Intl
17h 34m
1 stop
ORD9:17 amChicago O'Hare Intl
$445

momondo Fare Finder

 
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

Cheapest round-trip

ChicagoMontego Bay

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

ORDMBJ

Chicago O'Hare Intl

Thu 11/12

7:50 pm-3:08 pm

1 stop18h 18m

Montego Bay Sangster Intl

Mon 11/16

4:23 pm-6:16 pm

1 stop26h 53m

$431

ChicagoMontego Bay

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

ORDMBJ

Chicago O'Hare Intl

Sat 11/14

7:15 am-3:28 pm

1 stop7h 13m

Montego Bay Sangster Intl

Mon 11/23

6:20 pm-1:13 pm

1 stop19h 53m

$431

ChicagoMontego Bay

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

ORDMBJ

Chicago O'Hare Intl

Sat 10/31

7:15 am-2:28 pm

1 stop7h 13m

Montego Bay Sangster Intl

Tue 11/3

1:50 pm-1:13 pm

1 stop24h 23m

$431

ChicagoMontego Bay

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

ORDMBJ

Chicago O'Hare Intl

Sun 1/24

9:45 am-2:59 pm

Nonstop4h 14m

Montego Bay Sangster Intl

Fri 1/29

4:04 pm-7:46 pm

Nonstop4h 42m

$437

ChicagoMontego Bay

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

ORDMBJ

Chicago O'Hare Intl

Tue 2/9

9:45 am-2:59 pm

Nonstop4h 14m

Montego Bay Sangster Intl

Wed 2/10

4:04 pm-7:46 pm

Nonstop4h 42m

$437

ChicagoMontego Bay

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

ORDMBJ

Chicago O'Hare Intl

Sun 11/8

7:00 am-2:57 pm

1 stop6h 57m

Montego Bay Sangster Intl

Sat 11/21

3:00 pm-11:38 pm

1 stop9h 38m

$439

ChicagoMontego Bay

MDW Chicago Midway - MBJ Montego Bay Sangster Intl

MDWMBJ

Chicago Midway

Sun 12/6

2:04 pm-1:08 pm

1 stop22h 04m

Montego Bay Sangster Intl

Mon 12/14

2:25 pm-12:59 pm

1 stop23h 34m

$441

ChicagoMontego Bay

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

ORDMBJ

Chicago O'Hare Intl

Fri 2/26

5:00 am-2:37 pm

1 stop8h 37m

Montego Bay Sangster Intl

Sun 3/7

2:48 pm-6:16 pm

Nonstop4h 28m

$442

ChicagoMontego Bay

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

ORDMBJ

Chicago O'Hare Intl

Mon 10/5

6:00 am-12:03 pm

1 stop6h 03m

Montego Bay Sangster Intl

Sat 10/10

12:03 pm-11:30 pm

1 stop11h 27m

$445
Quickest round-trip

ChicagoMontego Bay

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

ORDMBJ

Chicago O'Hare Intl

Mon 10/26

8:40 am-12:48 pm

Nonstop4h 08m

Montego Bay Sangster Intl

Fri 10/30

2:01 pm-6:27 pm

Nonstop4h 26m

$468

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $414 to $553.
The lowest price recently found on this route was $428.

What is the cheapest month to fly to Montego Bay?

If you aren’t able to travel to Montego Bay during the month of October, then flying in April is also cheap. Prices for this month can be found on momondo for an average of $472.

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 $596.

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 $529 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 $463 on momondo.

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

There are 4 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 September 2026, prices for Chicago to Montego Bay flights are approximately 30% 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

$159

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 $159. The best round-trip flight deal from Chicago to Montego Bay found on momondo in the last 72 hours is $431.
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
FrontierPriceFrom $144Free CancellationRating
5.6
2,601 reviews
Search Frontier flights
DeltaPriceFrom $162Free CancellationRating
7.8
8,568 reviews
Search Delta flights
JetBluePriceFrom $297Free CancellationRating
7.1
3,038 reviews
Search JetBlue flights
United AirlinesPriceFrom $302Free CancellationRating
7.4
10,215 reviews
Search United Airlines flights
American AirlinesPriceFrom $317Free CancellationRating
7.1
12,062 reviews
Search American Airlines flights
SouthwestPriceFrom $467Free CancellationRating
8.0
4,189 reviews
Search Southwest flights

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.

An easier way to manage your Montego Bay trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 10/16
Fri 10/23
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Jamaica