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Cheap flights from Montego Bay to Chicago from $153

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Montego Bay to Chicago departing on 2/7. 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

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Frontier Logo
2:35 pm - 10:44 pm
MBJ
-
ORD
9h 09m1 stop
Frontier Logo
6:03 am - 1:30 pm
ORD
-
MBJ
6h 27m1 stop
$304Frontier
Sat, Jan 24 - Sat, Jan 31
Multiple Airlines Logo
2:35 pm - 1:37 pm
MBJ
-
ORD
24h 02m1 stop
Multiple Airlines Logo
5:15 am - 12:02 pm
ORD
-
MBJ
5h 47m1 stop
$311Multiple Airlines
Sat, Jan 24 - Mon, Jan 26
Frontier Logo
3:47 pm - 10:24 pm
MBJ
-
ORD
7h 37m1 stop
Frontier Logo
6:05 am - 2:29 pm
ORD
-
MBJ
7h 24m1 stop
$322Frontier
Thu, Dec 25 - Wed, Dec 31
Spirit Airlines Logo
1:05 pm - 12:30 am
MBJ
-
ORD
12h 25m1 stop
Spirit Airlines Logo
5:32 pm - 12:02 pm
ORD
-
MBJ
17h 30m1 stop
$330Spirit Airlines
Sat, Dec 27 - Sat, Jan 31
American Airlines Logo
3:51 pm - 7:29 pm
MBJ
-
ORD
4h 38mnonstop
American Airlines Logo
10:11 am - 3:24 pm
ORD
-
MBJ
4h 13mnonstop
$341American Airlines
Thu, Dec 25 - Wed, Dec 31
Multiple Airlines Logo
2:35 pm - 8:18 am
MBJ
-
ORD
18h 43m2 stops
Multiple Airlines Logo
5:15 am - 12:02 pm
ORD
-
MBJ
5h 47m1 stop
$342Multiple Airlines
Sat, Jan 24 - Mon, Jan 26
Delta Logo
8:00 am - 5:22 pm
MBJ
-
ORD
10h 22m2 stops
Delta Logo
5:30 am - 12:58 pm
ORD
-
MBJ
6h 28m1 stop
$346Delta
Thu, Dec 25 - Wed, Dec 31
American Airlines Logo
5:28 pm - 11:27 pm
MBJ
-
ORD
6h 59m1 stop
American Airlines Logo
10:09 am - 3:22 pm
ORD
-
MBJ
4h 13mnonstop
$372American Airlines
Sat, Jan 24 - Mon, Jan 26
Spirit Airlines Logo
1:05 pm - 12:30 am
MBJ
-
ORD
12h 25m1 stop
Spirit Airlines Logo
12:44 pm - 12:02 pm
ORD
-
MBJ
22h 18m2 stops
$389Spirit Airlines
Sat, Dec 27 - Sat, Jan 31
American Airlines Logo
10:45 am - 11:50 pm
MBJ
-
ORD
13h 05m1 stop
American Airlines Logo
6:45 am - 1:15 pm
ORD
-
MBJ
6h 30m1 stop
$399American Airlines
Tue, Apr 7 - Tue, Apr 14

Frontier flights from Montego Bay to Chicago O'Hare Intl Airport

Our best Frontier deals on Montego Bay to Chicago O'Hare Intl Airport flight tickets
Frontier
Jan 24
MBJ2:35 pmMontego Bay Sangster Intl
9h 09m
1 stop
ORD10:44 pmChicago O'Hare Intl
Jan 31
ORD6:03 amChicago O'Hare Intl
6h 27m
1 stop
MBJ1:30 pmMontego Bay Sangster Intl
$304
Find similar
Frontier
Dec 25
MBJ3:47 pmMontego Bay Sangster Intl
7h 37m
1 stop
ORD10:24 pmChicago O'Hare Intl
Dec 31
ORD6:05 amChicago O'Hare Intl
7h 24m
1 stop
MBJ2:29 pmMontego Bay Sangster Intl
$322
Find similar
Frontier
Dec 23
MBJ3:47 pmMontego Bay Sangster Intl
7h 37m
1 stop
ORD10:24 pmChicago O'Hare Intl
Dec 28
ORD8:09 pmChicago O'Hare Intl
17h 20m
2 stops
MBJ2:29 pmMontego Bay Sangster Intl
$462
Find similar

Spirit Airlines flights from Montego Bay to Chicago O'Hare Intl Airport

Our best Spirit Airlines deals on Montego Bay to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines
Dec 27
MBJ1:05 pmMontego Bay Sangster Intl
12h 25m
1 stop
ORD12:30 amChicago O'Hare Intl
Jan 31
ORD5:32 pmChicago O'Hare Intl
17h 30m
1 stop
MBJ12:02 pmMontego Bay Sangster Intl
$330
Find similar
Spirit Airlines
Dec 27
MBJ1:05 pmMontego Bay Sangster Intl
12h 25m
1 stop
ORD12:30 amChicago O'Hare Intl
Jan 31
ORD12:44 pmChicago O'Hare Intl
22h 18m
2 stops
MBJ12:02 pmMontego Bay Sangster Intl
$389
Find similar
Spirit Airlines
Dec 27
MBJ1:05 pmMontego Bay Sangster Intl
12h 25m
1 stop
ORD12:30 amChicago O'Hare Intl
Jan 31
ORD3:22 pmChicago O'Hare Intl
19h 40m
3 stops
MBJ12:02 pmMontego Bay Sangster Intl
$416
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Montego Bay to Chicago O'Hare Intl Airport 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 December 10, 2025.
Use the filters below to find and compare flights from Montego Bay to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 1/24

2:35 pm-10:44 pm

1 stop9h 09m

Chicago O'Hare Intl

Sat 1/31

6:03 am-1:30 pm

1 stop6h 27m

$304

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 1/24

2:35 pm-1:37 pm

1 stop24h 02m

Chicago O'Hare Intl

Mon 1/26

5:15 am-12:02 pm

1 stop5h 47m

$311

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 12/25

3:47 pm-10:24 pm

1 stop7h 37m

Chicago O'Hare Intl

Wed 12/31

6:05 am-2:29 pm

1 stop7h 24m

$322

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 12/27

1:05 pm-12:30 am

1 stop12h 25m

Chicago O'Hare Intl

Sat 1/31

5:32 pm-12:02 pm

1 stop17h 30m

$330

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 12/25

3:51 pm-7:29 pm

Nonstop4h 38m

Chicago O'Hare Intl

Wed 12/31

10:11 am-3:24 pm

Nonstop4h 13m

$341

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 1/24

2:35 pm-8:18 am

2 stops18h 43m

Chicago O'Hare Intl

Mon 1/26

5:15 am-12:02 pm

1 stop5h 47m

$342

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 12/25

8:00 am-5:22 pm

2 stops10h 22m

Chicago O'Hare Intl

Wed 12/31

5:30 am-12:58 pm

1 stop6h 28m

$346

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 1/24

5:28 pm-11:27 pm

1 stop6h 59m

Chicago O'Hare Intl

Mon 1/26

10:09 am-3:22 pm

Nonstop4h 13m

$372

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 12/27

1:05 pm-12:30 am

1 stop12h 25m

Chicago O'Hare Intl

Sat 1/31

12:44 pm-12:02 pm

2 stops22h 18m

$389

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 4/7

10:45 am-11:50 pm

1 stop13h 05m

Chicago O'Hare Intl

Tue 4/14

6:45 am-1:15 pm

1 stop6h 30m

$399

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 Chicago from

How to get the cheapest flight ticket from Montego Bay to Chicago O'Hare Intl Airport

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 Chicago O'Hare Intl Airport?

The month of February is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Montego Bay averaging around $388.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $428. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Montego Bay because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $542.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Montego Bay in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $454 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $492. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Montego Bay Sangster Intl to Chicago O'Hare Intl flight route?

Fly from Montego Bay Sangster Intl to Chicago O'Hare Intl for the best Montego Bay Sangster Intl - Chicago O'Hare Intl flight prices

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

There are 3 cabin classes available to choose from on Montego Bay Sangster Intl to Chicago O'Hare 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 Montego Bay to Chicago O'Hare Intl Airport flights?

You could potentially save up to 10% on your flight if you consider stops on a Montego Bay to Chicago O'Hare Intl Airport flight.

How have Montego Bay to Chicago O'Hare Intl Airport flight prices changed over time?

As of December 2025, prices for Montego Bay to Chicago O'Hare Intl Airport flights are approximately 6% cheaper when compared to flights at the same time last year.

When to book flights from Montego Bay to Chicago O'Hare Intl Airport

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

Cheap Montego Bay to Chicago O'Hare Intl Airport (MBJ to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Montego Bay to Chicago O'Hare Intl Airport

Best Price Found

$251

Fastest flight time

4h 29m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Montego Bay in the past 72 hours is $251. The best round-trip flight deal from Montego Bay to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $387.
The fastest flight from Montego Bay to Chicago O'Hare Intl Airport takes 4h 29m
Direct flights go from Montego Bay to Chicago O'Hare Intl Airport every day.
Search flight deals

  • How far is Montego Bay Sangster Intl to Chicago O'Hare Intl by plane?

    The distance between Montego Bay Sangster Intl and Chicago O'Hare Intl is about 1726.0 mi. A reasonable flight in good conditions will take 4h 29m.

  • When did momondo last update prices for flights from Montego Bay Sangster Intl Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Montego Bay Sangster Intl Airport to Chicago O'Hare Intl Airport refresh daily.

  • How many operators does momondo search for flights from Montego Bay Sangster Intl Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Montego Bay Sangster Intl Airport to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Montego Bay Sangster Intl Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The required travel and health documents for your Chicago O'Hare 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 Chicago O'Hare 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 Montego Bay to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Montego Bay to Chicago O'Hare Intl Airport?

Best airlines flying from Montego Bay to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Montego Bay to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $256Free CancellationRating
6.3
8,173 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $348Free CancellationRating
7.2
11,047 reviews
Search American Airlines flights
United AirlinesPriceFrom $349Free CancellationRating
7.4
9,092 reviews
Search United Airlines flights

  • American Airlines Flights From Montego Bay to Chicago O'Hare Intl Airport

    American Airlines flight deals from Montego Bay to Chicago O'Hare Intl Airport start from $348 round-trip. Over the 7 American Airlines flights for this route in a normal week, average airfare is usually $476 round-trip - but some users have found much cheaper deals with momondo.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
South Haven
Schaumburg
Rockford
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Tinley Park
Janesville
Aurora
Elgin
Benton Harbor

Why use momondo?

Why should I use momondo to find a flight deal from Montego Bay to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Montego Bay.

Can I find flights from Montego Bay to Chicago with flexible booking policies on momondo?

Flights from Montego Bay to Chicago 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 Montego Bay to Chicago?

Once all potential Montego Bay to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Montego Bay to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Montego Bay and alert you when they change.

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