HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$176+ Cheap flights from Jamaica to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — MDW
dic. 23 — dic. 301
lun. 12/23
lun. 12/30
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Jamaica to Midway with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Jamaica to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Jamaica (JM0) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated diciembre 18, 2024.

Round-trip from

$459
(Delta)

One-way from

$176
(Trip.com)
From Jamaica to Chicago Midway
Search Deals
One-way flight from Jamaica to Chicago Midway
Search Deals

Find flight deals from Jamaica to Midway

Best flights from Jamaica to Midway
Discover carefully curated flight deals from Jamaica to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated diciembre 18, 2024.

This Delta deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 1/164:49 pmMBJ - MDW
1 stop6h 31mDelta
dom. 1/196:00 amMDW - MBJ
1 stop8h 24mDelta
Deal found 12/17$459

Find flights from Jamaica to Midway within your budget

Customize your flight search to find flights from Jamaica to Midway 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, Cheapflights users made 2,558,603 searches. Data last updated diciembre 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

jue. 1/16

4:49 pm-10:20 pm

1 stop6h 31m

Chicago Midway

dom. 1/19

6:00 am-3:24 pm

1 stop8h 24m

$459

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

sáb. 1/18

2:20 pm-11:29 pm

1 stop10h 09m

$176

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

sáb. 2/8

2:49 pm-11:44 am

2 stops21h 55m

$208

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

mar. 1/14

8:00 am-4:21 pm

1 stop9h 21m

$258

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

sáb. 1/25

2:10 pm-5:25 pm

Nonstop4h 15m

$282

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

vie. 3/21

1:55 pm-5:18 pm

2 stops27h 23m

$436

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

Best time to book a flight from Jamaica to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Jamaica with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Jamaica to Midway

Get recent, data-driven insights about flights from Jamaica to Midway including ideal travel times, pricing trends, and more.

What is the cheapest time of day to fly from JM to MDW?

Find hourly flight availability from Jamaica to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated diciembre 18, 2024.

When flying from Jamaica to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated diciembre 18, 2024.
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

WestJet
7.3
Good
2,818 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,479 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

Find useful and relevant information for your journey from Jamaica to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Jamaica to Chicago Midway Airport one-way?

    $176 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Delta and Southwest, with prices starting from $258 and $282, respectively.

  • Can I find deals for flights from Jamaica to Midway that include hotel bookings?

    Yes. In addition to deals on Jamaica to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Jamaica to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Jamaica to Midway.

  • Can I find deals for business class flights from Jamaica to Midway?

    Yes. Cheapflights offers flight deals from Jamaica to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Jamaica to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Jamaica to Chicago Midway Airport (average of $160). Flying from Jamaica to Chicago Midway Airport in October is currently the most expensive (average of $232). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Jamaica to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Luis Munoz Marin Intl to O'Hare Intl flights
Luis Munoz Marin Intl to Midway flights
Punta Cana to O'Hare Intl flights
Santo Domingo to O'Hare Intl flights
Santo Domingo to Midway flights
Nassau to O'Hare Intl flights
Montego Bay to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
Punta Cana to Midway flights
Port of Spain to O'Hare Intl flights
Nassau to Midway flights
Kingston to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
George Town to O'Hare Intl flights
Montego Bay to Midway flights
Aguadilla to O'Hare Intl flights
St. John's to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Aguadilla to Midway flights
Road Town to O'Hare Intl flights
Roseau to O'Hare Intl flights
Vieques to O'Hare Intl flights
Simpson Bay to Midway flights
Christiansted to O'Hare Intl flights
Culebra to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Port Au Prince to O'Hare Intl flights
Port Au Prince to Midway flights

Top airline flying from Jamaica to Midway

Discover the top airline that operate flights from Jamaica to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated diciembre 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$332Average$588FlexibilityNo cancel feeOn-timeN/A
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.