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Cheap flights from Chicago Midway (MDW) to Jamaica

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How to find the cheapest flight from
Chicago Midway (MDW) to Jamaica

How far in advance should I book a flight from Chicago Midway to Jamaica?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 49 days in advance, which can save you up to 3% on flights from Chicago Midway to Jamaica compared to booking the week you need them. Waiting 49 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $441. For sooner than that we have options available in the next 3 days from $445.

What is the cheapest month to fly from Chicago Midway to Jamaica?

August is one of the best times of the year to fly to Jamaica from Chicago Midway. Prices for August average $452 per person but you can even find prices for as low as $210. The most expensive prices can be found in the month of December. Opting for a August flight can save you 29% on your journey compared to booking in August

Cheap flights from Chicago Midway to Jamaica in November, December 2020

The best prices found for MDW to Jamaica flights for November, December
3 Dec - 9 Dec
$359pp
MDW
Chicago Midway
Delta
 
1 STOP
MBJ
Montego Bay Sangster Intl
MBJ
Montego Bay Sangster Intl
Delta
 
1 STOP
MDW
Chicago Midway
14 Dec - 20 Dec
$447pp
MDW
Chicago Midway
Multiple Airlines
     
3 STOPS
MBJ
Montego Bay Sangster Intl
MBJ
Montego Bay Sangster Intl
Multiple Airlines
     
3 STOPS
MDW
Chicago Midway
19 Dec - 1 Jan
$453pp
MDW
Chicago Midway
Delta
 
1 STOP
MBJ
Montego Bay Sangster Intl
MBJ
Montego Bay Sangster Intl
Delta
 
1 STOP
MDW
Chicago Midway

Chicago Midway to Jamaica 2021 flight deals

Cheap flights to Jamaica from Chicago Midway found for next year
3 Dec - 12 Dec
$359pp
MDW
Chicago Midway
Delta
 
1 STOP
MBJ
Montego Bay Sangster Intl
MBJ
Montego Bay Sangster Intl
Delta
 
1 STOP
MDW
Chicago Midway
14 Dec - 20 Dec
$447pp
MDW
Chicago Midway
Multiple Airlines
     
3 STOPS
MBJ
Montego Bay Sangster Intl
MBJ
Montego Bay Sangster Intl
Multiple Airlines
     
3 STOPS
MDW
Chicago Midway
19 Dec - 1 Jan
$453pp
MDW
Chicago Midway
Delta
 
1 STOP
MBJ
Montego Bay Sangster Intl
MBJ
Montego Bay Sangster Intl
Delta
 
1 STOP
MDW
Chicago Midway

Last minute flights from Chicago Midway to Jamaica

Late deals on round-trip flights to Jamaica from Chicago Midway, departing today and this week
3 Dec - 9 Dec
$359pp
MDW
Chicago Midway
Delta
 
1 STOP
MBJ
Montego Bay Sangster Intl
MBJ
Montego Bay Sangster Intl
Delta
 
1 STOP
MDW
Chicago Midway
3 Dec - 10 Dec
$481pp
MDW
Chicago Midway
Delta
 
1 STOP
KIN
Kingston Norman Manley
KIN
Kingston Norman Manley
Delta
 
1 STOP
MDW
Chicago Midway
3 Dec - 10 Dec
$588pp
MDW
Chicago Midway
Delta
 
1 STOP
MBJ
Montego Bay Sangster Intl
MBJ
Montego Bay Sangster Intl
Delta
 
1 STOP
MDW
Chicago Midway

One-way flights to Jamaica from Chicago Midway

The cheapest one-way flights from Chicago Midway to Jamaica
1:08 am - 7:40 am
Delta
1 Stop
5h 32m
MDW - MBJ
Delta
$158
Delta
6:30 am - 2:44 pm
Delta
1 Stop
7h 14m
MDW - KIN
Delta
$209
Delta
1:08 am - 11:08 am
Delta
1 Stop
9h 00m
MDW - MBJ
Delta
$282
Delta

Related info for your journey

Useful info, stats and facts about Chicago Midway to Jamaica flights.

Flight FAQs

From Chicago Midway to Jamaica

Are flight prices decreasing from Chicago Midway to Jamaica due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Chicago Midway and Jamaica for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

What safety measures are being taken by airlines flying from Chicago Midway to Jamaica to control the spread of COVID-19?

New policies can now be found on Delta to help keep travelers safe while flying. New policies for travelers booking flights from Chicago Midway to Jamaica include masks being provided and required on board, daily cleaning and sanitization, use of HEPA filters, pre-flight testing for antibodies and symptoms, and socially distanced seating (for a limited time). Keep in mind that policies will vary by airline.

Which airlines flying from Chicago Midway to Jamaica have flexible cancellations due to COVID-19?

Due to the rapidly changing circumstances due to COVID-19, airlines like Delta, American Airlines, and United Airlines flying from Chicago Midway to Jamaica have implemented new flexible cancellation policies.

Can I find flights from Chicago Midway to Jamaica for under $400 on Cheapflights?

Yes, there are multiple flights from Chicago Midway to Jamaica for under $400. The cheapest flight booked recently is on Delta for just $359, but on average you can expect to pay $482.

Are there nonstop flights from Chicago Midway to Jamaica for under $400 on Cheapflights?

There are no nonstop flights from Chicago Midway to Jamaica, but Cheapflights can provide you with all the information you need to find the fastest route with the fewest stops.

Are there last-minute flights available from Chicago Midway to Jamaica for under $400?

There are currently 5+ open flights from Chicago Midway to Jamaica within the next 7 days for less than $400.

What days are nonstop flights available from Chicago Midway to Jamaica?

Nonstop flights are available for this route on the following days: Friday.

What are the most popular airlines that fly from Chicago Midway to Jamaica?

When booking a flight from Chicago Midway to Jamaica, you may want to consider flying on American Airlines, Delta or United Airlines as they are the most popular for this route.

What are the cheapest Flights from Chicago Midway to Jamaica?

Looking at all options, your cheapest flight can be booked for $459. While the most popular route (Chicago Midway - Montego Bay Sangster Intl) can be booked for $359 on average our data indicates $589 when flying from Chicago Midway to Jamaica

How long is the flight from Chicago Midway to Jamaica?

Delta can get you from Chicago Midway to Jamaica in just under 5h 32m. Your travel time can differ by up to .

What is the cheapest airline to fly from Chicago Midway to Jamaica round-trip?

According to our current data, Delta ($359), offers the cheapest pricing from Chicago Midway to Jamaica.

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

The cheapest airlines for a one-way flight from Chicago Midway to Jamaica are Delta ($158) and WestJet ($630).

Arrival points for flights from Chicago Midway to Jamaica

Destination information for Jamaica

Things to know before you go. Useful info for your trip from Chicago Midway to Jamaica
Today's exchange rate
$1 = $145.55

Airports servicing Chicago

Airports servicing

Montego Bay (MBJ)
Negril (NEG)
Ocho Rios (OCJ)
Home Caribbean Jamaica Cheap flights from Chicago Midway to Jamaica