Cheap flights from Chicago (CHI) to Jamaica

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How to find the cheapest flight from
Chicago (CHI) to Jamaica

All the information you need to plan the best CHI to MBJ flight in 2022: compare Chicago to Jamaica flight prices with the expected peak season, weather and rainfall in Jamaica.
What is the cheapest month to fly from Chicago to Jamaica?

Our data shows that September tends to be the cheapest month to fly to Jamaica from Chicago. Users have commonly found prices around $534 for the month, but tickets can be as low as $353. Due to multiple factors, prepare for potentially higher prices in December.

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

Find a great deal and save up to 3% by booking at least 26 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago to Jamaica within the next two weeks, with the cheapest ticket starting at $499.

When is the cheapest time to fly from Chicago to Jamaica (CHI - JM)?

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

Cheap flights from Chicago to Jamaica in May, June 2022

The best prices found for CHI to Jamaica flights for May, June
29 May - 3 Jun
$387pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
MBJ
Montego Bay Sangster Intl
MBJ
Montego Bay Sangster Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
29 May - 3 Jun
$403pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
MBJ
Montego Bay Sangster Intl
MBJ
Montego Bay Sangster Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
21 Jun - 22 Jun
$404pp
MDW
Chicago Midway
Frontier
 
1 STOP
MBJ
Montego Bay Sangster Intl
MBJ
Montego Bay Sangster Intl
Frontier
   
2 STOPS
MDW
Chicago Midway

Chicago to Jamaica 2022 flight deals

Cheap flights to Jamaica from Chicago found for this year
9 Sep - 12 Sep
$325pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
KIN
Kingston Norman Manley
KIN
Kingston Norman Manley
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
9 Sep - 12 Sep
$340pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
KIN
Kingston Norman Manley
KIN
Kingston Norman Manley
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
11 Sep - 17 Sep
$366pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
KIN
Kingston Norman Manley
KIN
Kingston Norman Manley
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Non-stop flights to Jamaica from Chicago

Save time with Chicago to Jamaica direct flight deals
7 Aug - 11 Aug
$510pp
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
MBJ
Montego Bay Sangster Intl
MBJ
Montego Bay Sangster Intl
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
10 Aug - 11 Aug
$535pp
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
MBJ
Montego Bay Sangster Intl
MBJ
Montego Bay Sangster Intl
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
4 Jul - 9 Jul
$558pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
MBJ
Montego Bay Sangster Intl
MBJ
Montego Bay Sangster Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to Jamaica

Late deals on round-trip flights to Jamaica from Chicago, departing today and this week
29 May - 3 Jun
$387pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
MBJ
Montego Bay Sangster Intl
MBJ
Montego Bay Sangster Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
29 May - 3 Jun
$403pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
MBJ
Montego Bay Sangster Intl
MBJ
Montego Bay Sangster Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
28 May - 3 Jun
$417pp
ORD
Chicago O'Hare Intl
Spirit Airlines
   
2 STOPS
MBJ
Montego Bay Sangster Intl
MBJ
Montego Bay Sangster Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

One-way flights to Jamaica from Chicago

The cheapest one-way flights from Chicago to Jamaica
12:56 pm - 4:11 am
Frontier
2 Stops
15h 15m
ORD - MBJ
Frontier
$226
Kiwi.com
3:16 pm - 7:56 am
Spirit Airlines
2 Stops
16h 40m
ORD - MBJ
Spirit Airlines
$230
Kiwi.com
6:15 am - 1:15 pm
JetBlue
1 Stop
7h 00m
ORD - MBJ
JetBlue

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Chicago</span> to <span class="emphasized">Jamaica</span> flights.

Flight FAQs

From Chicago to Jamaica

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

Some of our airline partners flying from Chicago to Jamaica have new flexible policies in place due to COVID-19. American Airlines, United Airlines, and Spirit Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like American Airlines with this kind of flexibility.

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

Yes, there are multiple flights from Chicago to Jamaica for under $400. The cheapest flight booked recently is on Spirit Airlines for just $340, but on average you can expect to pay $388.

Are there nonstop flights from Chicago to Jamaica for under $600 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Jamaica under $600. A good price for a nonstop flight from Chicago to Jamaica is less than $619.

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

There are currently 20+ open flights from Chicago to Jamaica within the next 7 days for less than $400.

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

One-way options have recently been found by users for as low as $130 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $185 and JetBlue from $233 one-way.

What are the cheapest flights from Chicago to Jamaica?

On average you can expect to pay $1,047 for a flight from Chicago to Jamaica. The cheapest flight overall is $169 while the most popular route, (Chicago O'Hare Intl - Montego Bay Sangster Intl) is currently priced at $385.

What are the most popular routes from Chicago to Jamaica?

The most popular flight routes from Chicago to Jamaica are Chicago O'Hare Intl - Montego Bay Sangster Intl, Chicago Midway - Montego Bay Sangster Intl and Chicago O'Hare Intl - Kingston Norman Manley.

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

American Airlines, JetBlue and Copa Airlines are the most popular airlines when flying from Chicago to Jamaica.

COVID Restrictions

View COVID Travel Restrictions for Jamaica

Do I need a COVID test to fly to Jamaica from Chicago?

Information is based on travel restrictions from Chicago to Jamaica

Most visitors from Chicago can enter Jamaica without restrictions.

COVID-19 testing requirements
Visitors from Chicago are not required to present a negative COVID-19 PCR test or antigen result upon entering Jamaica.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Jamaica.

Documents
Immigration/Customs C5 card online - travelers are encouraged to submit their Immigration/Customs C5 card online


Do I need a test to fly back to Chicago from Jamaica?

Returning to Chicago from Jamaica

COVID-19 testing requirements
Visitors from Jamaica must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 1 day for RT-PCR (NAAT) and 1 day for Antigen (quick-test) before departing to Chicago.

Quarantine requirements
Visitors from Jamaica are not required to quarantine after entering Chicago.

Hide COVID Travel Restrictions for Jamaica

Destination points for flights from Chicago to Jamaica

Select to see more specific information for flights from Chicago to all places in Jamaica.

Destination information for Jamaica

Things to know before you go - useful duration and weather info for your trip from Chicago to Jamaica.
Today's exchange rate
$1 = $153.15

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Airports servicing

Montego Bay (MBJ)
Negril (NEG)
Ocho Rios (OCJ)

Top 7 airlines flying from Chicago to Jamaica

The chart below displays the airlines Cheapflights users traveling from Chicago to Jamaica choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Juneyao Airlines
$12 $19 No cancel fee 66%

We couldn't confirm the COVID-19 safety measures taken by Juneyao Airlines. Please check directly on their website for additional information.

Spirit Airlines
$111 $399 No cancel fee 65%
JetBlue
$134 $491 No cancel fee 62%
Frontier
$166 $390 No cancel fee 62%
American Airlines
$242 $611 No cancel fee 71%
United Airlines
$243 $533 No cancel fee 69%
Delta
$344 $670 No cancel fee N/A
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