Cheap flights from Chicago (CHI) to Jamaica from $99
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 5/14. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
CHI — MBJ
Apr 30 — May 71
From?
To?
1 adult, Economy
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How far in advance should I book a flight from Chicago to Jamaica?
Find a great deal and save up to 35% by booking at least 47 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 $440.
What is the cheapest month to fly from Chicago to Jamaica?
Our data shows that August tends to be the cheapest month to fly to Jamaica from Chicago. Users have commonly found prices around $559 for the month, but tickets can be as low as $227. Due to multiple factors, prepare for potentially higher prices in December.
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 American Airlines flights from Chicago to Jamaica
Explore cheap flight options specifically provided by American Airlines for the route between Chicago and Jamaica. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 3,068,701 searches. Data last updated April 25, 2024.
Take a look at some of the lowest-priced American Airlines flights heading from Chicago to Jamaica. Make sure to check back often as deals are often changing.
Sun 7/78:45 amORD - MBJ
Nonstop3h 55mAmerican Airlines
Thu 7/112:05 pmMBJ - ORD
Nonstop4h 30mAmerican Airlines
Deal found 4/24$393
Sun 7/75:28 amORD - MBJ
1 stop10h 21mAmerican Airlines
Thu 7/112:05 pmMBJ - ORD
Nonstop4h 30mAmerican Airlines
Deal found 4/24$396
Tue 5/79:10 amORD - MBJ
Nonstop4h 00mAmerican Airlines
Fri 5/1010:35 amMBJ - ORD
1 stop13h 22mAmerican Airlines
Deal found 4/24$403
Tue 4/308:55 amORD - MBJ
Nonstop4h 05mAmerican Airlines
Tue 5/710:35 amMBJ - ORD
1 stop22h 32mAmerican Airlines
Deal found 4/25$414
Sat 6/297:05 amORD - MBJ
1 stop8h 35mAmerican Airlines
Thu 7/42:05 pmMBJ - ORD
Nonstop4h 30mAmerican Airlines
Deal found 4/25$446
Tue 6/188:50 amORD - MBJ
Nonstop4h 05mAmerican Airlines
Fri 6/282:05 pmMBJ - ORD
Nonstop4h 30mAmerican Airlines
Deal found 4/24$456
Tue 4/308:55 amORD - MBJ
Nonstop4h 05mAmerican Airlines
Tue 5/72:05 pmMBJ - ORD
Nonstop4h 30mAmerican Airlines
Deal found 4/25$458
Wed 5/16:35 amORD - MBJ
1 stop7h 37mAmerican Airlines
Sun 5/52:00 pmMBJ - ORD
Nonstop4h 35mAmerican Airlines
Deal found 4/24$461
Thu 5/25:12 pmORD - MBJ
1 stop17h 08mAmerican Airlines
Thu 5/92:05 pmMBJ - ORD
Nonstop4h 30mAmerican Airlines
Deal found 4/25$463
Cheap Frontier flights from Chicago to Jamaica
Explore cheap flight options specifically provided by Frontier for the route between Chicago and Jamaica. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 3,068,701 searches. Data last updated April 25, 2024.
Take a gander at the lowest prices we've found on Frontier flights from Chicago to Jamaica. If these deals don't fit your criteria, make sure to check back soon as new deals are always added.
Thu 5/210:17 pmMDW - MBJ
1 stop9h 03mFrontier
Mon 5/63:34 pmMBJ - MDW
1 stop27h 41mFrontier
Deal found 4/24$258
Wed 5/87:00 amMDW - MBJ
1 stop24h 20mFrontier
Sat 5/1111:51 amMBJ - MDW
1 stop10h 50mFrontier
Deal found 4/24$282
Thu 5/910:17 pmMDW - MBJ
1 stop9h 03mFrontier
Sun 5/123:09 pmMBJ - MDW
1 stop23h 30mFrontier
Deal found 4/24$284
Thu 5/210:17 pmMDW - MBJ
1 stop9h 03mFrontier
Mon 5/63:34 pmMBJ - MDW
2 stops32h 42mFrontier
Deal found 4/24$287
Thu 5/210:17 pmMDW - MBJ
1 stop9h 03mFrontier
Thu 5/98:32 amMBJ - MDW
1 stop12h 55mFrontier
Deal found 4/25$317
Mon 4/296:55 amMDW - MBJ
1 stop24h 25mFrontier
Wed 5/13:34 pmMBJ - MDW
1 stop22h 19mFrontier
Deal found 4/25$334
Thu 5/212:42 pmMDW - MBJ
2 stops18h 38mFrontier
Mon 5/63:34 pmMBJ - MDW
2 stops49h 39mFrontier
Deal found 4/24$336
Tue 4/307:00 amMDW - MBJ
1 stop7h 53mFrontier
Tue 5/78:32 amMBJ - MDW
1 stop10h 43mFrontier
Deal found 4/25$340
Tue 5/214:32 pmMDW - MBJ
1 stop22h 17mFrontier
Tue 5/288:07 amMBJ - MDW
1 stop13h 24mFrontier
Deal found 4/24$347
Cheap Chicago to Jamaica flights in April & May 2024
Find cheap flight options from Chicago to Jamaica specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,068,701 searches. Prices were last updated on April 25, 2024.
The lowest fares we've come across on flights traveling from Chicago to Jamaica in April and May 2024. Check back soon for alternative fares.
Sat 5/116:00 amORD - MBJ
1 stop9h 19mFrontier
Wed 5/158:32 amMBJ - ORD
1 stop8h 55mFrontier
Deal found 4/24$231
Sat 5/116:00 amORD - MBJ
1 stop25h 20mFrontier
Wed 5/158:32 amMBJ - ORD
1 stop8h 55mFrontier
Deal found 4/24$232
Sun 5/126:00 amORD - MBJ
1 stop7h 59mFrontier
Wed 5/158:32 amMBJ - ORD
1 stop8h 55mFrontier
Deal found 4/24$243
Thu 5/26:00 amORD - MBJ
1 stop25h 20mFrontier
Mon 5/63:34 pmMBJ - ORD
1 stop25h 53mFrontier
Deal found 4/25$255
Thu 5/26:00 amORD - MBJ
1 stop25h 20mFrontier
Thu 5/98:32 amMBJ - ORD
1 stop8h 55mFrontier
Deal found 4/25$256
Tue 5/76:00 amORD - MBJ
1 stop8h 53mMultiple Airlines
Fri 5/1012:45 pmMBJ - ORD
1 stop27h 50mMultiple Airlines
Deal found 4/25$257
Thu 5/210:17 pmMDW - MBJ
1 stop9h 03mFrontier
Mon 5/63:34 pmMBJ - MDW
1 stop27h 41mFrontier
Deal found 4/24$258
Sat 5/117:07 pmORD - MBJ
2 stops16h 34mMultiple Airlines
Wed 5/158:32 amMBJ - ORD
1 stop8h 55mMultiple Airlines
Deal found 4/24$271
Mon 5/136:00 amORD - MBJ
1 stop25h 20mMultiple Airlines
Fri 5/1712:45 pmMBJ - ORD
1 stop10h 44mMultiple Airlines
Deal found 4/24$275
Chicago to Jamaica 2024 flight deals
Discover exclusive flight deals for travel between Chicago and Jamaica in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,068,701 searches. Data last updated April 25, 2024.
The lowest fares we've come across on flights traveling from Chicago to Jamaica in April and May 2024. Check back soon for alternative fares.
Thu 5/210:17 pmMDW - MBJ
1 stop9h 03mFrontier
Mon 5/63:34 pmMBJ - MDW
1 stop27h 41mFrontier
Deal found 4/24$258
Wed 5/157:00 amMDW - MBJ
1 stop23h 57mFrontier
Sat 5/188:07 amMBJ - MDW
1 stop13h 29mFrontier
Deal found 4/24$281
Wed 5/87:00 amMDW - MBJ
1 stop24h 20mFrontier
Sat 5/1111:51 amMBJ - MDW
1 stop10h 50mFrontier
Deal found 4/24$282
Thu 5/910:17 pmMDW - MBJ
1 stop9h 03mFrontier
Sun 5/123:09 pmMBJ - MDW
1 stop23h 30mFrontier
Deal found 4/24$284
Thu 5/210:17 pmMDW - MBJ
1 stop9h 03mFrontier
Mon 5/63:34 pmMBJ - MDW
2 stops32h 42mFrontier
Deal found 4/24$287
Wed 5/157:00 amMDW - MBJ
1 stop23h 57mFrontier
Sat 5/188:07 amMBJ - MDW
2 stops16h 02mFrontier
Deal found 4/24$293
Fri 5/106:08 pmMDW - MBJ
2 stops43h 51mFrontier
Tue 5/148:32 amMBJ - MDW
1 stop10h 43mFrontier
Deal found 4/25$297
Fri 5/106:08 pmMDW - MBJ
1 stop16h 30mFrontier
Tue 5/148:32 amMBJ - MDW
1 stop10h 43mFrontier
Deal found 4/24$302
Wed 5/155:45 amMDW - MBJ
2 stops25h 12mFrontier
Sat 5/188:07 amMBJ - MDW
2 stops16h 02mFrontier
Deal found 4/24$304
Non-stop flights to Jamaica from Chicago
Discover non-stop flight options from Chicago to Jamaica. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 3,068,701 searches. Data last updated April 25, 2024.
To help reduce your travel time, choose from one of these non-stop flights from Chicago to Jamaica. Those looking to potentially save on 1 or 2-stop flights from Chicago to Jamaica should utilize the search form at the the top of the page.
Sun 7/78:45 amORD - MBJ
Nonstop3h 55mAmerican Airlines
Thu 7/112:05 pmMBJ - ORD
Nonstop4h 30mAmerican Airlines
Deal found 4/24$393
Sat 6/298:50 amORD - MBJ
Nonstop4h 05mAmerican Airlines
Thu 7/42:05 pmMBJ - ORD
Nonstop4h 30mAmerican Airlines
Deal found 4/25$443
Sun 5/199:10 amORD - MBJ
Nonstop4h 00mAmerican Airlines
Sun 5/262:05 pmMBJ - ORD
Nonstop4h 30mAmerican Airlines
Deal found 4/24$456
Tue 5/79:10 amORD - MBJ
Nonstop4h 00mAmerican Airlines
Fri 5/102:05 pmMBJ - ORD
Nonstop4h 30mAmerican Airlines
Deal found 4/25$458
Sun 6/168:45 amORD - MBJ
Nonstop4h 00mUnited Airlines
Fri 6/281:51 pmMBJ - ORD
Nonstop4h 24mUnited Airlines
Deal found 4/24$483
Sun 6/308:50 amORD - MBJ
Nonstop4h 05mAmerican Airlines
Sat 7/62:05 pmMBJ - ORD
Nonstop4h 30mAmerican Airlines
Deal found 4/25$493
Thu 7/48:50 amORD - MBJ
Nonstop4h 05mAmerican Airlines
Mon 7/82:05 pmMBJ - ORD
Nonstop4h 30mAmerican Airlines
Deal found 4/24$498
Sun 4/288:55 amORD - MBJ
Nonstop4h 05mAmerican Airlines
Tue 4/302:00 pmMBJ - ORD
Nonstop4h 35mAmerican Airlines
Deal found 4/24$499
Sun 5/268:45 amORD - MBJ
Nonstop4h 00mUnited Airlines
Sat 6/11:51 pmMBJ - ORD
Nonstop4h 24mUnited Airlines
Deal found 4/25$503
Chicago to Jamaica flights leaving soon
Find last-minute flight options from Chicago to Jamaica for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,068,701 searches. Data last updated April 25, 2024.
Check out these flights departing soon from Chicago to Jamaica. Users should examine the flight details to ensure there are no surprises.
Thu 5/210:17 pmMDW - MBJ
1 stop9h 03mFrontier
Mon 5/63:34 pmMBJ - MDW
1 stop27h 41mFrontier
Deal found 4/24$258
Wed 5/87:00 amMDW - MBJ
1 stop24h 20mFrontier
Sat 5/1111:51 amMBJ - MDW
1 stop10h 50mFrontier
Deal found 4/24$282
Thu 5/910:17 pmMDW - MBJ
1 stop9h 03mFrontier
Sun 5/123:09 pmMBJ - MDW
1 stop23h 30mFrontier
Deal found 4/24$284
Thu 5/210:17 pmMDW - MBJ
1 stop9h 03mFrontier
Mon 5/63:34 pmMBJ - MDW
2 stops32h 42mFrontier
Deal found 4/24$287
Thu 5/210:17 pmMDW - MBJ
1 stop9h 03mFrontier
Thu 5/98:32 amMBJ - MDW
1 stop12h 55mFrontier
Deal found 4/25$317
Tue 5/79:25 pmORD - KIN
1 stop14h 00mSpirit Airlines
Tue 5/1412:26 pmKIN - ORD
1 stop28h 09mSpirit Airlines
Deal found 4/25$328
Mon 4/296:55 amMDW - MBJ
1 stop24h 25mFrontier
Wed 5/13:34 pmMBJ - MDW
1 stop22h 19mFrontier
Deal found 4/25$334
Thu 5/212:42 pmMDW - MBJ
2 stops18h 38mFrontier
Mon 5/63:34 pmMBJ - MDW
2 stops49h 39mFrontier
Deal found 4/24$336
Tue 4/307:00 amMDW - MBJ
1 stop7h 53mFrontier
Tue 5/78:32 amMBJ - MDW
1 stop10h 43mFrontier
Deal found 4/25$340
One-way flights to Jamaica from Chicago
Search for one-way flight options from Chicago to Jamaica. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,068,701 searches. Data last updated April 25, 2024.
Take a look at some of the one-way flights we've detected from Chicago to Jamaica. Those seeking round-trip flights from Chicago to Jamaica should utilize the search form at the the top of the page.
Tue 5/146:00 amORD - MBJ
1 stop8h 53mFrontier
Deal found 4/24$99
Tue 5/147:00 amMDW - MBJ
1 stop7h 53mFrontier
Deal found 4/24$99
Thu 6/66:40 pmORD - KIN
1 stop16h 38mSpirit Airlines
Deal found 4/24$137
Sun 5/265:00 amORD - MBJ
1 stop6h 41mSpirit Airlines
Deal found 4/24$138
Sun 5/265:41 pmORD - MBJ
2 stops18h 19mSpirit Airlines
Deal found 4/24$151
Sun 5/262:33 pmMDW - MBJ
2 stops21h 27mMultiple Airlines
Deal found 4/24$171
Tue 5/149:10 amORD - MBJ
Nonstop4h 00mAmerican Airlines
Deal found 4/24$177
Mon 6/2411:26 amORD - MBJ
1 stop26h 02mFrontier
Deal found 4/23$180
Tue 4/305:00 amORD - KIN
1 stop6h 26mSpirit Airlines
Deal found 4/23$185
Find flights from Chicago to Jamaica within your budget
Customize your flight search to find flights from Chicago to Jamaica 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 3,068,701 searches. Data last updated April 25, 2024.
Fly from
Any airport
Fly to
Any airport
Budget
$328 - $510
Route
Depart
Return
Price
Chicago O'Hare IntlKingston Norman Manley
ORD - KIN
ORDKIN
Chicago O'Hare Intl
Tue 5/7
1 stop14h 00m
Kingston Norman Manley
Tue 5/14
1 stop28h 09m
$328
Chicago O'Hare IntlKingston Norman Manley
ORD - KIN
ORDKIN
Chicago O'Hare Intl
Tue 5/14
1 stop6h 25m
Kingston Norman Manley
Wed 5/15
1 stop11h 03m
$333
Chicago MidwayMontego Bay Sangster Intl
MDW - MBJ
MDWMBJ
Chicago Midway
Tue 5/21
1 stop22h 17m
Montego Bay Sangster Intl
Tue 5/28
1 stop13h 24m
$347
Chicago MidwayMontego Bay Sangster Intl
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 6/1
1 stop7h 42m
Montego Bay Sangster Intl
Tue 6/4
1 stop13h 24m
$348
Chicago O'Hare IntlMontego Bay Sangster Intl
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Wed 5/22
1 stop6h 41m
Montego Bay Sangster Intl
Thu 5/30
1 stop8h 21m
$352
Chicago O'Hare IntlMontego Bay Sangster Intl
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Thu 5/2
2 stops37h 24m
Montego Bay Sangster Intl
Thu 5/9
1 stop8h 55m
$359
Chicago O'Hare IntlMontego Bay Sangster Intl
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sun 7/7
Nonstop3h 55m
Montego Bay Sangster Intl
Thu 7/11
Nonstop4h 30m
$393
Chicago O'Hare IntlMontego Bay Sangster Intl
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Mon 6/17
1 stop17h 21m
Montego Bay Sangster Intl
Fri 6/28
Nonstop4h 24m
$488
Chicago MidwayKingston Norman Manley
MDW - KIN
MDWKIN
Chicago Midway
Fri 9/13
1 stop9h 36m
Kingston Norman Manley
Sat 10/5
1 stop8h 16m
$510
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Jamaica
Get insights into the airlines that provide service to Jamaica. 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 Jamaica. Reviews last updated April 25, 2024.
See what other customers who have flown with American Airlines, Frontier and Spirit Airlines from Chicago to Jamaica have to say. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
10,975 reviews
Boarding
8.2
Comfort
7.9
Crew
8.6
Entertainment
8.0
Overall
8.1
Food
7.4
Reviews
1 / 10
Terrible flight crew that skipped our row for service multiple times.
10,975 reviews
10,975 reviews
Boarding
8.2
Comfort
7.9
Crew
8.6
Entertainment
8.0
Overall
8.1
Food
7.4
Reviews
1 / 10
Terrible flight crew that skipped our row for service multiple times.
4,618 reviews
10,975 reviews
Boarding
8.2
Comfort
7.9
Crew
8.6
Entertainment
8.0
Overall
8.1
Food
7.4
Reviews
1 / 10
Terrible flight crew that skipped our row for service multiple times.
2,985 reviews
10,975 reviews
Boarding
8.2
Comfort
7.9
Crew
8.6
Entertainment
8.0
Overall
8.1
Food
7.4
Reviews
1 / 10
Terrible flight crew that skipped our row for service multiple times.
11,234 reviews
10,975 reviews
Boarding
8.2
Comfort
7.9
Crew
8.6
Entertainment
8.0
Overall
8.1
Food
7.4
Reviews
1 / 10
Terrible flight crew that skipped our row for service multiple times.
14,898 reviews
10,975 reviews
Boarding
8.2
Comfort
7.9
Crew
8.6
Entertainment
8.0
Overall
8.1
Food
7.4
Reviews
1 / 10
Terrible flight crew that skipped our row for service multiple times.
Related info for your journey
Find useful and relevant information for your journey from Chicago to Jamaica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to JamaicaSee prices for flight routes from nearby airports that may be better suited for you.
See prices for flight routes from nearby airports that may be better suited for you.
Top 8 airlines flying from Chicago to Jamaica
Discover the top 8 airlines that operate flights from Chicago to Jamaica. 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 3,068,701 searches. Data last updated April 25, 2024.
Search flights from Chicago to Jamaica by cabin class
Find flights from Chicago to Jamaica, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Hourly flight availability from Chicago to Jamaica
Find hourly flight availability from Chicago to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 25, 2024.
| 0%of flight departures | Early morningMidnight to 6 am |
|---|---|
| 100%of flight departures | Morning6 am to noon |
| 0%of flight departures | AfternoonNoon to 6 pm |
| 0%of flight departures | Evening6 pm to midnight |
Midnight
6 AM
Noon
6 PM
Book a flight to one of these trending destinations
User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
Fly with Cheapflights
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How does Cheapflights help users find flights from Chicago to Jamaica?
Cheapflights makes it easy to find Chicago to Jamaica flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.
Why should you use Cheapflights to find cheap flight tickets from Chicago to Jamaica?
Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Chicago to Jamaica for you. Better yet — we are completely free to use.
Can Cheapflights find flights from Chicago to Jamaica with no change fees?
Users can book flights with no change fees policies with our dedicated filters. Book flights from Chicago to Jamaica flexibly with Cheapflights today.
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Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!