Cheap Flights from Chicago to Montego Bay
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RatePunk searches hundreds of travel sites at once for deals on flights to Montego Bay
Prices updated 24 days ago
486,190 searches this week
171 airlines compared
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Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)
Today’s best flight deals from Chicago to Montego Bay
Explore current cheapest deals departing from Chicago to Montego Bay
Round trip
Sort by: Cheapest
September 19 - September 23
ORD - Montego Bay
$368
$342
Round trip
September 8 - September 11
ORD - Montego Bay
$365
$343
Round trip
September 19 - September 26
ORD - Montego Bay
$361
$343
Round trip
November 2 - November 5
ORD - Montego Bay
$437
$343
Round trip
October 25 - October 29
ORD - Montego Bay
$399
$353
Round trip
November 1 - November 11
ORD - Montego Bay
$427
$355
Round trip
November 1 - November 6
ORD - Montego Bay
$439
$358
Round trip
December 8 - December 11
ORD - Montego Bay
$489
$363
Round trip
October 18 - October 23
ORD - Montego Bay
$393
$364
Round trip
August 24 - August 28
ORD - Montego Bay
$388
$366
Round trip
Unlock all 500+ flight deals to Montego Bay and get alerts when great deals appear
Route Intelligence — 486,190 Searches this Week
Insights for flights from Chicago to Montego Bay
How much is a round trip from Chicago to Montego Bay
Regular price: $313 - $569
Prices for flights from Chicago to Montego Bay are currently within the regular range.
The regular price range for flights from Chicago to Montego Bay is $313 to $569. The current lowest deal is $342 with JetBlue Airways, for travel from September 19 to September 23.
now $342
Low $313
High $569
The cheapest time to fly from Chicago to Montego Bay
The cheapest month to fly from Chicago to Montego Bay is March, with a median price of $138. The most expensive month is August, with a median price of $1057. Prices are generally lower from January to December.
March
Flights from $138
August
Flights from $1,057
Direct flights from Chicago to Montego Bay
American Airlines
Last-minute flights going from Chicago to Montego Bay
Thu, Jun 18
MDW - Montego Bay
Chicago (MDW) - Montego Bay (MBJ)
Frontier Airlines
$696
$582
One-way
Thu, Jun 18
MDW - Montego Bay
Chicago (MDW) - Montego Bay (MBJ)
Frontier Airlines
$790
$586
One-way
Sat, Jun 20
MDW - Montego Bay
Chicago (MDW) - Montego Bay (MBJ)
Frontier Airlines
$791
$574
One-way
Wed, Jul 1
MDW - Montego Bay
Chicago (MDW) - Montego Bay (MBJ)
Frontier Airlines
$821
$534
One-way
Fri, Jul 3
MDW - Montego Bay
Chicago (MDW) - Montego Bay (MBJ)
Frontier Airlines
$754
$514
One-way
Sun, Jul 5
MDW - Montego Bay
Chicago (MDW) - Montego Bay (MBJ)
Frontier Airlines
$811
$473
One-way
Biggest price drops on these dates for flights from Chicago to Montego Bay
Jul 5 - Jul 8
$811 → $473
42%
Jul 12 - Jul 15
$771 → $472
39%
Jul 5 - Jul 9
$810 → $516
36%
Jul 1 - Jul 4
$821 → $534
35%
Popular Airports to fly from Chicago to Montego Bay
Chicago - Montego Bay route insights
💸 Price insights
Recent fares are above the typical level
Recent fares for Chicago to Montego Bay are above the typical level, with a median of $807.
📅 Best time to fly
Fly in March for the best prices
Historically, March offers the lowest median price at $138, followed by April at $436.
⏱️ Flight duration
Flights typically take 33h 17m
The median flight duration from Chicago to Montego Bay is 33 hours and 17 minutes.
✈️ Airlines & availability
Connecting flights are dominant
Only 14.3% of deals are direct, with connecting flights having a median of 3 stopovers.
🏆 Airline highlight
American Airlines offers direct flights
American Airlines is one of the carriers that historically offered direct flights on this route.
🎯 Booking tip
Deals appear frequently
Deals for this route appear frequently, with over 1 deal per day in a 30-day window.
Chicago main airports to depart from
O Hare International (ORD)
O'Hare International Airport offers flights to Montego Bay, with prices starting from $342.
📍 ~25 km from Chicago (reachable by car or train)
💸 Flights from ~$342
Chicago Midway International (MDW)
Chicago Midway International Airport is an alternative for flights to Montego Bay, with prices from $423.
📍 ~15 km from Chicago (reachable by car or train)
💸 Flights from ~$423
Chicago Rockford International (RFD)
Chicago Rockford International Airport provides another option for flights to Montego Bay, with prices from $506.
📍 ~120 km from Chicago (reachable by car)
💸 Flights from ~$506
Montego Bay main airports to arrive at
Sangster International (MBJ)
Fly into Sangster International for direct access to Montego Bay and surrounding Jamaican attractions.
📍 ~5 km from Montego Bay (reachable by car)
💸 Flights from ~$342
Airports nearby Montego Bay used as alternative
Norman Manley International (KIN)
Norman Manley International Airport is a major international gateway in Jamaica, offering a wide range of flights.
📍 ~135 km from Montego Bay (approximately a 3 to 4-hour drive)
💸 Flights from ~$436
Owen Roberts International (GCM)
Owen Roberts International Airport is the closest major international hub outside of Jamaica with strong connectivity.
📍 ~330 km from Montego Bay
💸 Flights from ~$430
Providenciales International (PLS)
Providenciales International Airport is a significant international airport with numerous premium flight options.
📍 ~600 km from Montego Bay
💸 Flights from ~$469
Lynden Pindling International (NAS)
Lynden Pindling International Airport is one of the largest and most popular hubs in the Caribbean.
📍 ~900 km from Montego Bay
💸 Flights from ~$318
Cibao International (STI)
Cibao International Airport is a large international airport in the Dominican Republic with high popularity.
📍 ~750 km from Montego Bay
💸 Flights from ~$404
Business & First Class Flight Deals to Montego Bay
Discover luxury on the budget with premium cabin class on flights from Chicago to Montego Bay.
Elite
Best Elite deals to Montego Bay
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From ORD
Elite
Jul 13
Montego Bay, Jamaica
87% AI deal score
$1,801
$961
Save $840
From ORD
Elite
Oct 28
Montego Bay, Jamaica
87% AI deal score
$2,038
$1,083
Save $955
From ORD
Elite
Aug 01
Montego Bay, Jamaica
85% AI deal score
$1,832
$1,091
Save $741
From ORD
Elite
Oct 29
Montego Bay, Jamaica
85% AI deal score
$2,001
$1,142
Save $859
From ORD
Elite
Sep 10
Montego Bay, Jamaica
85% AI deal score
$2,507
$1,610
Save $897
From ORD
Elite
Oct 25
Montego Bay, Jamaica
84% AI deal score
$1,655
$1,052
Save $603
From ORD
Elite
Aug 09
Montego Bay, Jamaica
84% AI deal score
$1,741
$1,057
Save $684
From ORD
Elite
Dec 02
Montego Bay, Jamaica
84% AI deal score
$1,890
$1,163
Save $727
From ORD
Elite
Dec 06
Montego Bay, Jamaica
84% AI deal score
$1,907
$1,166
Save $741
From ORD
Elite
Dec 08
Montego Bay, Jamaica
84% AI deal score
$1,916
$1,171
Save $745
From ORD
Elite
Oct 27
Montego Bay, Jamaica
84% AI deal score
$1,950
$1,173
Save $777
From ORD
Elite
Dec 06
Montego Bay, Jamaica
84% AI deal score
$1,937
$1,181
Save $756
From ORD
Elite
Dec 09
Montego Bay, Jamaica
84% AI deal score
$1,973
$1,186
Save $787
From ORD
Elite
Dec 09
Montego Bay, Jamaica
84% AI deal score
$1,940
$1,191
Save $749
From ORD
Elite
Sep 10
Montego Bay, Jamaica
84% AI deal score
$2,475
$1,607
Save $868
From ORD
Elite
Oct 01
Montego Bay, Jamaica
84% AI deal score
$2,403
$1,609
Save $794
From ORD
Elite
Oct 15
Montego Bay, Jamaica
84% AI deal score
$2,397
$1,609
Save $788
From ORD
Elite
Oct 01
Montego Bay, Jamaica
84% AI deal score
$2,437
$1,609
Save $828
From ORD
Elite
Sep 10
Montego Bay, Jamaica
84% AI deal score
$2,479
$1,610
Save $869
From ORD
Elite
Nov 03
Montego Bay, Jamaica
83% AI deal score
$1,554
$1,044
Save $510
From ORD
Elite
Dec 06
Montego Bay, Jamaica
83% AI deal score
$1,533
$1,044
Save $489
From ORD
Elite
Oct 28
Montego Bay, Jamaica
83% AI deal score
$1,581
$1,052
Save $529
From ORD
Elite
Oct 28
Montego Bay, Jamaica
83% AI deal score
$1,581
$1,054
Save $527
From ORD
Elite
Dec 14
Montego Bay, Jamaica
83% AI deal score
$1,544
$1,061
Save $483
From ORD
Elite
Nov 05
Montego Bay, Jamaica
83% AI deal score
$1,833
$1,166
Save $667
From ORD
Elite
Nov 08
Montego Bay, Jamaica
83% AI deal score
$1,838
$1,181
Save $657
From ORD
Elite
Nov 09
Montego Bay, Jamaica
82% AI deal score
$1,485
$1,042
Save $443
From ORD
Elite
Nov 16
Montego Bay, Jamaica
82% AI deal score
$1,509
$1,042
Save $467
From ORD
Elite
Nov 02
Montego Bay, Jamaica
82% AI deal score
$1,508
$1,044
Save $464
From ORD
Elite
Nov 08
Montego Bay, Jamaica
82% AI deal score
$1,514
$1,044
Save $470
From ORD
Elite
Nov 09
Montego Bay, Jamaica
82% AI deal score
$1,514
$1,052
Save $462
From ORD
Elite
Nov 17
Montego Bay, Jamaica
82% AI deal score
$1,509
$1,052
Save $457
From ORD
Elite
Nov 10
Montego Bay, Jamaica
82% AI deal score
$1,514
$1,052
Save $462
From ORD
Elite
Nov 03
Montego Bay, Jamaica
82% AI deal score
$1,515
$1,054
Save $461
From ORD
Elite
Oct 26
Montego Bay, Jamaica
82% AI deal score
$1,579
$1,083
Save $496
From ORD
Elite
Oct 27
Montego Bay, Jamaica
82% AI deal score
$1,623
$1,083
Save $540
From ORD
Elite
Oct 28
Montego Bay, Jamaica
82% AI deal score
$1,579
$1,093
Save $486
From ORD
Elite
Aug 06
Montego Bay, Jamaica
82% AI deal score
$1,808
$1,230
Save $578
From ORD
Elite
Oct 01
Montego Bay, Jamaica
82% AI deal score
$2,435
$1,724
Save $711
From ORD
Elite
Oct 22
Montego Bay, Jamaica
82% AI deal score
$2,409
$1,751
Save $658
From ORD
Elite
Oct 15
Montego Bay, Jamaica
82% AI deal score
$2,422
$1,751
Save $671
From ORD
Elite
Nov 11
Montego Bay, Jamaica
81% AI deal score
$1,474
$1,042
Save $432
From ORD
Elite
Nov 17
Montego Bay, Jamaica
81% AI deal score
$1,467
$1,052
Save $415
From ORD
Elite
Nov 04
Montego Bay, Jamaica
81% AI deal score
$1,472
$1,054
Save $418
From ORD
Elite
Nov 01
Montego Bay, Jamaica
81% AI deal score
$1,468
$1,054
Save $414
From ORD
Elite
Oct 27
Montego Bay, Jamaica
81% AI deal score
$1,655
$1,168
Save $487
From ORD
Elite
Oct 22
Montego Bay, Jamaica
81% AI deal score
$2,379
$1,724
Save $655
From ORD
Elite
Oct 15
Montego Bay, Jamaica
81% AI deal score
$2,380
$1,724
Save $656
From ORD
Elite
Nov 04
Montego Bay, Jamaica
80% AI deal score
$1,472
$1,074
Save $398
From ORD
Elite
Oct 22
Montego Bay, Jamaica
80% AI deal score
$2,424
$1,843
Save $581
From ORD
Elite
Oct 15
Montego Bay, Jamaica
80% AI deal score
$2,422
$1,844
Save $578
From ORD
Elite
Oct 22
Montego Bay, Jamaica
80% AI deal score
$2,423
$1,844
Save $579
From ORD
Elite
Sep 10
Montego Bay, Jamaica
80% AI deal score
$2,565
$1,907
Save $658
From ORD
Elite
Sep 10
Montego Bay, Jamaica
80% AI deal score
$2,475
$1,907
Save $568
From ORD
Elite
Sep 10
Montego Bay, Jamaica
80% AI deal score
$2,505
$1,907
Save $598
From ORD
Elite
Nov 11
Montego Bay, Jamaica
76% AI deal score
$1,473
$1,083
Save $390
From ORD
Elite
Nov 06
Montego Bay, Jamaica
76% AI deal score
$1,473
$1,096
Save $377
From ORD
Elite
Nov 06
Montego Bay, Jamaica
76% AI deal score
$1,489
$1,106
Save $383
From ORD
Elite
Nov 23
Montego Bay, Jamaica
76% AI deal score
$1,493
$1,126
Save $367
From ORD
Elite
Oct 28
Montego Bay, Jamaica
76% AI deal score
$1,579
$1,166
Save $413
From ORD
Elite
Oct 30
Montego Bay, Jamaica
76% AI deal score
$1,580
$1,166
Save $414
From ORD
Elite
Oct 25
Montego Bay, Jamaica
76% AI deal score
$1,579
$1,168
Save $411
From ORD
Elite
Oct 30
Montego Bay, Jamaica
76% AI deal score
$1,625
$1,176
Save $449
From ORD
Elite
Oct 25
Montego Bay, Jamaica
76% AI deal score
$1,623
$1,178
Save $445
From ORD
Elite
Oct 30
Montego Bay, Jamaica
76% AI deal score
$1,657
$1,208
Save $449
From ORD
Elite
Jul 17
Montego Bay, Jamaica
76% AI deal score
$1,785
$1,231
Save $554
From ORD
Elite
Jul 04
Montego Bay, Jamaica
76% AI deal score
$1,780
$1,255
Save $525
From ORD
Elite
Nov 26
Montego Bay, Jamaica
75% AI deal score
$1,448
$1,133
Save $315
From ORD
Elite
Nov 29
Montego Bay, Jamaica
75% AI deal score
$1,477
$1,168
Save $309
From MDW
Elite
Aug 13
Montego Bay, Jamaica
75% AI deal score
$2,089
$1,612
Save $477
From ORD
Elite
Oct 01
Montego Bay, Jamaica
75% AI deal score
$2,403
$1,907
Save $496
From ORD
Elite
Nov 18
Montego Bay, Jamaica
74% AI deal score
$1,466
$1,173
Save $293
From ORD
Elite
Nov 01
Montego Bay, Jamaica
74% AI deal score
$1,468
$1,176
Save $292
From ORD
Elite
Dec 07
Montego Bay, Jamaica
74% AI deal score
$1,537
$1,276
Save $261
From MDW
Elite
Aug 13
Montego Bay, Jamaica
74% AI deal score
$2,057
$1,658
Save $399
From MDW
Elite
Aug 13
Montego Bay, Jamaica
74% AI deal score
$2,069
$1,666
Save $403
From ORD
Elite
Nov 13
Montego Bay, Jamaica
73% AI deal score
$1,486
$1,256
Save $230
From ORD
Elite
Nov 09
Montego Bay, Jamaica
73% AI deal score
$1,474
$1,256
Save $218
From ORD
Elite
Nov 08
Montego Bay, Jamaica
73% AI deal score
$1,474
$1,259
Save $215
From ORD
Elite
Nov 11
Montego Bay, Jamaica
73% AI deal score
$1,485
$1,266
Save $219
From ORD
Elite
Nov 13
Montego Bay, Jamaica
73% AI deal score
$1,474
$1,266
Save $208
From ORD
Elite
Nov 22
Montego Bay, Jamaica
73% AI deal score
$1,493
$1,291
Save $202
From ORD
Elite
Oct 28
Montego Bay, Jamaica
73% AI deal score
$1,623
$1,375
Save $248
From ORD
Elite
Oct 31
Montego Bay, Jamaica
72% AI deal score
$1,580
$1,378
Save $202
From ORD
Elite
Dec 10
Montego Bay, Jamaica
72% AI deal score
$1,550
$1,381
Save $169
From ORD
Elite
Nov 07
Montego Bay, Jamaica
71% AI deal score
$1,475
$1,378
Save $97
From MDW
Elite
Aug 13
Montego Bay, Jamaica
71% AI deal score
$2,056
$1,911
Save $145
From MDW
Elite
Aug 13
Montego Bay, Jamaica
71% AI deal score
$2,089
$1,911
Save $178
From MDW
Elite
Aug 13
Montego Bay, Jamaica
71% AI deal score
$2,087
$1,912
Save $175
From MDW
Elite
Sep 10
Montego Bay, Jamaica
70% AI deal score
$2,175
$2,094
Save $81
From MDW
Elite
Sep 10
Montego Bay, Jamaica
70% AI deal score
$2,223
$2,123
Save $100
From MDW
Elite
Sep 10
Montego Bay, Jamaica
69% AI deal score
$2,094
From MDW
Elite
Sep 10
Montego Bay, Jamaica
69% AI deal score
$2,116
$2,094
Save $22
From MDW
Elite
Sep 10
Montego Bay, Jamaica
69% AI deal score
$2,123
From MDW
Elite
Sep 10
Montego Bay, Jamaica
69% AI deal score
$2,123
From MDW
Elite
Aug 19
Montego Bay, Jamaica
69% AI deal score
$2,280
From MDW
Elite
Aug 06
Montego Bay, Jamaica
68% AI deal score
$2,547
From MDW
Elite
Aug 06
Montego Bay, Jamaica
68% AI deal score
$2,547
From MDW
Elite
Aug 06
Montego Bay, Jamaica
68% AI deal score
$2,746
From MDW
Elite
Aug 19
Montego Bay, Jamaica
67% AI deal score
$3,248