Find cheap flights from Chicago Midway Airport to Jamaica

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MDW — Jamaica
Nov 5 — Nov 121
Round-trip
1 adult
Economy
0 bags
From?
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Sat 11/5
Sat 11/12

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Good to know

Low season

January

High season

June

Cheapest flight

$110

Average price round-trip

$686

Good deal round-trip

$686
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 18% increase in price.
Flight from Chicago Midway to Montego Bay Sangster Intl
(avg. price over the last 2 weeks)
or less

Top tips for finding cheap flights to Jamaica

  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be July and August. The cheapest month to fly to Jamaica is January.
  • Morning departure is around 49% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs - booking Jamaica flights

Top airlines flying Chicago Midway to Jamaica

Scores according to KAYAK customer reviews
7.9
DeltaOverall score based on 31510 reviews
8.1Boarding
7.8Comfort
8.5Crew
7.8Entertainment
7.5Food
Airline reviews

Delta didn’t completed the book, so let us behind half way

Read more about Delta

Delta didn’t completed the book, so let us behind half way

The plane was a little old so the quality of the glass for the windows were significantly degraded, making pictures on camera not translate well. I would suggest putting in new glasses for the windows on this aircraft.

From the check in crew all the way to onboard crew they were all great. Specially Diana at the boarding gate. She was amazing and she get smiling “thru her mask” even though the flight was delayed a little bit and people were starting to get stressed out. She was amazing.

The 2 hour delayed and the seats were very uncomfortable for economy

Cons: "The exit row door in 12B kept making a high pitch squealing noise...very unnerving"
Pros: "It was nice that the plane was not packed full."
Cons: "Box water instead of water bottles. The seat wasn’t very comfortable since it wouldn’t recline."
Pros: "Fly attendants have no knowledge of hospitality. They arguing with customers and refusing to assist, blaming on company policies. My friends were assigned seats next to a toilet. No folding options. One of our friends has a back pain problems and got stuck for 5 hours. There were seats available upfront and Manager Gina could simply change our seats instead of dry “there is nothing I can do” I am not recommending this airline."
Pros: "They left the bags at LAX. We we’re driving to Sun Valley and don’t have our ski clothes and equipment"
Cons: "Get our bags to us in the morning"
Pros: "Every was great, honestly"
Pros: "Nice crew"
Cons: "No leg room for 6’6” person."
Pros: "Flight was mostly uneventful, which is great! Right after takeoff we made a complete circle and no information was given as to why, but we assumed it was air traffic."
Pros: "These Comfort+ seats had the most legroom of any airline (Delta, JetBlue, American etc) short of Business class that I can remember in my adult life!"
Cons: "Add A Display Board For When Cabin Sections Are Boarding"
Cons: "More leg room and seat width. I don’t like having other passengers pressed against me."
Pros: "Nothing went wrong."
Cons: "We had a 5-hour layover in Atlanta. That was a bit long."
Pros: "Very smooth and friendly TSA personnel at the security point. Very friendly and respectful of the military. My husband is a Vietnam veteran."
Cons: "At least one hour late"
Cons: "Very late and boarded too long before leaving the gate."
Pros: "I liked the cookies and juice. The interactive screen to watch something. The cleanliness. The price. On time. The service. Thank you. The excitement of flying."
Cons: "The Wi-Fi cut out a bit"
Pros: "great service, easy to get on and off, snack options and drinks were all great"
Pros: "It is a short trip from Atlanta to Augusta."
Cons: "No complaints...too short of a trip to complain about anything!"
Cons: "No cookies"
Pros: "On time."
Pros: "Not much"
Cons: "Almost everything. The flight boarded late but quickly. We sat on the runway for hours. We were VERY delayed for RDU arrival. Luggage was slow in getting to baggage claim. Not enough help with baggage was available."
Pros: "The crew at the airport was very courteous and helpful."
Cons: "No food; not even offered water; I asked a Delta employee about our seats and she was very unprofessional (mind you I'm traveling with kids and my boarding pass said that seats were to be assigned at the gate)."
Pros: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos, please reimburse on the credit card"
Cons: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos of the studio and musicians"
Pros: "Wonderful plane, delicious food, great variety of drinks. Lots of movies to select from"
Cons: "Nothing"
Pros: "Nothing"
Cons: "Wouldn’t let us take our carry-on because they had overbooked and had no more room in overhead. Delayed our first flight and then our connecting flight left *early*. (If you know you have customers with short connections, why leave early to make their connections even shorter?) Then told us they would not pay for our hotel since it wasn’t their fault. Gave us a “discount” with a nearby hotel that was more expensive than what you could book it for online. Had to wait several hours for them to get us back the carry-on luggage that they insisted we check in the first place."
Pros: "Ice weather and flight cancelled, but they waited until the last minute to cancel it."
Cons: "Ice weather and flight cancelled, but they waited until the last minute to cancel it."
Pros: "There was a lot of food for this international flight. The seats were fine, just an overbooked plane."
Cons: "No complaints."
Pros: "My entire flight experience was delightful. Was dry impressed with the staff both at Hartsfield-Jackson and DFW...and our flight crew was positively sublime."
Cons: "My flight got delayed for twelve hours with no compensation for a hotel."
Pros: "Friendly crew"
Cons: "Long layover in Atlanta. Terrible terminal setup in LAX . Although we were on two connecting Delta flights, we had to leave the arriving terminal and take a bus to another. The second terminal (Terminal 2) was small, crowded, and had few food options."
Pros: "We were traveling with a toddler and infant but put in different row because the tickets were purchased separately. Gate staff promptly put us together and even bumped us up to delta comfort. Was a very pleasant trip. Thanks delta!"
Pros: "Two Delta agents a kiosk assistance were not aware of the Hurricane Irma policy of waiving baggage fees to my destination. I informed them that the website indicated it would waive baggage fees to certain destinations if checked in at the airport before a certain date. Another Delta agent nearby had to show them a copy of the policy before I could get my baggage fees waived."
Pros: "The food was excellent, as well as the flight attendants."
Pros: "The fact that there were no delays!"
Cons: "Nothing"
Pros: "I board sky priority or sooner so it always goes well."
Cons: "Delta could do a little more to align people behind the right zone pillars when lining up for boarding. Passengers especially those not used to flying or flying with Delta are always confused. Maybe some stripping on the floor could help or pillars at the front and midway back."
Pros: "Nothing"
Cons: "3.5 hour delay due to lack of co-pilot. No consessions for delay when asked at gate. Lack of leg room. Broken tv, I asked twice to be fix nothing was ever done."
Pros: "There were no problems at all, the only thing some times the entertainment would go out or slow, nothing else."
Pros: "Martha was wonderful"
Cons: "When I was transferred to Delta's website to book, the date was reset to 6 months in the future. It happened to be the same Monday the 26th so that's why I didn't notice. Delta refused to refund my money. This was a terrible experience and I plan not to use Kayak or Delta again!"
Pros: "Short eas6 trio"
Cons: "Lack if parking at airport"
Pros: "Hard to like anything with this delay -- missed 3 appointments in Raleigh."
Pros: "Left reasonably on time, arrived a bit early, able to find overhead storage for my roll-on, even boarding in Zone 3"
Cons: "Very tightly packed; minimal comfort for the flight."
Pros: "Flight attendant was excellent and pilots did a great job with weather"
Cons: "nothing."
Cons: "Seat back entertainment was outdated and non functional. Drinks were served but not a pretzel or peanut to be seen unless you were in first class."
Pros: "Enough said"
Pros: "The crew was nice"
Cons: "I didn't like the fact that I didn't get my luggage with me when I arrived to casablanca as I lived 4 hours away from the casablanca. I have to come back the next day to get my luggage. I was very mad about it.plus I noticed one of my luggage has been damaged so now I have to buy another one because I can t use it. It was disgusting."

It was canceled, and because of that, I lost two days of work.

The trip late more than 1 hour and gate change. The trip with reasonable price but everything is so poor. And they try to make extra money for anything

Pros: "Price. You get what you pay for"
Cons: "Why does the city have to fix a ramp? Leaving Denver was late arrived in Houston late. Cant get off plane due to equipment issues."
Cons: "Fix the plane before it’s scheduled to take off"
Pros: "Crew was ok. That’s about the only positive."
Cons: "Flight was late and delayed!! Bag drop wasn’t open early and when they did show up, didn’t seem to have it together. Really tired of Frontires incompetence!! Always late, delayed or Cancelled!! Lawn Chair seats are ridiculous and should be able to recline a bit. The seats they have are just cruel!!!!!! Not a bargain when you have to pay for bags, and slightly less uncomfortable seats! I’m done!"
Pros: "the quickness of the flight and the polite attendants"
Cons: "turbulence, but that isn't controllable"
Pros: "Flight was on time, got my seat assignment on arrival and scored an exit row seat. Perfect choice for a "shuttle" flight from COS to PHX."
Pros: "Excellent flight. Would absolutely go again"
Cons: "3$ for soda?"
Pros: "Staff was all great from boarding to inflight service"
Cons: "Na"
Pros: "The flight was smooth and arrived early."
Cons: "The seats were extremely uncomfortable. After 30 minutes, it felt like you were sitting on ply-wood. Seats did not recline at all. No leg room. Flight attendants stayed to themselves during the flight and seem to do the absolute minimum. Luggage retrieval took forever."
Pros: "On time"
Cons: "The food wasn't free on the airline"
Pros: "Smooth boarding. No issues in flight."
Cons: "Tiny tray tables; really couldn't utilize them for anything."
Pros: "The staff that handled baggage was nice. Also, I liked that we made it safe."
Cons: "My flight was supposed to leave at 3:50...I got to the airport and went through security before I found out that my flight was delayed until 7:30. The flight kept getting pushed back. I waited 8 hours before the flight took off. There no outlets anywhere...leaving customers at a disadvantage because with our delay, our electronics were all almost dead or dead. There were no food options. We were supposed to get a voucher, and I have not received it. Lastly, after waiting over 8 HOuRS, we still had to pay for snack and drink. I was ripped off and will not be flying with Frontier again."
Cons: "Flight attendant was sleeping during landing...pictures to prove it.."
Pros: "Poor service"
Cons: "Poor service"
Cons: "They give your only water"
Pros: "Crew was lovely, service was great, flight on time. The ladies at the gate were efficient and friendly."
Pros: "I'll give a thumbs up to a pleasant crew each flight, however, tho both flights were nonstop, both were very late to leave and tho the pilot said he'd make up time going east, that didn't happen and no apologies/explanations. To exacerbate the length of time traveling, both flights baggage retrieval were an hour. Add to that the really ridiculous hour long wait on the runway after landing because a gate wasn't available! Overall Frontier is pretty bad-they obviously do not employ enough people nor implement plans for staying on time or at least working to minimize delays due to weather issues. I have always left late on frontier but succumbed for the last time for a cheaper priced nonstop; it was definitely not worth it. To be clear about judging the length of time: flight out was scheduled to leave 1030 mountain and arrive 400 eastern. It was 630 eastern before we had our bags. Return flight was scheduled 500 eastern departure and 600 arrival mountain. It was 1000 mountain by the time we got our bags. One last comment-there were hundreds of unclaimed bags surrounding the frontier carousel...wonder where they were actually supposed to be???"
Pros: "Eparted and arrived close to bring on time....."
Pros: "Despite the hour we spent waiting on the tarmac for a gate to open, my flight to Denver, out of Cleveland, actually took place. I had a seat and everything!"
Cons: "I had a direct flight on Wednesday, the 21st of December, from Denver to Cleveland via Frontier. We arrived on time, checked our bags, and were given tickets that did not include seat assignments. Frontier oversold our flight by more than 30 seats! We were told that we might be able to make it home on Christmas if we flew Frontier, or we could make our own arrangements and Frontier would reimburse us up to $400. So, we wound up flying Delta from Denver to Minnneapolis, and then Minneapolis to Detroit, and then renting a car from Detroit to Cleveland. That got us home at about midnight, and cost us more than $600. It was the cheapest option available."
Pros: "Nothing."
Cons: "Flight was cancelled and I was told my only option was to wait 5 days or take my money back. Frontier refused to help me get on another airline to get to my destination. So I end up with a $150 refund and a last minute flight that costs me $600. Terrible customer service. Any other airline would've put me on another flight. never using Frontier again!!"
Pros: "arrived in timely manner"
Cons: "these seats and the tray tables are such a joke. frontier is so low quality. we want something comfortable to sit on so we can try to sleep"
Pros: "Te erything was fine"
Cons: "No complementary beverages"
Pros: "Boarding was smooth. Because Frontier charges per carry-on, it seems that most people check their bags rather than trying to cram carry-ons into overhead bins. This results in a smoother boarding process. The crew was professional and competent. Comfort wise, Frontier planes seem to have more leg room than other airliners."
Cons: "I'm not sure if it was Atlanta Airport's or Frontier's fault, but it took us about an hour after landing to pick up our checked baggage—ATL is undergoing construction, so there was a long walkaround, and the bags took a long time to show up at the carousel. The crew could have made less announcements and turned the cabin lights off sooner (this was a redeye flight). Comfort wise, Frontier seats seem to be less padded than in other airlines, and some seats do not recline."
Pros: "Good seating"
Cons: "After the $40 per bag (even as small as a purse) the ticket price ended up not being such a good deal."
Cons: "Airplane not clean. No entertainment at all."
Pros: "The plane ride was fast"
Cons: "The seats sucked, the flight attendants were rude. It was a very uncomfortable ride"
Pros: "Stewardess was funny."
Cons: "Everything else."
Cons: "$80 dollars in hidden fees, they charge for cary on, and there was no indication of that when i purchased my ticket"
Pros: "Arrived at destination alive."
Cons: "Flight took twice as long as expected due to repairs and weather issues. Comfort level was on the low side."
Pros: "Can't beat the price."
Cons: "Smooth flight but uncomfortable seating"
Pros: "Flight was on time and courteous staff"
Cons: "The flight was delayed by an hour but there was no announcement made"
Pros: "Honestly at first I liked how it appeared to be a newer plane with updated seats but then..."
Cons: "I saw those updated seats and the joke of a tray table that was provided wouldn't even hold my iPad. The staff was apparently new because they couldn't get through one intercom conversation without fumbling through it and when a customer asked how long the flight was the flight attendant didn't know and another passenger had to answer. We were delayed by 2 hours and all because the intercom phone was broken. I know it's a safety hazard but it just wasn't a smooth professional staff that you typically see. One of the three flight attendants was tenure but all I saw was the new girl fumble through everything. I'm hoping she was new...also, we are delayed two hours sitting on the plane, so I know people will give bad reviews about that but there's nothing you can control regarding our safety. It is what it is, I just couldn't stop shaking my head everything they spoke on the intercom how bad they were on it."
Pros: "cheap, clean, flight itself was fine"
Cons: "cramped, spent like 90 minutes on the tarmac"
Pros: "Disappointed that ticketing agent wouldn't let me check my bag since I was there before 45 minute deadline. Had to throw out my new shampoo and conditioner. Seats didn't recline for all nighter. Cheap, safe and on time."
Cons: "The plane was over 2 hours late, putting our arrival at after 1 am. This made post flight transportation a problem."
Pros: "The lady who checked me in, in Orlando, was awesome. She really seemed to care about my needs. She should get 5 stars!"
Cons: "We were suppose to take off from gate 12 at 7:55pm. They changed it to gate 13, & we didn't take off until almost 10:30pm. NO explanation was given!!"
Pros: "flight staff"
Cons: "OUTBOUND - confusion for me and others as gate changed and we had to go to international for domestic flight - thought it strange to suggest I pay additionally for a seat and a carry on. RETURN - again confusion for me and others as gate changed and no gate personnel at kiosk for quite awhile They don't even give a pretzel snack on these flights."
Pros: "Nothing"
Cons: "8pm flight progressively delayed until 3am on outbound Ord to Den leg THen on return 7 pm flight delayed until 11:30pm on Den to Ord leg With kids this was absolute misery"
Pros: "I like how frontier waited until I had driven three hours to the airport to tell me the flight was canceled and when I got there they couldn't even open their own computer system to give me information of a useful variety."
Cons: "I didn't like how I wasn't able to fly anywhere. My flight was cancelled and the next flight wasn't until three days later. Needless to say the next time I travel I would rather ride a blind three legged donkey than fly with frontier."
Pros: "Not much"
Cons: "Plane was 1.5 hours late. Seats are terrible. Charge for everything."
Pros: "Very informative on where to go!"
Cons: "Not very informational on security policy"
Pros: "I was not aware that both carry on AND checked bags incur a charge with Frontier. The only positive thing about this is that Frontier charges more to carry on a bag than to check a bag, so at least boarding was fast because most people checked their bags."
Pros: "The crew"
Cons: "I didn't know I didn't have assigned seating, had to pay additional fees for seats, not just once but for both planes on the same destination. I used to fly every couple of months to Denver and frontier airlines have changed their seats. They're very cheaply made and uncomfortable. Cheap and uncomfortable."
Pros: "Price, window seat."
Cons: "nothing"
Cons: "As with most planes, they need to spread the seats out to give us people with long legs more leg room. With a 3 plus hour or more flight, there should be movies available."
Pros: "price of ticket"
Cons: "charging for carry on"
Pros: "Smooth flight, on-time, good crew."
Cons: "Had to pay for a reclining seat. Had to pay for luggage. No food. Had to pay for tomato juice (really!)"
Pros: "I traveled from PHL to MBJ for $200 right in the middle of Christmas. Other airlines were charging $400 to $900 for a ticket. I didn't have that much money to waste so I was happy to see Frontier. I've never heard about Frontier but I said what the hell we're going to die one day anyway. On departure day everything went smoothly. I paid $160 for several bags. I didn't mind because I am used to travelling US Airways and American so bags weren't free with them either and Frontier's prices are a bit less for the first 2 checked bags. I was surprised about the carry on bag charge but everything still worked out to being less than what other airlines were charging. My flight left on time, arrived early and everything was good. I'm in Jamaica!"
Cons: "I don't see the need to charge to choose a seat but if that's how you keep your prices low I don't mind being assigned a seat. When your budget is low you have to compromise."

Book cheap flights from Chicago Midway Airport to Jamaica

Recent round-trip flight deals

12/3Sat
1 stopFrontier
13h 24mMDW-MBJ
12/8Thu
1 stopFrontier
15h 06mMBJ-MDW
$260
11/14Mon
1 stopFrontier
24h 09mMDW-MBJ
11/17Thu
1 stopFrontier
14h 37mMBJ-MDW
$266
12/3Sat
1 stopFrontier
13h 24mMDW-MBJ
12/8Thu
1 stopFrontier
15h 06mMBJ-MDW
$273
12/10Sat
1 stopFrontier
13h 24mMDW-MBJ
12/15Thu
1 stopFrontier
15h 06mMBJ-MDW
$274
12/5Mon
1 stopFrontier
24h 58mMDW-MBJ
12/8Thu
1 stopFrontier
15h 06mMBJ-MDW
$278
11/1Tue
1 stopFrontier
5h 58mMDW-MBJ
11/6Sun
1 stopFrontier
20h 40mMBJ-MDW
$283
10/27Thu
1 stopFrontier
21h 37mMDW-MBJ
11/4Fri
1 stopFrontier
22h 09mMBJ-MDW
$285
12/3Sat
2 stopsFrontier
17h 04mMDW-MBJ
12/8Thu
1 stopFrontier
15h 06mMBJ-MDW
$287
10/29Sat
1 stopFrontier
20h 08mMDW-MBJ
11/4Fri
1 stopFrontier
22h 09mMBJ-MDW
$293
12/3Sat
2 stopsFrontier
17h 04mMDW-MBJ
12/8Thu
1 stopFrontier
15h 06mMBJ-MDW
$297
11/1Tue
1 stopMultiple Airlines
5h 58mMDW-MBJ
11/9Wed
1 stopMultiple Airlines
9h 22mMBJ-MDW
$342
1/21Sat
1 stopMultiple Airlines
17h 28mMDW-MBJ
1/25Wed
1 stopMultiple Airlines
10h 43mMBJ-MDW
$347
11/5Sat
1 stopMultiple Airlines
14h 20mMDW-MBJ
11/12Sat
1 stopMultiple Airlines
9h 22mMBJ-MDW
$348
11/24Thu
2 stopsMultiple Airlines
19h 32mMDW-MBJ
11/29Tue
1 stopMultiple Airlines
27h 31mMBJ-MDW
$365
10/25Tue
1 stopMultiple Airlines
5h 58mMDW-MBJ
10/29Sat
2 stopsMultiple Airlines
15h 09mMBJ-MDW
$368
11/3Thu
2 stopsMultiple Airlines
15h 11mMDW-KIN
11/7Mon
1 stopMultiple Airlines
28h 13mKIN-MDW
$400
11/17Thu
1 stopMultiple Airlines
27h 16mMDW-KIN
11/20Sun
1 stopMultiple Airlines
21h 21mKIN-MDW
$420
1/8Sun
1 stopDelta
8h 26mMDW-KIN
1/17Tue
1 stopDelta
8h 22mKIN-MDW
$488
2/3Fri
2 stopsDelta
10h 19mMDW-KIN
2/7Tue
2 stopsDelta
8h 58mKIN-MDW
$492
1/8Sun
2 stopsDelta
10h 45mMDW-KIN
1/17Tue
1 stopDelta
14h 56mKIN-MDW
$563

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Recent one-way flight deals

10/25Tue
1 stopFrontier
5h 58mMDW-MBJ
$110
11/1Tue
1 stopFrontier
5h 58mMDW-MBJ
$115
10/29Sat
1 stopFrontier
20h 08mMDW-MBJ
$119
10/31Mon
1 stopFrontier
23h 28mMDW-MBJ
$122
1/28Sat
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17h 28mMDW-MBJ
$123
2/11Sat
1 stopFrontier
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$125
10/22Sat
1 stopFrontier
20h 08mMDW-MBJ
$126
11/13Sun
1 stopFrontier
27h 16mMDW-KIN
$127
12/9Fri
1 stopFrontier
24h 58mMDW-MBJ
$128
10/27Thu
1 stopFrontier
21h 37mMDW-MBJ
$129
10/29Sat
1 stopFrontier
20h 08mMDW-MBJ
$130
11/5Sat
1 stopMultiple Airlines
25h 49mMDW-KIN
$171
10/31Mon
2 stopsMultiple Airlines
17h 32mMDW-MBJ
$184
10/29Sat
2 stopsMultiple Airlines
18h 21mMDW-MBJ
$189
11/13Sun
1 stopMultiple Airlines
20h 13mMDW-MBJ
$199
11/20Sun
2 stopsMultiple Airlines
14h 15mMDW-MBJ
$202
10/29Sat
3 stopsMultiple Airlines
17h 32mMDW-MBJ
$205
11/12Sat
2 stopsDelta
10h 33mMDW-KIN
$209
11/3Thu
2 stopsMultiple Airlines
15h 11mMDW-KIN
$224
12/29Thu
1 stopDelta
14h 19mMDW-KIN
$336

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Chicago Midway Airport - Jamaica Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Jamaica - Chicago Midway Airport

Cabin classes:

$1,860
$686

Browse destinations: