Find cheap flights from Chicago Midway Airport to Jamaica

Find cheap flights from Chicago Midway Airport to Jamaica

Round-trip
Economy
Chicago (MDW)
Jamaica
Fri 1/22
Fri 1/29
Any month
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Good to know

Low season

November Best time to beat the crowds with an average 4% drop in price.

High season

May Most popular time to fly with an average 19% increase in price.

Average price round-trip

$605 (avg. price over the last 2 weeks)

Good deal round-trip

$568 or less

Good deal one-way

$459 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 January, November and December. The cheapest month to fly to Jamaica is August.
  • Morning departure is around 13% 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

How long is the flight to Jamaica from Chicago Midway?

Are there Jamaica travel restrictions currently due to Coronavirus?

How does KAYAK find such low prices on flights to Jamaica?

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Jamaica?

What is the Hacker Fare option on flights to Jamaica?

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Top airlines flying Chicago Midway to Jamaica

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 28,921 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Cons: "It was great fir a short flight. And they got me there early."

Cons: "Great flight. We were delayed but the crew kept us well informed and tried to make up time in the air"

Pros: "We got earlier than expected to our destination"
Cons: "Perhaps educate passengers on the new Delta process of boarding. Too many passengers where disorganized; the crew tried very cars to direct people"

Cons: "Not cancelling our flight"

Cons: "More leg room and seat width. I don’t like having other passengers pressed against me."

Pros: "Awesome Customer Service"
Cons: "Nothing"

Pros: "That I arrived safe."
Cons: "My seat didnt recline my back was in a lot of pain so was my neck. After getting to L.A at 9:52 a.m didn’t get out of the plane till 11:05 then the baggage claim was noted on carousel 2 when in fact it was carousel 3 when I asked a worker she said “I dont know ma’am” waved me off and kept walking. Terrible."

Pros: "Food Getting moved to the exit row for the extra leg room"
Cons: "Didn’t like having to wait so long to book my seat and ended up on the back row the worst seats on the plane"

Cons: "At least one hour late"

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."

Pros: "Food and entertainment were non-existent since the flights were so short and on smaller jets.....so I guess 1star isn't really fair, but there was no option for N/A Flight attendants were friendly. VPS-ATL lead attendant was very sweet to a passenger in front of us who was on her first flight alone with her child to go to her fathers funeral in the Philippines. She also thanked a soldier for her service. Love these little touches."
Cons: "I'm so used to the nice screens with free tv games and flight tracker and really missed that on this trip. I'm glad I decided not to pay to upgrade to comfort + this trip for the first time in a long time."

Pros: "left on time and arrived early"
Cons: "no legroom even in first class."

Pros: "The plane left on time and arrived on time."
Cons: "I did not like the fact that the food they served made my child sick. But hey, that is a given. Most airplane food sucks. But it shouldn't make a person sick. The flight staff was okay, but not nearly as professional and friendly as the crew flying to Lisbon. Thankfully none of them ran over my foot with the metal cart."

Cons: "Boarding was a little bit rushed and the gate agent was visibly irritated by some passengers who didn’t check their bags."

Pros: "Everything was perfect and most of all ON TIME Thank you Delta!"

Cons: "Flight was delayed with no explanation, The crew sprayed me twice with the fizz from opening soda cans with no apology."

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: "I liked that the plane wasn’t full which was a surprise."
Cons: "Last leg of the flight as usual we had some plane on it’s last legs with entertainment equipment from the 90’s and that’s being generous. My iPhone 7Plus is only a little smaller than the screen they would have you watch for five hours. Also the plane was old and noisy and seats were not really comfortable. But this is par for the course flying to Hawaii for some reason, no matter the carrier. Hawaiian Airlines is usually better but that’s to be expected."

Pros: "liked the pods in delta one"
Cons: "wish the pods were a little longer for sleeping. it your 6'1 or taller you can't completely stretch out"

Pros: "every person who was not a delta employee, those people were kind and helpful."
Cons: "The gate agent was the opposite of professional. You might as well get a cardboard cutout. The gate agent was unable or unwilling to explain when and how I would get my seat assignment and with what group I should board with. A passenger helped me. I am a frequent flyer, primarily AA, I will never fly Delta again."

Pros: "The free TV was nice."
Cons: "A tiny bag of pretzels is a stingy snack. Aeromexico gave us a croissant with two pieces of cheese,applesauce and a square of chocolate."

Pros: "I love Delta, especially their newer planes that have screens in the backs of headrests and free movies."
Cons: "Leg room is never enough. I'm 6'1"."

Pros: "Everything was delightful on Delta’s side. Very comfortable. Great service."
Cons: "Why do parents with infants choose to sit in First Class. Crying babies are not appreciated when I’ve paid a lot of money for a First Class experience. The parents in the sears behind me had a child who cried & cried. It was a real spoiler for me. I enjoyed eveeeythinf about the First Class experience except that."

Cons: "My seat was taken by another person and the crew member was not very helpful with getting the issue resolved"

Pros: "Smooth take off and landing"
Cons: "N/A"

Cons: "Gate attendant was extraordinarily rude"

Cons: "could not check in on line as you did not give us the confirmation of the carrier we used which was not west jet the one you booked us through. You need to fix this problem for us to use you again"

Pros: "great staff . clean. current movies"
Cons: "n/a"

Pros: "The boarding was very organised and the crew very friendly. The snacks that they offer is great too"

Pros: "Crew was very helpful."
Cons: "Food was terrible and check in can be more organized."

Pros: "All the staff are sincere in serving. It must be a direct result of the great management at the top. If the employees were unhappy and rude that also would be a direct reflection of the management. I use the same flight often and let the staff know I appreciate them."
Cons: "Snacks are small, but delicious cookies."

Pros: "I liked the fact that I was able to watch a movie on my phone."
Cons: "The flight was very rough at times."

Pros: "Hey, domestic U.S. flights aren't all bad! I was pleasantly surprised by the kind service and amenities on this Delta flight. There's a plethora of free movies to watch, and the crew continually checked on us to make sure we were hydrated. I think Delta may become my new prefered carrier for domestic flights."
Cons: "Bathroom ran out of toilet paper, but staff helped fix this after I talked with them."

Cons: "The flight was OK."

Pros: "Friendly staff, good service in First Class. Had the side with only one seat -- nice to have no neighbors."

Pros: "Movies"
Cons: "Seats are in humane"

Pros: "Great experiencing getting on and off the plane"
Cons: "Nothing"

Cons: "Excellent service excellent pilot"

Cons: "Got stuck for two hours sitting in the plane because the computer systems went down."

Pros: "the flight was on time and the staff very helpful"

Pros: "I liked the fact that they have a train to take you from one concourse to another!"
Cons: "Very busy airport! Boarding was delayed and flight was overbooked. I wasn't too happy but it could've been worse."

Pros: "Small cubicles are pretty comfortable but a little cramped . No they are upgrading their business class to larger "suites" and that will be good . The food is good but nothing to write home about . Your payment system works well but as usual there is a somewhat limited library."

Pros: "None"
Cons: "I was separately seated from my husband and had to seat in the middle because my ticket status was economy"

Cons: "Not enough water on the flight and we landed in a parking lot and shuttled back to the airport."

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."

Cons: "There were many empty seats, and when I moved from a cramped seat to a fully open row, the attendant rudely and humiliatingly admonished me for moving to a comfort+ from my "preferred" seat. It was unprofessional and extremely uncalled for. The seats were completely empty and there was no reason for him to admonish me loudly and rudely. I suffer from severe general anxiety disorder, fur which I take appropriate medications, but this incident caused an anxiety attack that lasted through the rest of the flight. Extremely disturbing that crew would behave so rudely and insensitively to anyone."

Pros: "same"
Cons: "same"

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."

Pros: "Boarding was fast."

Pros: "The washrooms"
Cons: "Entertainment. There was none! The seats could have been more comfortable"

Pros: "Roomie seat. Professional curdious crew. Fast smooth flight. Westjet connect access for entertainment."

Cons: "One of the crew members seemed really bother by everything. She was not smiling or even looking at customers when handing drinks over."

Pros: "Crew were very caring. Seats were OK"

Pros: "The food"
Cons: "The staff insisted on putting bags underneath seats for a 13 hours flight..."

Cons: "The boarding process is terrible. One line for section 2,3,4 causes so much chaos."

Cons: "Flight delay so far 2 hours"

Pros: "for that price I'll fly west jet every time"
Cons: "some water or something was falling from the ceiling on my brother in the window seat on take off at the back of the plane was pretty gross"

Pros: "The entertainment"
Cons: "The yelling on the airport intercoms"

Pros: "Direct flight"
Cons: "Screaming crying children"

Pros: "The crew was exceptional..service was implacable .was my 2 year old son first time flying..sns6he was in awe...the ladies made him feel loved and welcome."

Pros: "Punctuality and smooth flight"

Pros: "Westjet team is fast, nice and solve issues in one call. I have had very good experiences with westjet! Thank you!"
Cons: "Today in Montreal during boarding the lady coordinating did not give priority to people with children. We were at leastthree families - we were all upset with the situation. However as I have had very good experiences with west jet I consider this an isolated issue."

Pros: "Left on time or mighty close to it. Arrived on time. Safe and mostly smooth flight. Flight attendants and pilot was friendly. Liked the price for a direct flight."
Cons: "Tight squeeze in the seats in terms of having the back of the passenger in front of you right in your face practically."

Pros: "The ease of boarding with very nice staff!"

Cons: "The flight was 5 hours 40 min late The Flight attended (her name was if not mistaken Staysy or start with S) was staying at the door as a security guard in a detention center without formal greeting “welcome on board”, no smile at all and later jumped on me regarding my bag. I was seated when her collage pulled my back bag from the compartment to make room for a bigger luggage, left it on the seat next to me and said will take care later. With frustrating tone Staysy showed up and command me to put it under the seat. I told her to put it under and not to command me with this tone... as it was not my decision the bag to be there. She did put it under but kept making comments and even did not apologize. A frustrating flights - over 5 hours late with spicy flight attendant attitude."

Cons: "Original flight was cancelled . Re booked on a different flight , that one was delayed with no new time , with a threat that that flight would be cancelled , we were booked on a 3rd flight , to Toronto to connect to a delta flight to Atlanta . We were told that delta would give us our boarding pass to Atlanta at the delta desk in Toronto. At delta in Toronto we were advised that there were no available seats on the flight we were supposed to be booked on . Delta booked us to Detroit then on to Atlanta . Trip delay was over 9 hours and lots of stress and run around . Very disappointed with west jet . We have always used west jet and this was the first time we felt we were given very poor service .causing a very long and stressful day , arriving at our destination 9 hours later than planned , resulting in a 24 hour exhausting travel day."

Cons: "Flight delayed 2 hours, missed connectionplus an hour on the tarmac"

Pros: "very nice staff. comfortable seats"
Cons: "no ice for drinks. would have preferred in flight entertainment on seat backs"

Pros: "No comments"
Cons: "Everything"

Pros: "impressed with Westjet"

Pros: "I received adequate notification for check in and updates"
Cons: "There was a slight delay though we managed to arrive on time"

Pros: "Staff and aervice was great! No complaint!"
Cons: "We had to put our carry on bags a little far away from our seats"

Pros: "The flight was not cancelled in spite of poor weather"
Cons: "Flight on tarmac for 2 hours after loading passengers no word regularly from pilots or anyone for a long time. Baggage loading and no accountability for huge delays for lost luggage containers? Who is the logistics team? This is not the first time westjet has provided poor service on their international flights. Training if ground staff onsystems is poor. He guest services at tronto openly claimed they did lot know how to operate certain screens for transactions."

Pros: "Honestly, I slept on my flight so I miss all the perks. I’d assume everything was fine since they let me sleep. They also let me board early since my foot was in a cast."
Cons: "Flight was delayed, but not by much."

Pros: "Nothing"
Cons: "Everything"

Cons: "Waiting at Toronto airport from 8 oclock to 11 oclock pm"

Pros: "Friendliness of staff"
Cons: "Had an aisle seat but was disturbed 4 times throughout the flight. Not impressed"

Cons: "ran out of food only had 10 tablets to offer customers on a packed plane"

Pros: "Order ahead food was easy and selection was tasty"
Cons: "Bring a book! Apps to have your entertainment on individual devices is a bad idea."

Pros: "Friendly Staff"
Cons: "Flight delayed departing but pilot made up the time ."

Cons: "Pre-ordered meals are costlier than those purchased on board. The crew explains it by saying that they give some extra food just before landing, in lieu of that but what they give is too meagre and its not the customers choice."

Cons: "Rough landing and held up the taxiway for an hour"

Pros: "Cabin crew was nice"
Cons: "always delayed. not very accommodating with cancelled flights"

Pros: "I had 2 checked in bags, the charge a bit to high, When fly between Canada - USA, 1 allowable check-in luggage should be included in the fare. Please think about it."

Pros: "They brought the movie thingy out right away and managed to watch 2 movies made the whole trip thanks west jet"
Cons: "Always the food seems like every sandwich has cheese in it or sausages. Meat both have dairy and I have dairy allergies it makes it hard how about a good old tuna sandwich (not old) u just get a well made sticker and put it on the old menu"

Pros: "Flight attendants Snacks Entertainment options"
Cons: "No screens; but the options were provided"

Pros: "You pay for what you get. WestJet staff are always wonderful. The fligh is a flight."
Cons: "Was't a problem with WestJet. However if ever departing from Vancouver don't rely on the wait times provided in the airport. Give yourself ab addition 30 mins extra."

Pros: "Everything"
Cons: "No meal on the plane"

Pros: "I had a 5 month old baby and the crew was super smiley and friendly. Also, the flight wasn't full so there was plenty of room. I really enjoyed my experience. Thank you Westjet!"

Pros: "Only the boarding was good"
Cons: "My luggage was damaged"

Pros: "WestJet staff and crew fantastic"

Pros: "Luggage came fast. Car rental was great."
Cons: "Changed planes, changed seats after paying for advanced booking. Service was poor, cabin was hot."

Cons: "Good Choice of movies to watch on my tablet, but sound was really bad, worse than when i play my music from my tablet on the same earphones"

Pros: "Everything was great!!"

Pros: "Nothing"
Cons: "They had a gate delay making 30+ people miss their connection. Refused accomodations. Now we are stuck at the airport with no nearby hotels available and no transport for our final destination."

Pros: "Price, staff"
Cons: "Uncomfortable seats, no padding, very hard. At Pearson you have to walk about half an hour to get to West Jet gate."

Pros: "We got some extra help in the airport :). Thanx"

Cons: "It was as if the baggage fell of somewhere from the plane and came in contact with water."

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Chicago Midway to Jamaica

Airlines flying from Chicago Midway to Jamaica have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Chicago Midway to Jamaica

Mandatory masks

Masks required on board, masks provided on flights from Chicago Midway to Jamaica

Social distancing seating

Middle seats unavailable to book on flights from Chicago Midway to Jamaica

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Chicago Midway to Jamaica

Book cheap flights from Chicago Midway Airport to Jamaica

Recent round-trip flight deals

2/18
Thu
1 stop
Delta
7h 15m
MDW - MBJ
2/23
Tue
1 stop
Delta
7h 22m
MBJ - MDW
4/22
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Delta
8h 45m
MDW - MBJ
4/27
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Delta
10h 27m
MBJ - MDW
2/11
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1 stop
Delta
8h 57m
MDW - MBJ
2/15
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1 stop
Delta
18h 20m
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2/18
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1 stop
Delta
8h 57m
MDW - MBJ
2/21
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1 stop
Delta
8h 57m
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2/17
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Delta
24h 58m
MDW - MBJ
2/20
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Delta
20h 52m
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3/7
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Delta
17h 03m
MDW - MBJ
3/13
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Delta
10h 45m
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8h 57m
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7h 22m
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6h 05m
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24h 58m
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24h 15m
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5/7
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28h 52m
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Recent one-way flight deals

5/18
Tue
1 stop
Delta
6h 05m
MDW - KIN
2/18
Thu
1 stop
Delta
8h 57m
MDW - MBJ
5/20
Thu
1 stop
Delta
6h 05m
MDW - KIN
5/17
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Delta
9h 31m
MDW - KIN
5/26
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Delta
16h 49m
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5/23
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Delta
9h 31m
MDW - KIN
5/26
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Delta
8h 58m
MDW - MBJ
5/27
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2 stops
Multiple Airlines
21h 03m
MDW - KIN
5/21
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Delta
9h 31m
MDW - KIN
6/25
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Delta
11h 10m
MDW - MBJ
1/30
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Delta
5h 35m
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6/25
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Delta
9h 31m
MDW - KIN
5/27
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Multiple Airlines
40h 47m
MDW - MBJ
5/27
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Multiple Airlines
38h 28m
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5/27
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Delta
17h 03m
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6/17
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Delta
11h 10m
MDW - MBJ
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