Find cheap flights from Chicago Midway Airport to Montego Bay

MDW - MBJ

Find cheap flights from Chicago Midway Airport to Montego Bay

Round-trip
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Chicago (MDW)
Montego Bay Sangster Intl
Tue 11/24
Tue 12/1
Any month
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Good to know

Low season

November Best time to beat the crowds with an average 15% drop in price.

High season

May Most popular time to fly with an average 28% increase in price.

Average price round-trip

$662 (avg. price over the last 2 weeks)

Good deal round-trip

$568 or less

Good deal one-way

$459 or less

When to book flights from Chicago Midway to Montego Bay

Estimated round-trip price
Average price per month

Top tips for finding a cheap flight

  • Looking for a cheap flight? 25% of our users found flights on this route for $459 or less one-way and $568 or less round-trip.
  • High season is considered to be April, May and June. The cheapest month to fly is November.
  • Morning departure is around 11% 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 for booking Chicago Midway Airport to Montego Bay flights

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Top airlines flying Chicago Midway to Montego Bay Sangster Intl

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 28,783 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Pros: "Flight was fina s far as air travel goes today. If they are forcing taller people to pay extra for comfort they have succeeded as in the future I will have to look into "comfort plus. I am not large, 6'1" 180# and my knees were tight to the seat in front with my back tight into the seat. Not a great way to spend 4 hours!!!"
Cons: "Extra personal space and food that isn't served frozen would be nice!"

Cons: "It felt like the flight attendant had a long day. Chairs weren't super comfortable."

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

Pros: "Desk attendant was very helpful, personable, and efficient"
Cons: "Couldn’t get a boarding pass for the last leg of my trip (AZO>DTW>ATL>CSG) when I checked in online, couldn’t get it at the Delta counter in AZO, nor in DTW. The staff at the Delta counter in ATL resolved it in less than ten seconds."

Pros: "Awesome crew"
Cons: "More room"

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

Pros: "Amazing service and F&B offered was wonderful"

Pros: "Crew was wonderful! Food was good. It was a good experience."
Cons: "This whole paying for comfort seats is annoying. Just make all the seats decent for all travelers."

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

Pros: "Boarding was easy."
Cons: "I am 6' 1" tall and weigh 220, so not out of the ordinary and I felt like I was stuffed into a sardine can."

Pros: "They did get to reschedule me on both my flights, but lost my bag."

Pros: "Luggage plane to carousel at Atlanta way too slow"
Cons: "Smooth flight, more than average beverages serving; food fine. Seats too small."

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 was great. the plane was very comfortable and i also like the fact that there was free movies and wifi inside the plane"

Pros: "Short flight"
Cons: "Flight attendant was not willing to go above and beyond as he stated he would. My husband asked for a coke and the flight attendant told him he could only get water."

Pros: "El cumplimiento de vuelos"

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."

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"

Cons: "You messed up my life with your poor service."

Cons: "Delta scheduled us a connection with only 35 min of layover. We had to go from Concourse E to A and the plane was several min late.We barely made it before the gate closed 10 min before pushback."

Pros: "The crew and overhead storage."

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: "Every one was nice"
Cons: "No problems"

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

Pros: "I was not able to change seats..."

Pros: "Left early and arrived early."
Cons: "Smallest bathroom on a plane I've ever seen. Could barely sit down without my knees banging into door or wall."

Pros: "I liked the fact that the flight left on time and landed ahead of schedule."
Cons: "The flight was rough. The coffee was horrible though."

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

Cons: "Nothing"

Pros: "I got home safe"
Cons: "Plane delayed by over 3 hours and they told me to wait at the airport for 6 hours instead of arriving at the normal international flight arrival times. My day was completely wasted. They offered a replacement plane was old with tiny broken screens, broken seats. It smelled horrible as we were boarding from the tarmac. I'll never eat airplane food again."

Pros: "Entertainment"
Cons: "Staff were a bit rude. The boarding process was slow as everyone rushed up when they announced the first zone to board, and obviously this was not policed. We didn't get our seats until we got to the gate because apparently we bought our tickets too soon to take off, which was three weeks. Also, staff claimed there wasn't enough bin space so asked people to check their bags. We saw people with two big bags get on board at the start, and then staff made everyone at the back of the line check their bags. But there was plenty of bin space before take off. And we were seated in the last row which can't recline."

Pros: "It was on time. Flight crew was courteous. Plenty of room and comfy seats. Good entrainment media"
Cons: "Wish it would've had more movie options"

Pros: "Crew was excellent everything served was of great quality, all the amenities were solid and flight was comfortable and on time."
Cons: "The only complaint was the extreme use of air conditioning that made it a necessity to use many blankets to keep warm from freezing."

Pros: "Porsha. The best flight attendant ever. Not"
Cons: "Liked everything"

Pros: "The staff was was very accommodating to myself and my 19 month old daughter"

Pros: "Nice plane."
Cons: "No in flight TV."

Cons: "I thought I stated this before about the flight (5), Treatment (5) all the rest (5), but Atlanta Airport does not support disabled people using scooters to get from one plane to another. With more people using these, only a matter of time until a reporter males this an ISSUE. Meanwhile I will make every effort NOT to use ATLANTA HARTSFIELD. This includes my wife, also using a scooter."

Cons: "Ok. My wife and I are both disabled and use our own scooters to get around airports. My scooter broke down when I got off the plane. Toronto airport became a LOT longer pushing my scooter then. Fortunately CANADIANS GAVE ME A HAND TO GET THROUGH CUSTOMS, BAGGAGE CLAIM AND CAR RENTAL. Ok, what to do if something like this happens in America. Maybe to work with security staff cause I was in dire straights without the Canadians to help me. Thank them all. Alton Cason"

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: "No issue. Everything was good."
Cons: "Not much. Everything was good."

Pros: "Comfort with entertainment."
Cons: "No food options at all."

Cons: "After 600,000 miles of flying, this one was the worst. 5 hours on the tarmac for a 4 hour flight."

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: "The flight crew was nice and polite. They served drinks and snacks in a timely manner while on the flight."
Cons: "Flight was scheduled to leave early, the plane arrived, but they couldn't turn the plane around fast enough. We left the gat late, then pilot said we would still be arriving half an hour early. We arrived about 45 minutes late, and that was a problem because our connecting flight was due to depart now in 15 minutes. Lightning forced the airport to shutdown, which was great, we had a chance to catch our flight, but we were stuck in the airplane, and we couldn't get to our gate until the all-clear. I know this is not Delta's fault, but they did arrive quite late on a flight that, according to them, would be early. They also never communicated to the other flight that there were several passengers catching that connection. So by the time we had ran to catch our connection they had closed the ramp. Lightning hit again, and they shutdown the airport once again, so the airplane was still at the gate for about an hour, and they did not allow the 20+ passengers to board that plane, which was right there. So frustrating. The only thing that saved it was that our new flight was the new airbus, and although it left an hour and a half later, the comfort level was phenomenal."

Pros: "The crew was really fantastic the service was very good."

Cons: "The 2 hr delay for mechanical issue, having to board and then as soon as we left gate having to go back an deplane"

Pros: "Crew service was excellent"
Cons: "Poor leg space"

Pros: "All excellent"
Cons: "Snacks without caffeine"

Pros: "Crew were helpful"
Cons: "Everything was great"

Cons: "4 hour delay"

Pros: "The entire flight and crew were very kind and friendly"
Cons: "Better snack/meal option"

Cons: "Cramped seats entertainment"

Pros: "Every thing"
Cons: "Nothing"

Pros: "Larger size plein, comfortable seats and great Crew"
Cons: "Price"

Pros: "Nothing to be completely honest"
Cons: "Airplane was old and dirty. Flight attendants were extremely rude and condescending. The plane arrived nearly 3 hours late. Boarded 30 minutes late waited on the tarmac for an additional 2 hours while they performed maintenance. They ran out of food for what was now an 8 hour flight. Starving!"

Cons: "After landing, we were waiting on the tarmac for sometime and I needed to use the restroom I was an allowed to do so. It would’ve taken me a short short time. I went to The rear of the plane to use the restroom and was told to get in my seat."

Pros: "Crew was nice. Hard landing,cramped seats"

Cons: "More space, quicker boarding and getting off, and better transfers"

Pros: "The staff at the airport in Cancun are amazing! Wonderful service from the time you enter the terminal till you are checked in and through security. The flight on WestJet was excellent."
Cons: "Getting through YYZ is horrible. Two CBSA clerks checking the customs forms at the exit of the baggage area (twelve pickup areas). Really? Get a grip CBSA."

Pros: "The service was great!"
Cons: "A little bit delayed"

Pros: "organic bars, hot green tea in real mug, friendly staff"
Cons: "no entertainment or WiFi and seats did not recline."

Pros: "Very friendly and helpful staff at both baggage check-in and during flight. That is why I fly WJ."
Cons: "Leg room on plane."

Pros: "Prices of flights going to Calgary Canada"
Cons: "Prices did not include specific seat.. that was an additional price to pick a seat"

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: "Price"
Cons: "Head crew person was lazy and bad attitude. The rest were very good"

Pros: "I’m always impressed with the service on WestJet, and they didn’t disappoint on this flight. They were warm, courteous and hard working."

Pros: "The plane was clean, comfortable and the staff were good."
Cons: "WestJet was 30 minutes late to board. Also, if you're going Int'l during a peak moment, give yourself at least 2 hours to process your entry. It's crazy how many people are going thru JFK."

Cons: "I was told they don't help you store your carry on. At 66 and 5 feet tall this seems like an impossible feat likely to create issues as it falls on my head."

Pros: "Amazingly quick check in. Great and friendly customer service. Genuinely sincere."

Pros: "Crew were amazing"
Cons: "Loading was an absolute disaster, never seen it so slow before"

Pros: "Smiling staff. Very helpful"
Cons: "No complaints"

Cons: "Late landing, packed like sardines, couldn’t move my arms in my seat. Tried to choose seat in exit row for leg room but plane was changed so no leg room."

Cons: "Big 4 hour delay caused that we missed another flight in London"

Pros: "My first trip started on a poor note; I got to airport about an hour before boarding, only to find out that my flight was rescheduled from 9:30am to about 6:15pm ( or so) on that same day without prior notice. I went up to the counter and asked for confirmation for the switch and inquire if there was an issue, which may have affected my original flight. Turned out that the change was due to weather conditions at Toronto (makes sense). I had suggested that it would have been nice to receive some sort of notification, before starting that day way too early and inconvenience of going to pickup my car from the airport parking, only to come back again. The attendant sympathized with my plight and compensated me with a lunch voucher (which was nice of him and WestJet). Matter was resolved; I came back to catch my flight and the trip was wonderful :)"
Cons: "I didn't like the fact that my flight was rescheduled without receiving any notification from 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: "Honesty when informing us on our flight delay."

Pros: "Crew was very nice, a good selection of entertainment and comfortable seating."
Cons: "Having to wait in the plane for an hour prior to takeoff due to a lock issue with the washroom."

Pros: "Punctual departure. (Made my international connection in plenty of time)"

Pros: "It was nice staff r very friendly"

Pros: "Friendly staff."
Cons: "Delays. Canadian debit card not accepted on flights even though an American debit card was."

Pros: "Quick boarding, good customer service, and friendly staff."
Cons: "When I booked online it was a little unclear that I would have to pay extra to check a bag. No problem but would make a better customer experience if I had been aware of this"

Pros: "Crew overworked but pleasant and doing their best. Self check in works well with assistance"
Cons: "Management decisions meant assigned crew arrived after our flight supposed to depart. Needed 1 more person to service passengers. We waited a long time after serving started to get served. We did not know that food could be preordered online and served soon after takeoff. No TV screens on back of chairs...had to rent device to see movies. Have app but not able to book and get points. Wrote to WJ for help but oo response"

Pros: "I was a pleasant trip overall, no delays, everything went fine. I still would prefer built in screens but I watched a movie on my iPhone and it was ok."
Cons: "When we were boarding, I was supposed to give my little case for check in. I had gone through many hoops to make the carry on happen ( all cosmetics in little containers, restricted space overall) and then, just because I was in Zone three and all the spaces were taken, I had to hand in my suitcase. Suggestion: could the above space be reserved for the passengers who sit right underneath?"

Pros: "The granola as the in flight snack."
Cons: "There was not enough options if you wanted more water, or juice. There was not even a soda option available."

Pros: "inflight entertainment was good and friendly staff"
Cons: "lots or turbulence and uncomfortable landing"

Pros: "Crew was fun and helpful. Was extremely accommodating in helping me switch to an earlier flight"

Pros: "Crew was great. Flight was on time."
Cons: "This older plane had tiny seats in the seat backs. My phone screen was bigger. Thought we might get a meal on a flight of this length and at this time of day."

Pros: "Seats were roomy. The biscoff was tasty. No issues boarding or during the flight."
Cons: "The westjet app wouldn't let me sign in so no entertainment but I brought my own so no biggie. This flight was fully booked And they needed people to check their bags. One flight attendant seemed kind of snippy about it to another passenger but I understand her frustration."

Pros: "Efficient and Friendly Service. Clean Aircraft. Snacks and drinks."
Cons: "Window seat is very cramped due to curve of the aircraft. Effectively no room to stretch both your legs."

Pros: "The crew and staff were great on the plane. Could use more staff at the checked bags area but overall good experience"
Cons: "More agents at the check in desk"

Cons: "It's been more than 50 hours and I still haven't received both of my checked in luggage"

Pros: "Seamless boarding"

Pros: "Smooth, friendly and cost effective."

Pros: "Didn't like anything. Specially the fact that I left home at 3am and I'm still not in LA"
Cons: "THE DELAYS! 36 HOURS ON THE ROAD AND STILL GOING! NEVER AGAIN!!!!"

Pros: "NOTHING"

Pros: "Not often can you find good flight arrangements at a great price from WestJet but was very happy in this case. Seat selection is far better than other carriers and service, boarding was very seamless. Good Job WestJet!"

Pros: "They upgraded me to plus after my luggage was damaged on my 7 hour flight. If you can upgrade to plus do it!!"
Cons: "It was a great flight"

Read more about Delta

Book cheap flights from Chicago Midway Airport to Montego Bay

Recent round-trip flight deals

12/5
Sat
1 stop
Delta
9h 00m
MDW - MBJ
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WestJet
23h 49m
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12/9
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9h 00m
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Delta
17h 12m
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12/19
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14h 47m
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Multiple Airlines
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