Find cheap flights from Caribbean Islands to Chicago Midway Airport

Find cheap flights from Caribbean Islands to Chicago Midway Airport

Round-trip
Economy
Washington (WAS)
Chicago Midway
Tue 3/2
Tue 3/9
Any month
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Good to know

Low season

May Best time to beat the crowds with an average 10% drop in price.

High season

August Most popular time to fly with an average 21% increase in price.

Average price round-trip

$602 (avg. price over the last 2 weeks)

Good deal round-trip

$468 or less

Good deal one-way

$145 or less

FAQs for booking Caribbean Islands to Chicago Midway Airport flights

Which airlines have a flexible cancellation policy for flights from Caribbean Islands to Chicago Midway due to COVID-19?

How does KAYAK find such low prices on flights from Caribbean Islands to Chicago Midway Airport?

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What is the Hacker Fare option on flights from Caribbean Islands to Chicago Midway Airport?

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Top airline flying Caribbean Islands to Chicago Midway

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 29,036 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Cons: "Not a thing!"

Pros: "Cabin crew was great. Was told they don’t feel they can do a good job of serving 48 passengers in Premium Select with 2 crew."
Cons: "Image recognition step slowed boarding down a lot. Food and amenities on Delta Premium Select seem to be getting worse"

Pros: "Great flight attendants and service. Plenty of entertainment selection to make the long flight enjoyable. The boarding was chaotic because of the airport facility."
Cons: "The airport is too small for loading a full international flight."

Pros: "Fast service and precise timing"

Pros: "Great comfortable seats"
Cons: "Crowds in airport"

Pros: "Comfort is excellent"
Cons: "When traveling with the pet, personally always travel to Puerto Rico, we take our cat, I would like Delta to have the option of making the reservation online until paying for it, although you should always call to confirm, that would be super excellent."

Pros: "Nothing exceptional stands out"
Cons: "Flight was not on time"

Pros: "Clean plane. On time"

Cons: "They have to improve the boarding process a bit."

Pros: "Smooth ride"
Cons: "Seating"

Pros: "Flights were both timely"
Cons: "WiFi on flight from Atl to Tallahassee wasn’t working at first"

Pros: "Amazing service from crew"

Pros: "The entertainment"
Cons: "Space between"

Pros: "I missed my flight and you guys helped me catch the next one :D I was able to still make it yo my final destination within the same day"

Pros: "On flight entertainment was very good. Flight was smooth and ran ahead of schedule."
Cons: "They were out of vegetarian meal options. Really poor for a six hour flight. Also, the family behind us was atrocious, but that’s not Delta’s fault."

Cons: "Was refused to use the 1st clas restrooms but 10 minutes layer the flight attendant allowed an older gentleman and a lady to use them. I was in 10A with my service dog"

Cons: "Bigger personal space"

Cons: "No room to move very cramped"

Pros: "see above"

Pros: "Excelent flight excelent service.."
Cons: "The entrance in the gate to the plane always disorganized"

Pros: "My flight from STX was delayed some 30 minutes. That made a dent in the 57 minutes I had to catch my Delta flight. Naturally we landed at gate A2 and Delta was boarding at Terminal 2 gate B9. Me with my knee replacement can’t run and my wheelchair was not in sight. Thank goodness I had a carryon with wheels. I was out of breath when I got to Delta and the last passengers were boarding. I started panicking and interrupted the ground steward who asked me to wait with a smile. I waited . So when I told them I was standby they waved me on after showing my passport. I couldn’t find my boarding pass. I was pleasantly surprised to get a seat in first class. I was so thankful. My first time. Good things come to those who wait! Thank you Delta."

Cons: "Entertainment system wasn’t working"

Pros: "I like the fact that entertainment and technology is always good."
Cons: "Boarding is always a horrible experience. I never know what zone is boarding. Your agents at the gates are overwhelmed with so many things."

Pros: "Service was great, crew was responsive, snacks were good per usual."
Cons: "The AC was blasting at an all time high, felt frozen to my seat, even asked for a blanket but “ they didn’t have any more “, had to tuck in my arms into my layered shirt. this was a morning flight and no breakfast was served ... they didn’t even have food available for purchase."

Cons: "N!A"

Pros: "Nothing"
Cons: "Flight delay 5+ hours poor Service"

Cons: "The bulkhead sears had no electrical outlet"

Cons: "Flight delayed 2 hrs"

Pros: "After almost every airline cancelled. Delta still took me to where I needed to go with not one single problem. That pilot was amazing. I forget his name. But the plane didn't slide or anything during take off. Amazing."
Cons: "What was there not to like. We were a little bit late but I wasn't in a rush. I planned well ahead. Delta moved my flight from 10 a.m. to 6 a.m. and that was perfectly fine with me."

Pros: "Was initially hoping to fly a US airline but will now look for Aeromexico first. Exceeded my expectations!"
Cons: "The layover in Mexico City was a bit long and the airport was not so great"

Cons: "Cancel my flight at 7:50 am to 1:50pm"

Pros: "Boarding, checking in etc. The usual stuff, nothign spectacular."
Cons: "Seats are getting too crowded!"

Pros: "The crew was beyond friendly and courteous. Lots of leg room."
Cons: "I was an older plane, it was louder than our flight down to Atlanta. Nothing they could do about it, but a slight annoyance."

Pros: "Everything. I really loved that I could track where my checked luggage was, so when I arrived to my final destination I knew my bag was going to be there. The individual TV for my seat, so I could watch what I wanted. Having an USB port to charge my devices."
Cons: "Liked everything."

Pros: "No hubo retraso y salió todo el vuelo a tiempo. El personal fue atento."
Cons: "El espacio entre asientos es mínimo y es súper incómodo. La experiencia fue de incomodidad."

Pros: "Friendly and informative flight attendants kept the passengers in reasonable spirit."
Cons: "Left nearly an hour late after confusion related to oversold seats and upgrades. The gate agent entered the plane multiple times. The landing was rough, the brakes were loud."

Pros: "In flight entertainment interface and options were great!"
Cons: "Very uncomfortable!! Spent the entire flight with my knees pressed against the seat pocket. One flight attendant was somewhat rude and unpleasant."

Cons: "I don't know why delta's service has deteriorated so much in the last few years. Last two times that I flew the service and attitude at the gate has been horrible. Seat assignment has become a dread. Upgrade options are over priced. I guess I will be looking for a new airline."

Pros: "Everything"

Pros: "The crew was friendly and accommodating, and service was good"
Cons: "I purchased a basic economy ticket and upon checking in, my Delta app said my seat was unassigned and I had to get my boarding pass at the airport. I checked back later and the app had me as number 7 on the standby list. I called Delta (wait time 3+ hours... my flight was in 3), and then the Delta app support where I was able to get through to someone. She told me that the ticket I purchased over a month in advance did not guarantee me a seat on the plane (???). She said that if I was bumped from the flight they would reschedule me for the next morning. She was pretty rude and made it seem like I had a 50/50 shot of getting on this plane. I rushed to the airport in hopes that I would be the first from Standby there, and the gate agent told me that I was fine and would board right after first class and be assigned a seat then. Great. Once I got my seat assignment, I board to find out there is someone else sitting in my seat...... They eventually called the desk and had her moved, but it was the weirdest boarding experience I've had.. and I've flown Spirit. These planes that Delta fly's are SO OLD. Both times I have flown Delta the "turbulence" has been so bad and cold air was blowing right on my the whole flight with no option to turn it off (it wasn't from one of the vents, but from the side). Someone close to me works for Delta and I know for a fact that some of their engines blow mid-flight.. and they tell the passengers that it's turbulence.. so that doesn't make me feel very safe. I won't fly Delta again if there is another comparable option."

Cons: "Headphones suck"

Cons: "Flight attendants were a little snobby and didn't treat all passengers equally, in my humble opinion (note: I was sitting in 1st class)."

Pros: "The plane was surprisingly comfortable. The seats had USB ports. The touch screens were clear and responsive. Most importantly, the service of the flight attendants was excellent. I was quite happy."

Pros: "Always have great experience with Delta flight attendants and staff. The entertainment on mobile phone was a really nice add-on, I had never seen before."
Cons: "Flight was delayed in taking off, waiting for connecting passengers. Plane was old, which is most Delta planes, but this one showed it. The tray table looked like it was from the 70s or 80s. Flying into Midway instead of O'hare was anticlimactic."

Pros: "The onboard entertainment system was awesome.seats were comfortable."
Cons: "Flight was a bit bumpy."

Pros: "The gate agent was very helpful."
Cons: "The seat was very tight because the person who was next to me leaked over the arm rest into my space. I had a window seat. Also I had a torn ACL and requested a seat with more leg room and it was not assugned."

Pros: "Great Delta crew at check in and boarding!"
Cons: "Rear of plane very hot after passing through a very cool front. Service without a smile. "Don't have that" monitors on seats were almost useless."

Pros: "The pilot did a good job flying considering the conditions."
Cons: "Delta and Midway airport did not handle the weather conditions as well as they could have. Communications we terrible and no one adapted quickly to handle things properly. Of course the winter weather alert was mostly to blame, but what could be done to smooth things out didn't happen."

Pros: "Very easy going"

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Caribbean Islands to Chicago Midway

Airlines flying from Caribbean Islands to Chicago Midway 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 Caribbean Islands to Chicago Midway

Mandatory masks

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

Social distancing seating

Middle seats unavailable to book on flights from Caribbean Islands to Chicago Midway

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Caribbean Islands to Chicago Midway

Book cheap flights from Caribbean Islands to Chicago Midway Airport

Recent round-trip flight deals

5/19
Wed
1 stop
Delta
11h 01m
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5/23
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Delta
8h 23m
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8h 41m
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4/19
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3/18
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8h 23m
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7/14
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7/28
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8h 23m
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5/4
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5/9
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38h 36m
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27h 49m
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Recent one-way flight deals

3/10
Wed
1 stop
Delta
7h 31m
SJU - MDW
4/14
Wed
2 stops
Multiple Airlines
51h 28m
SJU - MDW
3/9
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Multiple Airlines
47h 45m
SJU - MDW
4/20
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8h 31m
SJU - MDW
4/17
Sat
1 stop
Delta
8h 10m
SJU - MDW
4/15
Thu
2 stops
Multiple Airlines
31h 53m
SJU - MDW
3/16
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2 stops
Multiple Airlines
46h 50m
SJU - MDW
5/24
Mon
1 stop
Delta
11h 01m
SJU - MDW
3/26
Fri
2 stops
Multiple Airlines
53h 28m
SJU - MDW
4/18
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2 stops
Multiple Airlines
31h 53m
SJU - MDW
4/21
Wed
2 stops
Multiple Airlines
46h 16m
SJU - MDW
4/20
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Multiple Airlines
35h 01m
SJU - MDW
3/20
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3 stops
Multiple Airlines
40h 49m
SJU - MDW
4/13
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Multiple Airlines
44h 36m
SJU - MDW
3/6
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37h 49m
SJU - MDW
5/24
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2 stops
Multiple Airlines
13h 16m
SJU - MDW
3/30
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1 stop
Delta
8h 15m
SJU - MDW
5/22
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1 stop
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9h 00m
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3/10
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7h 48m
PUJ - MDW
8/23
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2 stops
Delta
19h 12m
PUJ - MDW
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