Find cheap flights from Cayman Islands to Chicago Midway Airport

Find cheap flights from Cayman Islands to Chicago Midway Airport

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport. Bundle your flight + hotel and save!

Round-trip
Economy
Washington (WAS)
Chicago Midway
Tue 10/19
Tue 10/26
Any month
Bundle with KAYAK |
Include hotels

Top tips for finding cheap flights to Chicago Midway Airport

  • Looking for cheap airfare to Chicago Midway Airport? 25% of our users found tickets to Chicago Midway Airport for the following prices or less: From George Town $544 round-trip
  • High season is considered to be January, February and December. The cheapest month to fly to Chicago Midway Airport is January.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago Midway Airport flight deals.

FAQs - booking Chicago Midway Airport flights

How far is Chicago Midway Airport from central Chicago?

What is the name of Chicago’s airport?

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

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

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

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago Midway Airport?

Top airline flying Cayman Islands to Chicago Midway

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 29,957 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Cons: "Love delta. Everything was excellent"

Pros: "I appreciate the care Delta has for their passengers during this pandemic. From the seat spacing to the boarding process great measures were taken."

Pros: "Crew was very nice, professional."

Pros: "Crew was great"
Cons: "Lots of screaming children. Not much to be done about that."

Cons: "The Anchorage airport was FREEZING cold and it was August, maybe a little less AC IS IN ORDER"

Pros: "The crew was pleasant and helpful."
Cons: "The plane was an outdated jalopy. I thought the exit doors were going to fly off. This was in vast contrast to the 737 plane that we had taken earlier in the day for a flight from BNA to ATL."

Pros: "Predictably late."
Cons: "Be on time."

Pros: "Helpful crew. Arrived early."
Cons: "Plane was cold. Entertainment system didn't navigate very easily and choices seemed fairly limited on this (older?) plane."

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

Pros: "Friendly crew."
Cons: "Tight plane and late!"

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

Pros: "Attendants, food and entertainment very positive"
Cons: "Seats reserved online no where in system. Everyone seemed to be in zone 3 or at least decided to stand in line."

Pros: "Friendly and cheerful!"

Pros: "Everything was great except for the man that smoked in the restroom on the flight to Atlanta."
Cons: "A man smoked in the restroom on the flight to Atlanta, and I didn’t see ANY kind of repercussions for his endangering all of our lives. I would’ve very much liked to see him detained for the remainder of the flight."

Pros: "see above"

Cons: "The comfort seats are not that comfortable"

Pros: "The movies kept my daughter busy."

Pros: "Crew was good, plane was clean. We left on time and got in a bit early."
Cons: "Don't like the Comfort plus seats that have the dividers vs basic arm rests. TSA is a JOKE, got the random strip search where they pulled apart every nook and cranny of my personal bag and carry on item. Relieved me of my PLASTIC corkscrew that I've traveled with for 15 years. Almost missed the flight and I was there plenty early."

Pros: "In-flight entertainment Nice crew"
Cons: "The Delta seat assignment and boarding process The flight was delayed"

Pros: "Leg room and seats are very tight and I'm a small person."
Cons: "Coach class is very crowded."

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: "Wi-Fi on the plane is a nice touch."
Cons: "The seats are packed so tight there's almost no leg room - actually there is no leg room when the person in front of me reclined their seat. Since we were advised to get there 3 hours in advance only to wait two and a half hours in what is quite possibly the most uncomfortable waiting room anywhere this just makes the cramped plane even more frustrating."

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"

Pros: "My wife’s and my headphone connections would not work."

Pros: "Friendly service"

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: "The flight was great, the food really tasty and really nice plane."
Cons: "Standing in line for 5 hours without knowing what I'll be able to do. My entire body still hurts!"

Pros: "How can airlines help screaming children?"
Cons: "Screaming child on plane for 30 minutes have me a headache- perhaps flight attendants could offer something like coloring books or stickers to help in the future. When I got too baggage claim the baggage claim not listed. Ticket agents declined to help, so I was walking all over try g to find which claim area to go to which was frustrating."

Pros: "Arriving in 2 hrs from Orlando to laguardia!"
Cons: "no tv .. I didn't like that we had to use our own electronic device to access the entertainment system."

Cons: "Flight delayed. Had to hurry to get to my train."

Pros: "Airline stewards were very friendly and pleasant."
Cons: "We booked with Delta, but were put on Air France. Even though we had our boarding passes in hand we had to wait in long, slow line for baggage tags because they would not print from kiosk. There was minimal Air France staff on duty serving thousands of passengers during busy season (July). While the lines grew larger, the staff was reduced from 4 to 2. Another long, slow line for customs, another long slow line for security=Charles De Gaulle airport was awful. We arrived at the airport 4 hours before our departure time and got to our boarding gate with no time to spare."

Pros: "Delta has always be a step above the rest. Traveling with my children is not a problem and frowned upon with Delta. I rarely choose competitive airlines and will continue to use Delta as much as possible."

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: "Cabin crew were excellent and so friendly and down to earth."
Cons: "The seats are very hard but I find this with all the airlines now"

Pros: "On time great staff"
Cons: "Little cold"

Pros: "red"
Cons: "red"

Pros: "We got almost an absurd amount of food and drink on the flight, which was great. A meal, two snacks, a bottle of water, and several passes of the drink cart. The flight staff were all great, the entertainment options were plentiful. Really just a great flight."
Cons: "The Amsterdam airport was ludicrous. We were making a connection and had to go through four different levels of security. Our 1hr45minute layover was completely taken up just waiting in random lines to have someone look at our passports, or ask us to pull up our full flight itinerary email (teh boarding pass was not enough for her....). I appreciate the security attempts but it was really over the top, and the staff had no idea what they were doing (were bad at directing people to the right place or explaining what they needed). Note that NONE of this was the fault of Delta or KLM, completely teh airport."

Pros: "Great service"

Pros: "you must be kidding me!!! nothing to say good about this fly !!The sad part I'm American Express Delta SkyMiles credit card holder and they couldn't do anything for meThe only good thing we arrive in Mexico"
Cons: "flying to Mexico with. my two boys !!to begin I have to call Delta to put us seat together because the time of the fight had changed!! before we are siting by de middle of the plain when a booked r three seat together !! but than i got a imail confimatin with separete seattle for the kids!!we end up sitting all the way back on the plan!! we end up sitting all the way back on the plane l!! no TVs no windows in the last sits by the only two bathrooms on the plane with two boys that was not fun at all !!The sad part I'm American Express Delta SkyMiles credit card holder and they couldn't do anything for me when I called them"

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."

Pros: "Everything was smooth. Short flight, but they offered us refills on drinks, which I've never experienced before. Polite staff, great flight. Thanks!"

Pros: "The staff was great. The plane was the cleanest of MD-88s I'd been on recently."
Cons: "The old plans have your too cramped or squeezed in. The connecting flight from ATL to MKE made this one look good."

Pros: "On time, great service"

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)."

Cons: "The process of checking was very poor. One line was serving all of the Delta flights. Agents were very slow. Even when they started to serve my flight with priority still no impruvment. The agent who served me was so lost that he could not find the page with my picture and name in my passport!!!"

Pros: "Clean, and ultimately fine. Ultimately unremarkable."
Cons: "The agent at check-in was a little cranky, the lack of food (even for purchase) is disappointing, can't seem to spare more than the little cup of soda for beverages. No power in seats, so why use the wifi on battery? Ultimately fine though, just no amenities. We got where we were going on time."

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."

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Cayman Islands to Chicago Midway Airport

Airlines flying from Cayman Islands to Chicago Midway Airport 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 Cayman Islands to Chicago Midway Airport

Mandatory masks

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

Social distancing seating

Middle seats unavailable to book on flights from Cayman Islands to Chicago Midway Airport

Pre-flight testing

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

Book cheap flights from Cayman Islands to Chicago Midway Airport

Recent round-trip flight deals

1/14
Fri
2 stops
Delta
19h 56m
GCM - MDW
1/18
Tue
2 stops
Delta
25h 49m
MDW - GCM
2/8
Tue
1 stop
Delta
20h 53m
GCM - MDW
2/11
Fri
2 stops
Delta
41h 45m
MDW - GCM
2/8
Tue
2 stops
Delta
27h 16m
GCM - MDW
2/11
Fri
2 stops
Delta
45h 43m
MDW - GCM

Search by stops

Search by airline

Recent one-way flight deals

2/23
Wed
1 stop
Delta
23h 07m
GCM - MDW
2/24
Thu
2 stops
Delta
27h 55m
GCM - MDW
2/22
Tue
1 stop
Delta
23h 07m
GCM - MDW
2/25
Fri
1 stop
Delta
24h 12m
GCM - MDW
2/25
Fri
2 stops
Delta
33h 18m
GCM - MDW
2/26
Sat
2 stops
Delta
33h 18m
GCM - MDW
2/26
Sat
1 stop
Delta
9h 07m
GCM - MDW
Show more results
-
1
  • Round-trip
  • One-way
  • Multi-city
  • Trip Builder
  • Economy
  • Premium Economy
  • Business
  • First
  • Multiple
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First