Find cheap flights from Aruba to Chicago Midway Airport

Find cheap flights from Aruba 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
Boston (BOS)
Chicago Midway
Thu 12/9
Thu 12/16
Any month
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Top tips for finding cheap flights to Chicago Midway Airport

  • 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.

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Top airline flying Aruba to Chicago Midway

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 30,147 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Pros: "crew was amazing"

Pros: "Great crew."

Pros: "The crew was polite"
Cons: "Less delays"

Cons: "Food offered in first"

Cons: "Cramped seats, no a/c on tarmac for extended period because of technical issue, ancient entertainment system. Old plane with minimal overhead bin space, delayed flight"

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

Pros: "The crew was awesome. The entertainment was great with a huge selection of movies. The food was really good."
Cons: "Boarding was delayed while waiting for Delta agents to come and assist people off of the plane."

Pros: "you were on time !!"
Cons: "space between seats !!!"

Pros: "The male crew member was excellent. He was responsive and speedy with trying to find a solution. He gave me a few flyer miles for my trouble and was empathetic, which is rare."
Cons: "The tv/monitor didn’t work so there wasn’t any entertainment for the majority of the flight."

Pros: "The seat was very comfortable even as a basic seating and the entertainment options were great."
Cons: "The voice from the pilot was very loud and would be too much if I had my headphones on."

Cons: "I understand when weather is rough not moving the beverage carts but a small bottle of water would be appreciated."

Pros: "see above"

Pros: "The flight was not crowded and plenty of flight attendants offering service throughout flight Also smoo5h flight."

Pros: "Had a great experience with Delta all around. Seating and crew were lovely, in flight entertainment was great. Overall, very pleasant experience and flight was on time."

Pros: "The service is very good from the beginning. The flight attendant is very caring thanks so much."

Pros: "Quick flight"
Cons: "Nothing"

Pros: "Friendly"

Pros: "The staff & crew were friendly. I liked having access to free entertainment. I liked being able to see the tracking of my checked bag (notifications)."

Pros: "Staff was attentive and pleasant. Seat was comfortable, good knee room. Left and arrived on-time. Good experience."
Cons: "Reclining seats need to either go away, or be built so that reclining takes leg room away from the person reclining. Why should I be punished for a rude passenger in front of me who decides to punish me by reclining their seat?"

Pros: "Plane and staff was comfortable"
Cons: "Weather delays resulted in me being rebooked on a flight nearly 6 hours later, even though there was a connection within 2 hours"

Pros: "The flight attendant was nice."

Cons: "I didn’t appreciate that your rude flight attendant allowed another passenger to move suitcase and she got an attitude with me. Delta there is always something on your flights."

Pros: "very friendly crew"

Cons: "My luggage was sent to another city"

Pros: "Overall everything was great would definitely recommend delta to others ."

Pros: "Air crew was excellent"

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: "The flight is short"
Cons: "Delayed from 930pm to 6am. Didn't tell us till almost midnight. Because of scheduling issues not weather or anything. The check in people had no idea what I was talking about when I tried to check in for my 6am rescheduled flight."

Pros: "The entertainment"
Cons: "Had to pay for bags"

Pros: "Not much to like."
Cons: "our connecting flight was delayed 12 hours. The person who checked us in for the flight to Idaho falls checked our baggage for our return flight home, which was an entire week later. So our baggage got sent back to our starting destination and not Idaho falls"

Cons: "The line for printing the pass was not open. I showed up 2 hrs prior. After dealing with the kiosk for more than 1/2 hour. I missed my flight."

Pros: "Crew was good"
Cons: "Flight was delayed 4 plus hours. Found out about delay from email update vice crew at airport."

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: "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: "It's Delta so I got miles"
Cons: "Cramped seats, no food. It's not what you'd expect from Delta. Exit row doesn't help, and forget the bulkhead if you're over 5ft 8in. Look for a flight with first class or a bigger plane, they have them"

Pros: "-forgot to charge me for wine"
Cons: "-chair was broken -tray was broken -had to spend $33 for wifi that didn't even work -didn't have everything they say they offer to guests on the flight"

Pros: "Smooth flight."
Cons: "I have broad shoulders and there was a larger gentleman on the window seat. Being in the middle seat made for a very very cramped flight the whole way. Lots of skin to skin arm contact for much of the flight. There was no way to avoid it."

Pros: "The crew was nice and helpful."
Cons: "The economy plus wasn't nearly as nice as any other airlines. It gave the least amount of extra leg room and the only other amenity they gave was a toothbrush. Even United economy plus is bigger. Plus if you want to change anything you have to pay include just to try and go stand by on an earlier flight."

Pros: "The short flight was fine. Crew was friendly."
Cons: "Because we arrived to LAX from SAN so late we had to run to the next gate and barely made the flight. The overhead bins were already very full so we had to stuff our stuff at our feet. Since we arrived so late it would have been better if they had allowed those with a tight connection to disembark first."

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."

Cons: "small aisles and space in the seats. me and my wife were seated"

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: "The flight actually took off."
Cons: "No forewarning of weather impacting flights 3 days later, allowing passengers to potentially change flights. Two hour delay became a four delay which became a five hour delay. Delta reps entirely unhelpful when I asked if anything could be done, "Atlanta is a disaster right now." I get that these things happen from time to time, but Delta is handling this very poorly. I'm actually waiting for my flight out of Atlanta and it's also been delayed, luckily only for 30 minute this time."

Pros: "We flew 1st class and this was out first time on a 767. Wow! Amazing seats that recline as well as foot rests that extend. USB and electrical outlets, bigger tray tables, massaging seats, etc. I had a special meal request and the flight attendant was very professional and pleasant about it."
Cons: "Nothing. It was great!"

Cons: "The handle on my checked bag was broken when I got it at immigration. Not sure why they pulled out the handle since it was retracted when checked in."

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: "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 Aruba to Chicago Midway Airport

Airlines flying from Aruba 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 Aruba to Chicago Midway Airport

Mandatory masks

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

Social distancing seating

Middle seats unavailable to book on flights from Aruba to Chicago Midway Airport

Pre-flight testing

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

Book cheap flights from Aruba to Chicago Midway Airport

Recent round-trip flight deals

5/4
Wed
1 stop
Delta
9h 06m
AUA - MDW
5/9
Mon
1 stop
Delta
7h 10m
MDW - AUA
5/4
Wed
2 stops
Delta
19h 14m
AUA - MDW
5/9
Mon
1 stop
Delta
7h 10m
MDW - AUA
5/8
Sun
1 stop
Delta
9h 06m
AUA - MDW
5/12
Thu
1 stop
Delta
7h 10m
MDW - AUA
5/8
Sun
1 stop
Delta
9h 06m
AUA - MDW
5/12
Thu
2 stops
Delta
18h 15m
MDW - AUA

Recent one-way flight deals

12/27
Mon
1 stop
Delta
9h 42m
AUA - MDW
12/28
Tue
2 stops
Delta
20h 48m
AUA - MDW
12/29
Wed
2 stops
Delta
42h 38m
AUA - MDW
12/25
Sat
2 stops
Delta
21h 28m
AUA - MDW
12/26
Sun
2 stops
Delta
20h 48m
AUA - MDW
12/31
Fri
1 stop
Delta
20h 52m
AUA - MDW
1/31
Mon
2 stops
Delta
18h 43m
AUA - MDW
12/31
Fri
2 stops
Delta
42h 38m
AUA - MDW
12/26
Sun
1 stop
Delta
19h 12m
AUA - MDW
12/19
Sun
1 stop
Delta
19h 12m
AUA - MDW
12/19
Sun
2 stops
Delta
18h 38m
AUA - MDW
2/7
Mon
1 stop
Delta
7h 55m
AUA - MDW
2/7
Mon
3 stops
Multiple Airlines
21h 58m
AUA - MDW
2/6
Sun
3 stops
Multiple Airlines
36h 06m
AUA - MDW
12/25
Sat
3 stops
Multiple Airlines
23h 15m
AUA - MDW
1/8
Sat
1 stop
Delta
7h 55m
AUA - MDW
2/13
Sun
2 stops
Delta
19h 25m
AUA - MDW
4/9
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Multiple Airlines
25h 37m
AUA - MDW
4/9
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3 stops
Multiple Airlines
25h 37m
AUA - MDW
4/2
Sat
3 stops
Multiple Airlines
25h 37m
AUA - MDW
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