Find cheap flights from Iowa to Chicago Midway Airport

MDW

Find cheap flights from Iowa to Chicago Midway Airport

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Boston (BOS)
Chicago Midway
Fri 10/30
Fri 11/6
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Good to know

Low season

August Best time to beat the crowds with an average 5% drop in price.

High season

April Most popular time to fly with an average 18% increase in price.

Average price of a round-trip

$297 (avg. price over the last 2 weeks)

Good deal for a round-trip

$159 or less

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Top airlines flying Iowa to Chicago Midway

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 28,720 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Pros: "Everything except the delay was fine, not extraordinary."
Cons: "7-hour flight delay. If this was a European flight we would have been entitled to at least $250 for our inconvenience. We were not offered anything to compensate us for a 7hour delay, which was ridiculous."

Cons: "Needed assistance for limited mobility to make connections at ATL was not provided. Caused us to miss connections and had two falls trying to get around. Air France was terrible. Very limited food and beverage service left us hungry and thirsty on 7 to 10 hour flights."

Pros: "Fast service and precise timing"

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: "The plane was nice, entertainment options were great, pilot was super kind."

Pros: "The check in process was smooth and the flight crew were pleasant"
Cons: "some of the TSA crew were rude/seemed to be doing a lazy job with helping load items on the belt"

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

Pros: "Yes Crew was amazing. Seat was comfortable"
Cons: "No comment"

Cons: "It was just the weather. I don't handle turbulence well. Delta crew was amazing as always."

Pros: "On time arrival is always appreciated."
Cons: "Overhead compartment jammed with someone else's carry on. We paid for "comfort seating" and I frankly didn't see any difference - if there was more room on those seats, it was small enough I couldn't SEE it."

Pros: "Was ultimately seated in Comfort+ even though I had an Economy ticket."
Cons: "Seat assignment with Economy ticket. More than willing to be asked to move for family seating, etc. Just feels nicer knowing you have an actual seat."

Pros: "Bags were waiting on Carousel"
Cons: "Slightly delayed due to incoming flight delayed"

Cons: "No wifi"

Pros: "Crew was very friendly. Food was excellent"

Pros: "Accurate arrival time"

Cons: "Crazy rough, fast landing but not boring!!!"

Pros: "The food and the treatment"

Pros: "see above"

Cons: "The Delta staff in the Augusta airport seemed to have a hard time with getting people boarded - the instructions for what zone was being boarded and who could take what baggage or who was going to need to gate check bags was... not good."

Pros: "Although our flight was fully booked. The crewmembers on this flight was professional, friendly and efficient. We boarded quickly and took off on time. We even arrived ahead of schedule. Each passenger was given free headphones and complimentary beverages and snacks. I love Delta they are a cut above the rest. They are constantly striving to put the customers needs and wants top priority"
Cons: "Tight seats need more legroom"

Cons: "The baggage drop attendant was very unhelpful when I asked if she could help me sort out an issue (when I checked in online for the second leg of my trip, i paid for my bag then but they wanted me to pay again for my first flight) and just dismissed me and said she couldn't help, making me pay again for my bag. First time I've ever had an unpleasant experience with Delta."

Pros: "They waited for me as I was late"
Cons: "My suitcase was damage"

Pros: "Zones are more delineated."
Cons: "People were obviously cutting in line and edging up before their zones were called."

Pros: "Crew and boarding were great, which I expect from a premium carrier like delta."
Cons: "Perfect day outside, not a busy day or time to fly. The email forbhe plane being late was was too last minute. A heads up sooner would have been nice. That way we’re not waiting at the airport."

Pros: "Comfortable seats, friendly staff."
Cons: "The wifi was not working during this flight. The ceiling light/fan controls are too close to the window for the aisle seat to reach them. During boarding, it was too hot. The boarding process was delayed 10-15 minutes without any updates."

Pros: "Truly, everyone of the flight attendants were delightful, professional and caring."
Cons: "Food. I didn’t remember to bring food this time but thankfully I was far enough forward there was some. Thanks"

Cons: "Flight delayed 2 hrs"

Pros: "We were in the plane for 3 hours before we could depart. No one offered us a drink or snack."

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: "Flight was on time. Boarded quickly with no fuss."

Cons: "Older plane and seemingly frustrated crew. They had very little patience."

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: "Fligth were on time"
Cons: "My flight from Montreal to Atlanta was 2:30 min Left at 6:10 arrive at 8:30 roughly Tried twice to get to my connection earlier and get 9:30 instead of 12:09 fligth to Daytona Delta was not flexible to allow me to book saying i did not have 55 min in between fligth which i had than lear n it will cost $75.00 to change the fligth - What? Very disappointed of Delta - lost 3 hrs at the airport today"

Pros: "Same as above."

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

Pros: "Super quick"

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: "Service and staff"

Pros: "Everything was pretty good like usual, except when we landed we sat on the runway for 45 minutes waiting for a gate as ours was occupied by a plane that was having mechanical issues. Not great."

Pros: "Business as usual and we actually arrived abit earlier than projected. Cudos to the pilot and crew."

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: "Good heads up to turbulence."

Pros: "Smooth"
Cons: "Delayed because the airline misschdduled the pilots!! We had to wait for pilots to come to the plane... while one the plane"

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

Pros: "As Scheduled, staff hospitality"
Cons: "+$25 extra each bag, seats not near travel companion"

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 boarding process was very well done. Gate agent and flight attendants on top of their game. This is how it is supposed to be done. Thank you."

Pros: "absolutely nothing"
Cons: "no food while waiting flight cancelled and no vendors open in the airport, stood in line for 4 hours only to be told no flights available, wasn't asked if they could feed me, put me up in a hotel, absolutely no compensation for me not being able to see my son graduate in the Air Force."

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: "Give complimentary water"

Pros: "Great crew. Everything was on time. Loved it"

Cons: "Great price. Wonderful flight. Seats are so close knees touched the whole flight."

Cons: "I love the changes that have taken place. I last flew with them 5 years ago and vowed too never fly with them again. Times have changed and they are a great Airline!!!"

Pros: "Easy boarding"
Cons: "A little Snack"

Cons: "Pop and pretzels"

Pros: "the crew was very helpful"
Cons: "seats could have been a little wider"

Cons: "Reclining seats would be great!!"

Cons: "A plan to deal with a hostile mom with a screaming kid that was out of control."

Cons: "Late to load and then put us all on the plane and made us sit on tarmac for over 1 1/2 hours"

Pros: "The plane was clean and crew was very friendly."
Cons: "Delayed departure with no explanation. Other passengers clogged up the overhead bins with small bags, purses and containers of to-go food. Causing me to place my carry on in an overhead bin multiple aisles behind my seat which made for a cluster trying to board and de board."

Pros: "The crew was the best on any flight I have been on. Love their jokes."

Pros: "On time flight... good stew's, all around pleasant experience."
Cons: "the seats are hard and very narrow."

Cons: "Very dissatisfied with boarding and told we had to pay for our luggage but noone else did .I had prepaid for 1 incase I brought big luggage but I brought carry ones. So I was charged 100..but everyone else's was larger"

Pros: "The crew was friendly and the price was low."
Cons: "Communication during our delay."

Pros: "The captain was very good, and we arrived early to our destination. We had to hold back before landing, due to smaller planes landing, so the captain pointed out some areas along our path! Loved it! The flight was smooth."
Cons: "We had to be in the boarding area an hour before the flight was scheduled to leave. However, because of the way that the flights are scheduled, people were still deplaning from the previous flight for 25 minutes after our gate arrival time."

Cons: "I cancelled this flight and somehow it doesn’t show in your records and now I cant find the cancellation.. I am not in Orlando.. last time I will use Kayak."

Pros: "All went well. No real disappointments!"
Cons: "A little cramped but not terrible. Would like to know kayak fee up front before booking and all hidden charges!"

Pros: "Price and direct flights to popular destinations."
Cons: "No frills. Charging $5 for a printed boarding pass seems a bit excessive"

Pros: "People"
Cons: "Extra fees"

Pros: "Going in & out of small airports."
Cons: "We arrived late. Pricing system."

Pros: "The crew was friendly and smiled a lot. Non stop flight from easy and for me, convenient airports. I knew food cost extra so i brought my own."
Cons: "I knew my comfort would be cramped so that was expected. My only complaint was we couldn't understand the boarding instructions at the gate when they were calling zones. The microphone stunk! So because we couldn't understand,, people got in line who shouldn't have yet, and others didn't get in line that should have which seemed to really annoy some mouthy jerk in zone 5....who then had to turn around while boarding bc he forgot his phone, lol. Karma. So, that was my only entertainment and it was pretty great."

Pros: "Availability at last minute was awesome, and the price was excellent. The direct flight was great too!"
Cons: "No frills... no peanuts!"

Cons: "I am so angry booking with them. I booked the flight and then thought, ok I will add a rental car. It said clearly that the rental Car could be canceled up until 24 hours before the flight. Well, 2 weeks before the flight, my friend said, don’t get a rental car, I will have my car. So I cancelled and only then did I find out that once I booked it through their site I could not get a refund for the car and I could only get a voucher for use on one of their flights! And only after they take out any fees and costs that was accrued! So angry!"

Pros: "Quick flight and overall nice crew."
Cons: "None"

Pros: "Keep the free snacks and drinks, NA or soda, I really just miss the legroom (nearly 6’ tall) and cushions, a chair that can ease back a bit. All airlines do this but you are worse than frontier, the major carriers have skimped but not like this."
Cons: "3 hour torture chamber. When she said it was their goal to make us comfortable, but more importantly to keep us safe I snorted laughter. It was a bit better and a lot shorter than the dark passage"

Pros: "Smaller airports make travel easier, and more relaxed. No frills--to get even water on the flight you'll pay for a bottle. Personnel all tend to be friendly and helpful. With Allegiant I've learned to pack lightly and plan travel carefully. It's been worth it as I have been able to see friends and family more often. We even took an impromptu vacation this year when we found a great deal on airfare."

Cons: "Lost my bag"

Pros: "I’m 5’10- tall for a woman but average height I’d say overall. I was so cramped in that seat that next time I will choose another airline to get more rom."
Cons: "No free water?! That’s just cruel considering the flight was over 2 hours."

Pros: "The price was unbeatable, especially if you don't pay for a checked bag, carry-on, or a soda on the flight. Very smooth flight as well."
Cons: "The plane interior looks like it was gutted, then fitted with hard, plastic seats. No headrests, no privacy for the flight attendants. Everything costs extra."

Pros: "The service is not extravagant but completely adequate. Also, it is very consistent every time I fly them."
Cons: "Nothing at all."

Cons: "Left/ arived 30" late"

Cons: "Was assigned a middle seat. I am a small woman and had absolutely no room."

Cons: "Our engine seats at the rear of the plane were of course a little noisy at first. We got these seats on both our flights. Hoped that at least one-way we would have managed seats with a window."

Cons: "No compliment"

Pros: "Both ways were good flights. The return flight however was delayed. We did enjoy buying some tickets from a lady named Valerie in Des Moines who also later had to come on the plane and remove an intoxicated woman. She made everything so easy and simple and enjoyable. And we especially enjoyed the treatment that we received as my husband is a veteran. Thank you so much for that."

Cons: "Both original and 2nd plane had malfunctions which caused extensive delays and doubled boarding time"

Cons: "Did not purchase any food and there was no entertainment offered"

Pros: "Fast flight"
Cons: "Charge for carry on and in flight snacks and drinks (sodas,juices,water)"

Cons: "Two out of three bathrooms out of order"

Cons: "Having to pay for drinks. But, I didn't even not mind it that much. I'd much rather a cheaper flight"

Pros: "Smooth boarding"

Cons: "That you charge for every little thing...surprised you don't charge to use the bathrooms. Don't appreciate having to be your clean up crew either."

Pros: "The price range is far for travelers"
Cons: "They should give free snacks and water juice to the customers that travel with this airline. The other airlines off complimentary snacks and drinks other wise it was a good experience"

Pros: "I sat in the front row so that I had leg room. It was worth the extra 20 bucks."
Cons: "No champagne."

Pros: "Great flight staff and every allegiant like we've had is very friendly and professional"
Cons: "don't like the extra price is tacked on when you purchase your tickets online each suitcase and other fees"

Pros: "The flight attendants were great. Pilots attention to detail..Great."
Cons: "Charging for every little thing including seat choice, bags, snacks. No complimentary beverages or peanuts. Not even water! In the long run, I didn't save money on this trip."

Cons: "The flight was delayed 8 hours"

Pros: "Convenient, Clean, Quality, Care"

Pros: "The crew was very kind. Plane loaded very quickly, every flight we've had on allegiant has left on time! Overall - very good experience!"
Cons: "Seats are TOO small!"

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Iowa to Chicago Midway

Airlines flying from Iowa 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

Mandatory masks

Masks required on board, masks provided

Social distancing seating

Middle seats unavailable to book

Pre-flight testing

Testing for antibodies, testing for symptoms

Book cheap flights from Iowa to Chicago Midway Airport

Recent round-trip flight deals

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