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Find cheap flights from Chicago Midway Airport to Massachusetts from $62

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Massachusetts departing on 6/13. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sat 6/29
Sat 7/6

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Best Massachusetts Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Boston
Boston1 stop$116
Nantucket
Nantucket2 stops$923
Albany
Albany1 stop$256

Good to know

Low season

February

High season

May

Cheapest flight

$62
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 71% lower on average.
Flight from Chicago Midway Airport to Hartford

FAQs - booking Massachusetts flights

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

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Massachusetts.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Massachusetts from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

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

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Massachusetts with an airline and back to Chicago Midway Airport with another airline.

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

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Massachusetts from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Massachusetts

  • Morning departure is around 38% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 3 airlines serving from Midway to Massachusetts

 
Need help choosing which airline to fly with from Midway to Massachusetts? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10457 reviews
7.9Comfort
8.0Entertainment
7.4Food
8.2Boarding
8.6Crew
Airline reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

10.0 ExcellentMichael, May 2024SJC - ATL
Read more about Delta reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The boarding was horrible. You couldn’t hear the announcements at all. Probably because there is so much in the area for businesses. They need a louder PA system. Other than that it was a good Delta experience.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

Terrible. Delta delays caused us to miss our flight and they did nothing to fix it.

The A330-200 was showing its age but otherwise this was a pleasant flight with friendly crew. The meals/snack provided were pretty good.

The most unprofessional and disorganized experience I’ve ever had with an airlines. After the flight was diverted on the runway and we returned to the gate, there was no communication about the plans and it took an additional 5 hours to get set up with a hotel and a new flight, information that was not readily given to the passengers and mostly gotten second hand from what other passengers heard from each other. Based on this experience I cannot recommend flying delta again

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

My flight was cancelled!!! I had to spend 200.00 on another flight!!

Worst airline experience ever. Lost my IPad going thru security. Charged for my dog carriage at the gate not at ticket counter. Gave away my seat 6D. Expressed I wanted my seat back after charging me 99 for dog carriage. Should have thrown it out. Had a 16 yr old Yorkie heading to Boston after being a snowbird. Seats small. Very bad experience. Still don’t have my IPad. Horrible

Flight delayed then canceled! I will NEVER fly Spirit Airlines again and will tell all my friends!

Delayed..4 times...completely disorganized boarding. After 5 hours they scrambled to move ppl off plane bc they overbooked. Then they didn't have a cabin crew. WiFi on plane didn't work. Zero amenities. Once we boarded we sat on tarmac for an hour. Explore all alternate options including purchasing a pair of hiking boots and walking to your destination instead of flying spirit.

The seat was very uncomfortable from Boston to Nashville. Otherwise the flight was excellent.

I had a phobia for Spirit and now is 100% confirmed. Flight delayed, missed connecting flight and staying overnight . Now not even able to get my boarding pass until I’ll get into the airport. It’s really really bad at this point

the landing was terrible. the plane touched down and had take off. the plane flew around and landed a second time.i understand the weather might of been the problem. It was a scary experience and no explanation from the captain.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

My experience with frontier staff at the Denver airport was absolutely horrible. The manager on duty was even worst if was the worst experience I have ever had, I have never been treated so poorly as a customer in my life! The staff was extremely rude, eye rolls and attitude and then refusal to help me at all. I wish I could never fly frontier again that’s how horrible it was!

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Plane could have been more on time. More leg room .

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

Book cheap flights from Chicago to Massachusetts

Recent round-trip flight deals

8/31Sat
1 stopFrontier
10h 26mMDW-BOS
9/3Tue
1 stopFrontier
7h 37mBOS-MDW
$116
6/11Tue
1 stopFrontier
7h 42mMDW-BOS
6/12Wed
1 stopFrontier
25h 15mBOS-MDW
$120
6/11Tue
nonstopSouthwest
2h 15mMDW-BOS
6/14Fri
nonstopSouthwest
2h 35mBOS-MDW
$246
6/11Tue
1 stopSouthwest
11h 45mMDW-BOS
6/14Fri
nonstopSouthwest
2h 35mBOS-MDW
$255
8/7Wed
1 stopDelta
4h 41mMDW-ALB
8/14Wed
1 stopDelta
3h 38mALB-MDW
$256
7/3Wed
1 stopDelta
4h 45mMDW-BDL
7/10Wed
1 stopDelta
4h 01mBDL-MDW
$276
6/20Thu
1 stopAllegiant Air
7h 09mMDW-ALB
6/23Sun
2 stopsAllegiant Air
24h 35mALB-MDW
$416
6/25Tue
1 stop
9h 12mMDW-BOS
7/1Mon
3 stops
15h 18mBOS-MDW
$493
6/25Tue
2 stops
9h 05mMDW-BOS
7/1Mon
3 stops
15h 18mBOS-MDW
$499
6/27Thu
1 stopAllegiant Air
7h 09mMDW-ALB
6/30Sun
2 stopsAllegiant Air
24h 35mALB-MDW
$516

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Recent one-way flight deals

6/13Thu
1 stopFrontier
6h 44mMDW-BDL
$62
8/21Wed
1 stopFrontier
10h 26mMDW-BOS
$64
6/13Thu
nonstopSouthwest
2h 15mMDW-BOS
$114
7/3Wed
1 stopDelta
4h 37mMDW-ALB
$117
6/21Fri
1 stopAllegiant Air
10h 15mMDW-BOS
$118
6/21Fri
1 stopAllegiant Air
10h 15mMDW-BOS
$123
7/9Tue
1 stopDelta
4h 41mMDW-ALB
$124
6/14Fri
2 stopsSouthwest
10h 15mMDW-BOS
$128
8/12Mon
2 stops
20h 58mMDW-BOS
$149
6/14Fri
2 stops
16h 17mMDW-BOS
$151

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Last minute flights from Midway to Massachusetts

Last minute flight, train and bus deals

6/3Mon
multi-stopFrontier
8h 27mMDW-BOS
6/5Wed
multi-stopFrontier
6h 43mBOS-MDW
$227
6/2Sun
multi-stopFrontier
10h 17mMDW-BDL
6/5Wed
multi-stopFrontier
14h 52mBDL-MDW
$232
6/3Mon
multi-stopFrontier
8h 27mMDW-BOS
6/7Fri
multi-stopFrontier
14h 29mBOS-MDW
$252
6/3Mon
nonstopSouthwest
2h 15mMDW-BOS
6/6Thu
nonstopSouthwest
2h 35mBOS-MDW
$276
6/3Mon
multi-stopSouthwest
11h 15mMDW-BOS
6/6Thu
nonstopSouthwest
2h 35mBOS-MDW
$286
6/4Tue
multi-stopDelta
5h 51mMDW-BOS
6/5Wed
multi-stopDelta
4h 31mBOS-MDW
$314
6/4Tue
multi-stopDelta
7h 13mMDW-BOS
6/16Sun
multi-stopDelta
4h 28mBOS-MDW
$334
5/31Fri
multi-stop
19h 55mMDW-BOS
6/2Sun
multi-stop
21h 44mBOS-MDW
$565
5/31Fri
multi-stop
19h 55mMDW-BOS
6/2Sun
multi-stop
21h 41mBOS-MDW
$616
6/4Tue
multi-stopPorter Airlines
14h 42mMDW-BOS
6/5Wed
multi-stopPorter Airlines
19h 12mBOS-MDW
$948

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Chicago Midway Airport - Massachusetts Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Massachusetts - Chicago Midway Airport

Cabin classes:

$369