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Find cheap flights from Chicago Midway Airport to Massachusetts from $64

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 8/21. 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
Tue 7/2
Tue 7/9

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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$688
Albany
Albany1 stop$256

Good to know

Low season

February

High season

May

Cheapest flight

$64
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 70% lower on average.
Flight from Chicago Midway Airport to Boston

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 14% 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 10402 reviews
7.4Food
7.9Comfort
8.2Boarding
8.0Entertainment
8.6Crew
Airline reviews

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

10.0 ExcellentBarb, Jun 2024MSP - JFK
Read more about Delta reviews

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

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!

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

The boarding process was terrible especially with an indirect flight Chicago to Seattle to San Diego was terrible talking about we overbooked a flight idk if I’d take this airline ever again we got off our flight from Chicago to Seattle and we traveled for business and they told us our connecting flight was over booked and their was no seats asking people to take a delayed next flight and they don’t tell anyone coughing to wear masks seats 30A-B were terrible during the flight no one wants to sit next to people coughing all around I don’t want to be sick traveling for work or get sick anytime it’s very upsetting the staff doesn’t take this stuff serious to tell them to wear masks when they see people coughing and sneezing

The plane was not on time for boarding or departure or arrivals.

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

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

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.

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
8/14Wed
1 stopFrontier
10h 26mMDW-BOS
8/20Tue
1 stopFrontier
7h 37mBOS-MDW
$126
8/20Tue
1 stopFrontier
10h 26mMDW-BOS
8/28Wed
1 stopFrontier
13h 39mBOS-MDW
$134
8/10Sat
1 stopDelta
4h 41mMDW-ALB
8/15Thu
1 stopDelta
3h 38mALB-MDW
$256
7/3Wed
1 stopDelta
4h 37mMDW-ALB
7/6Sat
1 stopDelta
3h 49mALB-MDW
$271
6/14Fri
1 stopAllegiant Air
10h 15mMDW-BOS
6/16Sun
2 stopsAllegiant Air
25h 00mBOS-MDW
$317
6/14Fri
1 stop
10h 15mMDW-BOS
6/16Sun
3 stops
22h 22mBOS-MDW
$351
6/27Thu
nonstopSouthwest
2h 15mMDW-BOS
7/7Sun
nonstopSouthwest
2h 45mBOS-MDW
$381
6/14Fri
3 stops
23h 46mMDW-BOS
6/16Sun
2 stops
25h 00mBOS-MDW
$383
6/27Thu
1 stopSouthwest
5h 05mMDW-BOS
7/7Sun
nonstopSouthwest
2h 45mBOS-MDW
$414

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Recent one-way flight deals

8/21Wed
1 stopFrontier
10h 26mMDW-BOS
$64
6/11Tue
1 stopFrontier
7h 42mMDW-BOS
$68
6/11Tue
1 stopFrontier
7h 42mMDW-BOS
$69
6/21Fri
1 stopAllegiant Air
10h 15mMDW-BOS
$108
7/1Mon
1 stopAllegiant Air
10h 15mMDW-BOS
$128
6/24Mon
2 stops
16h 17mMDW-BOS
$137
7/24Wed
1 stopDelta
5h 58mMDW-BDL
$138
8/18Sun
nonstopSouthwest
2h 15mMDW-BOS
$142
7/29Mon
1 stopDelta
4h 43mMDW-ALB
$148
6/14Fri
2 stops
16h 17mMDW-BOS
$148

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Last minute flights from Midway to Massachusetts

Last minute flight, train and bus deals

6/6Thu
multi-stopFrontier
10h 25mMDW-BOS
6/11Tue
multi-stopFrontier
9h 44mBOS-MDW
$148
6/6Thu
multi-stopFrontier
10h 25mMDW-BOS
6/12Wed
multi-stopFrontier
14h 40mBOS-MDW
$149
6/5Wed
multi-stopDelta
6h 31mMDW-BOS
6/12Wed
multi-stopDelta
4h 28mBOS-MDW
$334
6/4Tue
multi-stopDelta
7h 13mMDW-BOS
6/6Thu
multi-stopDelta
4h 31mBOS-MDW
$356
6/4Tue
nonstopSouthwest
2h 15mMDW-BOS
6/5Wed
nonstopSouthwest
2h 35mBOS-MDW
$368
6/4Tue
multi-stopSouthwest
8h 00mMDW-BOS
6/5Wed
nonstopSouthwest
2h 40mBOS-MDW
$378
6/6Thu
multi-stop
7h 02mMDW-BOS
6/13Thu
multi-stop
25h 00mBOS-MDW
$896
6/6Thu
multi-stop
9h 05mMDW-BOS
6/13Thu
multi-stop
25h 00mBOS-MDW
$902
6/6Thu
multi-stopPorter Airlines
9h 05mMDW-BOS
6/17Mon
multi-stopPorter Airlines
10h 07mBOS-MDW
$928
6/6Thu
multi-stopPorter Airlines
9h 05mMDW-BOS
6/12Wed
multi-stopPorter Airlines
10h 07mBOS-MDW
$973

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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