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Find cheap flights from Chicago Midway Airport to Massachusetts from $90

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 7/31. 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 6/22
Sat 6/29

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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$156
Albany
Albany1 stop$302

Good to know

Low season

February

High season

May

Cheapest flight

$90
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 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 18% 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 10561 reviews
7.4Food
8.2Boarding
7.9Comfort
8.0Entertainment
8.6Crew
Airline reviews

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

6.0 GoodPeter, May 2024SLC - HNL
Read more about Delta reviews

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

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

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

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.

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.

The flight attendants were very personable, extremely friendly, and had a very good feeling of the energy around them not to mention they’re very funny and engaging. What made up for the discomfort of the seats and the fact that the plane sat for a long time on the Turmac. Not sure if the pilot was new, but the landing was very rough sort of like I was at a magic mountain theme park ride that was built in 1959

Flight was delayed 2+ hours missed a concert because of it…

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 :-(

Check in online was easy. Seats aren’t very comfortable

Fecal matter in seat back pocket. Presumably from a kids diaper.

Worst airline to travel with. They treat you like a prisoner in a jailhouse barking out orders and threats. Nickle and dime you to the same price or higher than a respectable airline like one of the big 3 . Might as well fly with standard airlines

Well I mean u get what u pay for so 🤷‍♂️

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

Book cheap flights from Chicago to Massachusetts

Recent round-trip flight deals

5/30Thu
1 stopFrontier
24h 15mMDW-BOS
6/1Sat
1 stopFrontier
7h 58mBOS-MDW
$156
7/2Tue
1 stopFrontier
7h 42mMDW-BOS
7/9Tue
1 stopFrontier
11h 27mBOS-MDW
$159
6/9Sun
nonstopSouthwest
2h 15mMDW-BOS
6/12Wed
nonstopSouthwest
2h 35mBOS-MDW
$216
6/9Sun
nonstopSouthwest
2h 15mMDW-BOS
6/12Wed
1 stopSouthwest
8h 40mBOS-MDW
$236
8/17Sat
1 stopDelta
4h 36mMDW-BDL
11/20Wed
1 stopDelta
3h 56mBDL-MDW
$291
7/3Wed
1 stopDelta
4h 37mMDW-ALB
7/6Sat
1 stopDelta
3h 49mALB-MDW
$302
6/7Fri
2 stops
20h 08mMDW-BOS
6/9Sun
2 stops
24h 48mBOS-MDW
$395
6/21Fri
1 stop
10h 15mMDW-BOS
6/23Sun
3 stops
25h 18mBOS-MDW
$397
6/21Fri
1 stopAllegiant Air
10h 15mMDW-BOS
6/23Sun
2 stopsAllegiant Air
25h 00mBOS-MDW
$414
6/20Thu
1 stopAllegiant Air
7h 09mMDW-ALB
6/23Sun
2 stopsAllegiant Air
24h 35mALB-MDW
$428

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Recent one-way flight deals

7/31Wed
1 stopFrontier
8h 58mMDW-BOS
$90
7/2Tue
1 stopFrontier
7h 42mMDW-BOS
$91
6/21Fri
1 stopAllegiant Air
10h 15mMDW-BOS
$108
6/21Fri
1 stopAllegiant Air
10h 15mMDW-BOS
$116
8/12Mon
1 stopDelta
4h 07mMDW-ALB
$138
7/31Wed
1 stopDelta
5h 31mMDW-BDL
$138
6/14Fri
2 stops
16h 17mMDW-BOS
$150
6/14Fri
2 stops
16h 17mMDW-BOS
$152
6/10Mon
1 stopPorter Airlines
6h 07mMDW-BOS
$249
7/14Sun
2 stopsPorter Airlines
8h 50mMDW-BOS
$254

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Last minute flights from Midway to Massachusetts

Last minute flight, train and bus deals

5/27Mon
multi-stopFrontier
23h 36mMDW-BDL
5/29Wed
multi-stopFrontier
6h 26mBDL-MDW
$273
5/25Sat
multi-stopFrontier
23h 01mMDW-BDL
6/4Tue
multi-stopFrontier
6h 46mBDL-MDW
$281
5/28Tue
multi-stopSouthwest
7h 10mMDW-BOS
5/30Thu
nonstopSouthwest
2h 40mBOS-MDW
$296
5/28Tue
multi-stopSouthwest
7h 10mMDW-BOS
5/30Thu
nonstopSouthwest
2h 40mBOS-MDW
$300
5/25Sat
multi-stopDelta
5h 39mMDW-BOS
5/27Mon
multi-stopDelta
4h 31mBOS-MDW
$356
5/24Fri
multi-stopDelta
5h 17mMDW-BOS
5/27Mon
multi-stopDelta
7h 07mBOS-MDW
$376
5/28Tue
multi-stopPorter Airlines
6h 07mMDW-BOS
5/31Fri
multi-stopPorter Airlines
12h 52mBOS-MDW
$824
5/26Sun
multi-stopPorter Airlines
8h 50mMDW-BOS
6/29Sat
multi-stopPorter Airlines
7h 37mBOS-MDW
$843
5/26Sun
multi-stop
8h 50mMDW-BOS
6/29Sat
multi-stop
9h 21mBOS-MDW
$896
5/27Mon
multi-stop
22h 55mMDW-BOS
6/9Sun
multi-stop
20h 59mBOS-MDW
$957

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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