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Find cheap flights from Chicago Midway Airport to Massachusetts from $56

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 6/11. 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
Thu 6/6
Thu 6/13

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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$99
Albany
Albany1 stop$263

Good to know

Low season

February

High season

October

Cheapest flight

$56
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 53% increase in price.
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 21% cheaper 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 10810 reviews
8.6Crew
7.4Food
7.9Comfort
8.0Entertainment
8.2Boarding
Airline reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

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

I was traveling with my 85 years old grandma and 60 years old mother. Which I requested to get a wheelchair. I went to the Delta Kiosk and asked for a wheelchair.  They brought a wheelchair and 2 minutes (without exaggerating, time is important for me as I am well disciplined with a military background) later they said that the wheelchair belongs to American Airlines, so we need to switch it.  We were like where is the other one so my grandma can use it? They are like, "it's on its way, she has to wait for the other one" I asked them why does she have to wait? Is it ok for her to sit on this one when the other one arrives. Answer was "NO". I guess lack of common sense was the issue. I started to explain to the agent that she can not stand still or wait. Finally, someone said that in spanish "she can not stand, let's wait for the other one" . Delta's wheelchair came, without an attendant or helper. They brought that wheelchair and left it in the middle of the airport. Nobody seemed to care. I had to push her to the gate. Then they finally realized that "wait a minute, there is something wrong with that". So they send someone, who later started harassing us, to tell us how he works for cash tips. Then a "Private Security Interviewer" approached us. I think his name was Carlos (His descriptions - tall for an average worker, ginger curly hair, wears glasses, overweight). He did not represent himself. All he did was show his badge for two seconds and when (later on) I asked him what his name was, he said "I already told you at the beginning". At that point we were waiting to be called at the Delta Kiosk (this is prior to the Customs first check in point). So, Delta Airlines hired "Private security interviewers" to make sure that nobody brings anything illegally to the US. Which is great, makes me feel safe and secure. But, it does not serve the purpose. Let me explain to you why. These interviewers do not know what they are doing or saying and you can clearly see that. They think that they are CBP or Immigration officers. They will get angry If you ask them any questions. Then they will put all these stickers on the back of your passport like they caught "Pablo Escobar". At one point I was sarcastic and told the interviewer that "I like those stickers, It's my hobby and I am collecting them. Can I have more of those?"  and interviewers eyes and brain goes like "error 404". He did not know how to react or respond to that. Then he flags my itinerary on his iPad. Trying to give me a hard time since I asked him about his name, so I can call him by his name. But of course that did not change the fact that his lack of english made everything even harder. After 45 mins of wait and clearing the "Private Security Interviewer" you would think that we are going to be all set to depart. I was wrong. We waited in line to go through the security line, just like other citizens. No wheelchair, disability, seniority etc were important for her. They treat us like she is in her twenties.  On several occasions they forced her to stand up. She was like "I swear to God that I can not walk, my son I wish I could walk, but I can not". They did not seem like they cared. Then finally they realized that she is legit disabled. They let her pass on a wheelchair. At the gate, Carlos showed up to make sure that I am going through the secondary check. They pulled me to the secondary check. And started asking me about my luggage. My response was "I only have one carry-on bag, to make everyone's (including my life) life easier". They asked the same question over again "Sir, do you just have only one bag?" I replied saying "Yes". She did not believe me and said "Just only one". So, I thought she did not believe me and I said "Yes, Si, Si, solo uno". She looked at me and then turned to the agent (Carlos) and stared at him like "did you not ask him about his bags, did you not know that he only had one carry on?". I am sorry to say that but they just looked like a bunch of idiots who do not know what they are doing. Finally they released me after a minute of secondary check. Meanwhile everyone is boarding and my grandma is waiting on her wheelchair. Then we approached the gate agent and I asked her if I could sit next to my family, if they had any seats available. She replied that "I can not change any seat at the gate, I do not have any authority". I replied "I understood". We got on the plane last and I asked our flight attendant if I could change my seat to be next to my family. FYI, their seats were 10 B and C, mine was the 35 D. Meanwhile there were empty seats on 10 D and F. Even flight attendants surprisingly said that "why did she put you all the way back, while we had 1/2 full flight. I will go and ask her". Our flight attendant was great and he made sure that I am next to my family. He went above and beyond and he gave the closest seat to the. Flight was good. Delta Airlines failed to bring the wheelchair when we arrived. Excuse was "Gate changed, that is why". I walked outside and grabbed an empty wheelchair. I put my grandma and brought her to the Customs. Then a Delta Airline worker approaches me and says that you can not move this wheelchair, it belongs to the gate. We will bring you a new one. A CBP officer heard our conversation and jumped in and said, "wait a minute you want her (pointed my grandma) to wait here while you bring her wheelchair?". He (delta worker) responded "yes sir". But when he talks to me, no sir, nothing. The CBP officer goes "Nope, she is not waiting here and I will make sure to pull her wheelchair". If that officer was not there we probably would have had to wait and be forced to change the wheelchair. The CBP officer, again the CBP officer, not the Delta employee, pushed our wheelchairs to the gate. Sincerely,

The boarding agents appeared to do the minimum customer service. They did not appear to try to find solutions to problems.

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…

Service was awesome 👍🙏 thank you Spirit Airlines...love the Big Seat...😎

Crew was very engaging and welcoming. Seat very uncomfortable and inadequate leg room made the trip a long 3 hours.

Plane two hours late. Missed flight to Boston. Spirit should have already reticketed us at the last jet blue flight. But no. No help, only confusion. Reticketing line a mile long. Agent couldn’t care less whether I lived or died. Offered flight two days later - unacceptable. Now going - hopefully - via Orlando to Boston with a 7 hour layover. Locator GJLSJG BTW, am a travel counselor at a large corporate agency.

The flight was delayed. The boarding process disorganized. Poor communication regarding the delays. We were sitting on the runway in Boston for over 1-hr. Again very poor communication regarding the status. Bags didn’t arrive after almost 2-hr wait. I gave up and went home without my bag and had to return to the airport to pick it up the next day. Very exhausting experience!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

Book cheap flights from Chicago to Massachusetts

Recent round-trip flight deals

5/18Sat
1 stopFrontier
11h 35mMDW-BOS
5/22Wed
1 stopFrontier
11h 39mBOS-MDW
$99
5/29Wed
1 stopFrontier
23h 51mMDW-BOS
6/5Wed
1 stopFrontier
6h 43mBOS-MDW
$108
5/29Wed
1 stopFrontier
23h 51mMDW-BOS
6/8Sat
1 stopFrontier
24h 19mBOS-MDW
$110
5/17Fri
1 stopFrontier
21h 35mMDW-BOS
5/22Wed
1 stopFrontier
6h 50mBOS-MDW
$111
5/19Sun
1 stopFrontier
24h 15mMDW-BOS
5/22Wed
1 stopFrontier
6h 50mBOS-MDW
$112
5/17Fri
2 stopsFrontier
20h 24mMDW-BOS
5/22Wed
1 stopFrontier
6h 50mBOS-MDW
$116
5/17Fri
nonstopSouthwest
2h 15mMDW-BOS
5/20Mon
nonstopSouthwest
2h 40mBOS-MDW
$195
6/5Wed
2 stopsDelta
8h 47mMDW-ACK
6/12Wed
2 stopsDelta
7h 24mACK-MDW
$288
8/14Wed
2 stopsDelta
19h 15mMDW-BOS
8/19Mon
2 stopsDelta
20h 29mBOS-MDW
$305
8/14Wed
2 stopsDelta
19h 15mMDW-BOS
8/22Thu
1 stopDelta
7h 42mBOS-MDW
$310

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Recent one-way flight deals

6/11Tue
1 stopFrontier
7h 42mMDW-BOS
$56
8/20Tue
1 stopFrontier
10h 26mMDW-BOS
$57
6/28Fri
1 stopAllegiant Air
10h 15mMDW-BOS
$125
5/13Mon
2 stops
17h 19mMDW-BOS
$151
6/14Fri
2 stops
20h 40mMDW-BOS
$154
6/4Tue
1 stopDelta
7h 13mMDW-BOS
$158
6/7Fri
1 stopDelta
5h 42mMDW-BOS
$159
7/1Mon
1 stopAllegiant Air
10h 15mMDW-BOS
$166
6/10Mon
2 stopsPorter Airlines
9h 05mMDW-BOS
$258
6/10Mon
2 stopsPorter Airlines
9h 05mMDW-BOS
$260

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Last minute flights from Midway to Massachusetts

Last minute flight, train and bus deals

5/11Sat
multi-stopFrontier
10h 51mMDW-BOS
5/15Wed
multi-stopFrontier
11h 44mBOS-MDW
$209
5/11Sat
multi-stopFrontier
10h 51mMDW-BOS
5/15Wed
multi-stopFrontier
11h 44mBOS-MDW
$211
5/11Sat
multi-stopFrontier
10h 51mMDW-BOS
5/13Mon
multi-stopFrontier
11h 49mBOS-MDW
$212
5/11Sat
multi-stopFrontier
10h 51mMDW-BOS
5/13Mon
multi-stopFrontier
11h 49mBOS-MDW
$217
5/11Sat
multi-stopDelta
4h 42mMDW-BOS
5/14Tue
multi-stopDelta
5h 04mBOS-MDW
$353
5/8Wed
multi-stopDelta
7h 13mMDW-BOS
5/15Wed
multi-stopDelta
5h 04mBOS-MDW
$357
5/12Sun
multi-stop
13h 22mMDW-BOS
5/16Thu
multi-stop
28h 14mBOS-MDW
$396
5/10Fri
multi-stop
17h 19mMDW-BOS
5/16Thu
multi-stop
28h 14mBOS-MDW
$564
5/12Sun
multi-stopPorter Airlines
14h 42mMDW-BOS
5/13Mon
multi-stopPorter Airlines
19h 12mBOS-MDW
$966
5/12Sun
multi-stopPorter Airlines
8h 50mMDW-BOS
5/15Wed
multi-stopPorter Airlines
9h 02mBOS-MDW
$993

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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