$59 Find Cheap Flights from Chicago Midway Airport to Massachusetts

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 5/9. 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.
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KAYAK searches hundreds of travel sites at once for deals on flights to Massachusetts

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Massachusetts, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Massachusetts, as well as popular online travel agencies
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Flights Deals

Best Massachusetts Flight Deals from Midway

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

Boston
Bostonnonstop$117
Nantucket
Nantucket2 stops$344
Albany
Albanynonstop$237
Boston
Bostonnonstop$117
Nantucket
Nantucket2 stops$344
Albany
Albanynonstop$237

Cheap Flights from Midway to Massachusetts

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Massachusetts that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Midway to Massachusetts

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to Massachusetts.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southwest Logo
6:30 pm - 9:45 pmMDW-BOS
2h 15mnonstop
Southwest Logo
5:50 am - 7:30 amBOS-MDW
2h 40mnonstop
$117Southwest
Find Deal
Sat, May 10 - Tue, May 13
Southwest Logo
2:50 pm - 10:45 pmMDW-BOS
6h 55m1 stop
Southwest Logo
5:25 am - 7:00 amBOS-MDW
2h 35mnonstop
$127Southwest
Find Deal
Thu, Jun 12 - Tue, Jun 24
Delta Logo
6:00 am - 1:21 pmMDW-BDL
6h 21m1 stop
Delta Logo
5:35 am - 8:39 amBDL-MDW
4h 04m1 stop
$197Delta
Find Deal
Thu, Jul 17 - Tue, Jul 22
Frontier Logo
1:19 pm - 12:44 amMDW-BOS
10h 25m1 stop
Frontier Logo
8:00 am - 12:24 pmBOS-MDW
29h 24m1 stop
$211Frontier
Find Deal
Mon, May 12 - Wed, May 14
Allegiant Air Logo
2:53 pm - 9:17 amMDW-BOS
17h 24m1 stop
Allegiant Air Logo
11:31 am - 7:15 amBOS-MDW
20h 44m1 stop
$214Allegiant Air
Find Deal
Mon, Jun 9 - Thu, Jun 12
Allegiant Air Logo
9:12 am - 12:01 pmMDW-BOS
25h 49m1 stop
Allegiant Air Logo
11:31 am - 7:15 amBOS-MDW
20h 44m1 stop
$215Allegiant Air
Find Deal
Fri, Jun 20 - Sun, Jun 22
Frontier Logo
1:19 pm - 1:05 amMDW-BOS
10h 46m1 stop
Frontier Logo
10:14 am - 10:40 pmBOS-MDW
13h 26m1 stop
$218Frontier
Find Deal
Thu, May 15 - Sun, May 18
Delta Logo
4:15 pm - 12:01 amMDW-ALB
6h 46m1 stop
Delta Logo
6:00 am - 8:41 amALB-MDW
3h 41m1 stop
$245Delta
Find Deal
Wed, Jun 4 - Tue, Jun 10
 Logo
8:09 pm - 9:01 amMDW-BDL
35h 52m3 stops
 Logo
3:54 pm - 7:46 pmBDL-MDW
28h 52m2 stops
Thu, Jun 12 - Sun, Jun 15
 Logo
8:09 pm - 9:01 amMDW-BDL
35h 52m3 stops
 Logo
8:50 am - 2:03 pmBDL-MDW
30h 13m3 stops
Thu, Jun 12 - Sun, Jun 15
Useful Info

KAYAK's insights & trends for Midway to Massachusetts flights

Get data-powered insights and trends into flights from Midway to Massachusetts to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago Midway Airport to Massachusetts flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago Midway Airport to Massachusetts.

The cheapest ticket to Massachusetts from Chicago Midway Airport found in the last 72 hours was to Boston, at $97 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Boston (BOS), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $97.

What is the cheapest month to fly from Chicago Midway Airport to Massachusetts?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Massachusetts, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Massachusetts is January, when tickets cost $185 (return) on average. On the other hand, the most expensive months are February and June, when the average cost of round-trip tickets is $323 and $322 respectively.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Massachusetts?

The average price of all round-trip flights from Chicago Midway Airport to Massachusetts clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Massachusetts on a Saturday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Chicago Midway Airport to Massachusetts. For your return ticket, we recommend flying on a Thursday and avoiding Sundays for the best deals.

How far in advance should I book a flight from Chicago Midway Airport to Massachusetts?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago Midway Airport to Massachusetts, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago Midway Airport to Massachusetts, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.


Good to know

Low seasonJanuary
High seasonOctober
Cheapest flight$59
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly with an average 12% 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 from Chicago Midway Airport to Massachusetts 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 from Chicago Midway Airport to Massachusetts with an airline and back 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 from Chicago Midway Airport to Massachusetts up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Massachusetts?

    The cheapest time of day to fly to Massachusetts is generally in the evening, when round-trip flights cost $230 on average. Morning departures are around 13% more expensive than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $298.

Top tips for finding cheap flights to Massachusetts

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Boston $58 one-way - $157 round-trip

Top 4 airlines serving from Midway to Massachusetts

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Massachusetts. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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
SouthwestOverall score based on 4294 reviews
8.0Comfort
8.2Boarding
7.6Entertainment
7.1Food
8.6Crew
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

Delta is a cut above the others in customer service.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

The worst flight of my life. Never will I fly frontier again

Everything you need to know for your flight from Midway to Massachusetts

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