$63 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 8/18. 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
1 adult, Economy

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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Best Massachusetts Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Bostonnonstop$125
Albany
Albanynonstop$251
Boston
Bostonnonstop$125
Albany
Albanynonstop$251

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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Massachusetts

Tue, Aug 19 - Thu, Aug 21
Southwest Logo
6:10 pm - 9:35 pmMDW-BOS
2h 25mnonstop
Southwest Logo
5:15 am - 6:45 amBOS-MDW
2h 30mnonstop
$125Southwest
Find Deal
Sat, Aug 9 - Thu, Aug 14
Southwest Logo
5:40 pm - 9:00 pmMDW-BOS
2h 20mnonstop
Southwest Logo
5:15 am - 6:45 amBOS-MDW
2h 30mnonstop
$131Southwest
Find Deal
Fri, Aug 1 - Sun, Aug 3
Allegiant Air Logo
2:46 pm - 8:15 amMDW-BOS
16h 29m1 stop
Allegiant Air Logo
11:31 am - 7:13 amBOS-MDW
20h 42m1 stop
$194Allegiant Air
Find Deal
Fri, Aug 1 - Sun, Aug 3
Allegiant Air Logo
2:46 pm - 8:15 amMDW-BOS
16h 29m1 stop
Allegiant Air Logo
11:31 am - 7:13 amBOS-MDW
20h 42m1 stop
$200Allegiant Air
Find Deal
Fri, Aug 29 - Sun, Sep 7
Frontier Logo
9:17 am - 12:08 pmMDW-BOS
25h 51m1 stop
Frontier Logo
9:18 am - 7:39 amBOS-MDW
23h 21m1 stop
$204Frontier
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Sat, Aug 23 - Wed, Sep 3
Delta Logo
6:17 pm - 10:55 pmMDW-BDL
3h 38m1 stop
Delta Logo
5:35 am - 8:35 amBDL-MDW
4h 00m1 stop
$224Delta
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Tue, Jul 1 - Tue, Jul 8
Delta Logo
1:09 pm - 5:42 pmMDW-BDL
3h 33m1 stop
Delta Logo
5:35 am - 8:44 amBDL-MDW
4h 09m1 stop
$227Delta
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Fri, Aug 1 - Sun, Aug 3
 Logo
1:11 pm - 11:03 pmMDW-BOS
32h 52m2 stops
 Logo
11:31 am - 7:13 amBOS-MDW
20h 42m1 stop
Fri, Jul 18 - Sun, Jul 20
 Logo
10:31 am - 9:46 amMDW-BOS
22h 15m1 stop
 Logo
6:10 am - 9:41 amBOS-MDW
28h 31m2 stops
Thu, Jul 24 - Sun, Jul 27
Frontier Logo
9:12 pm - 8:35 amMDW-BOS
10h 23m1 stop
Frontier Logo
6:00 am - 10:24 pmBOS-MDW
17h 24m1 stop
$270Frontier
Find Deal
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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 $104 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 $104.

Can I save money by flying with a layover from Chicago Midway Airport to Massachusetts?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $210, prices are generally cheapest when you fly direct.

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 October, when the average cost of round-trip tickets is $323 and $313 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$63
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly with an average 13% 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 $225 on average. Morning departures are around 11% 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 $293.

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 $68 one-way - $137 round-trip

Top airlines flying 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 4287 reviews
7.1Food
7.6Entertainment
8.2Boarding
8.0Comfort
8.6Crew
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

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

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

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.

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

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