$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 9/3. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Booking Insights
Flights Deals

Cheap Flights from Midway to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Bostonnonstop$127
Albany
Albanynonstop$217
Boston
Bostonnonstop$127
Albany
Albanynonstop$217

Book Cheap Midway to Massachusetts Plane Tickets

 
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

Thu, Sep 4 - Sun, Sep 7
Southwest Logo
6:45 am - 10:00 amMDW-BOS
2h 15mnonstop
Southwest Logo
5:30 am - 7:05 amBOS-MDW
2h 35mnonstop
$127Southwest
Find Deal
Thu, Sep 4 - Wed, Sep 10
Southwest Logo
2:35 pm - 11:00 pmMDW-BOS
7h 25m1 stop
Southwest Logo
9:25 am - 11:05 amBOS-MDW
2h 40mnonstop
$137Southwest
Find Deal
Thu, Sep 4 - Sun, Sep 7
Southwest Logo
1:45 pm - 4:50 pmMDW-BDL
2h 05mnonstop
Southwest Logo
5:35 am - 6:55 amBDL-MDW
2h 20mnonstop
$137Southwest
Find Deal
Tue, Sep 2 - Sat, Sep 6
Southwest Logo
6:25 am - 3:25 pmMDW-BOS
8h 00m1 stop
Southwest Logo
5:50 am - 7:25 amBOS-MDW
2h 35mnonstop
$142Southwest
Find Deal
Tue, Sep 9 - Thu, Sep 11
Delta Logo
4:25 pm - 11:58 pmMDW-BDL
6h 33m1 stop
Delta Logo
5:35 am - 8:40 amBDL-MDW
4h 05m1 stop
$197Delta
Find Deal
Thu, Aug 14 - Sat, Aug 16
Frontier Logo
9:12 pm - 8:35 amMDW-BOS
10h 23m1 stop
Frontier Logo
9:40 am - 8:22 pmBOS-MDW
11h 42m1 stop
$208Frontier
Find Deal
Fri, Sep 26 - Sat, Oct 4
Frontier Logo
6:21 am - 8:11 amMDW-BOS
24h 50m1 stop
Frontier Logo
8:56 am - 12:44 pmBOS-MDW
28h 48m1 stop
$209Frontier
Find Deal
Sat, Sep 13 - Sun, Sep 14
Delta Logo
1:08 pm - 5:37 pmMDW-BDL
3h 29m1 stop
Delta Logo
5:35 am - 8:40 amBDL-MDW
4h 05m1 stop
$217Delta
Find Deal
Sun, Aug 17 - Thu, Aug 21
Frontier Logo
3:58 pm - 12:38 amMDW-BOS
7h 40m1 stop
Frontier Logo
9:37 am - 1:10 pmBOS-MDW
4h 33m1 stop
$218Frontier
Find Deal
Wed, Nov 5 - Wed, Nov 12
Delta Logo
9:35 am - 4:05 pmMDW-ALB
5h 30m1 stop
Delta Logo
6:00 am - 8:45 amALB-MDW
3h 45m1 stop
$237Delta
Find Deal
Booking Insights

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 $110 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 $110.

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 $207, 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 Wednesday 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, which saves you about 22% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.


Good to know

Low seasonJanuary
Cheapest flight$59
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 $222 on average. Morning departures are around 12% 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 $283.

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

Reviews of the 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 4241 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

2.0 MediocreAnonymous, Jul 2025AUS - RDU
Read more Southwest reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

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

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.