$79 Find Cheap Flights from Chicago to Massachusetts - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Massachusetts departing on 9/2. 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, 0 bags

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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Cheap Flights from Chicago to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Bostonnonstop$181
Albany
Albany1 stop$313
Boston
Bostonnonstop$181
Albany
Albany1 stop$313

Book Cheap Chicago 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 Chicago 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 Chicago to Massachusetts

화, 7월 21 - 수, 7월 22
JetBlue Logo
9:40 am - 4:10 pm
ORD
-
MVY
5h 30m
1 stop
JetBlue Logo
5:26 pm - 9:58 pm
MVY
-
ORD
5h 32m
1 stop
$158JetBlue
화, 7월 7 - 화, 7월 14
JetBlue Logo
6:00 am - 3:24 pm
ORD
-
ACK
8h 24m
1 stop
JetBlue Logo
12:02 pm - 5:34 pm
ACK
-
ORD
6h 32m
1 stop
$158JetBlue
월, 8월 10 - 토, 8월 15
Delta Logo
7:55 am - 11:24 am
ORD
-
BOS
2h 29mnonstop
Delta Logo
7:30 am - 9:26 am
BOS
-
ORD
2h 56mnonstop
$181Delta
토, 8월 29 - 토, 9월 12
Delta Logo
7:30 am - 10:59 am
ORD
-
BOS
2h 29mnonstop
Delta Logo
1:10 pm - 3:07 pm
BOS
-
ORD
2h 57mnonstop
$182Delta
토, 7월 18 - 일, 8월 2
Southwest Logo
5:45 pm - 9:10 pm
MDW
-
BOS
2h 25mnonstop
Southwest Logo
10:05 pm - 11:50 pm
BOS
-
MDW
2h 45mnonstop
$182Southwest
월, 9월 14 - 화, 9월 15
Southwest Logo
5:45 am - 9:00 am
MDW
-
BOS
2h 15mnonstop
Southwest Logo
8:15 am - 1:05 pm
BOS
-
MDW
5h 50m
2 stops
$183Southwest
금, 7월 10 - 월, 7월 20
United Airlines Logo
7:45 pm - 11:21 pm
ORD
-
BOS
2h 36mnonstop
United Airlines Logo
8:15 pm - 10:15 pm
BOS
-
ORD
3h 00mnonstop
$187United Airlines
토, 7월 4 - 금, 7월 10
American Airlines Logo
5:00 am - 4:51 pm
ORD
-
ORH
10h 51m
1 stop
American Airlines Logo
5:16 pm - 12:29 am
ORH
-
ORD
8h 13m
1 stop
$196American Airlines
화, 6월 23 - 토, 6월 27
American Airlines Logo
6:29 am - 4:53 pm
ORD
-
ORH
9h 24m
1 stop
American Airlines Logo
5:18 pm - 6:56 am
ORH
-
ORD
14h 38m
1 stop
$220American Airlines
일, 10월 4 - 토, 10월 10
United Airlines Logo
6:10 pm - 9:22 pm
ORD
-
ALB
2h 12mnonstop
United Airlines Logo
6:00 am - 7:33 am
ALB
-
ORD
2h 33mnonstop
$326United Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Massachusetts flights

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

How much is a round-trip flight from Chicago to Massachusetts?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Massachusetts departing in August.

What is the cheapest Chicago to Massachusetts flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Massachusetts from Chicago found in the last 5 days was to Boston, at $173 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Boston (BOS), and the cheapest round-trip airline ticket found on this route in the last 5 days was $173.

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

The average price for all round-trip flights from Chicago to Massachusetts depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Massachusetts is generally at night, when round-trip flights cost $224 on average. Morning departures are around 15% cheaper than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally in the evening, which is peak travel time and where the average cost of a ticket is $299.

Can I save money by flying with a layover from Chicago 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $332 on average.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago 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 to Massachusetts is November, when tickets cost $182 (return) on average. On the other hand, the most expensive months are December and January, when the average cost of round-trip tickets is $279 and $248 respectively.

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

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

If you are looking for a flight deal from Chicago to Massachusetts, look for departures on Thursdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Massachusetts, Friday is the cheapest day to fly and Sunday is the most expensive.

How far in advance should I book a flight from Chicago 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 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 to Massachusetts, you should book around 2 weeks before departure, which saves you about 28% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$79
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Chicago to West Tisbury

FAQs - booking Massachusetts flights

  • How does KAYAK find such low prices on flights from Chicago 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 to Massachusetts.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Massachusetts?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago 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 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 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 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 to Massachusetts up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from Chicago 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 Chicago 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.
7.9
SouthwestOverall score based on 4235 reviews
7.0Food
8.6Crew
7.5Entertainment
8.0Comfort
8.1Boarding
Airline reviews

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

10.0 ExcellentAnonymous, Jun 2026
OKC - LAS
Read more Southwest reviews

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

Arrived early, comfortable seats (Comfort+). Mediocre food, poor wifi (intermittent).

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Flight was great! This flight from Atlanta was even better than when I paid for Comfort from SNA to Atlanta.

Connection flights should be spaced out farther because too close I missed my connection.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Average seat comfort, a drink and chips were provided, early boarding because we checked a carryon at the gate was nice. Ticket pricing shenanigans, including fees to pick a seat, check a bag, and get food onboard - evidence the industry is reinvigorating last century’s strategies- destroys the experience before one ever arrives at the airport. It’s difficult to recognize any value or sustain loyalty in the end-to-end process making air travel more drudgery than pleasure.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

It wa sort of on time; the cab was left with some trash

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

Nice plane, clean, wifi available and movies. All the flight attendants were courteous.

The gate attendant in Boston had a high raspy voice and spoke much too fast to be understood. Not pleasant.

This was the first flight I've taken since pre-pandemic. I was pleased with how orderly the boarding and disembarking went. The seats were comfortable. I loved that there was no "first class'. The attendants and passengers I met were all very friendly and welcoming.

Boarding was extremely slow and disorganized. Onboard crew was unfriendly.

There was a screen but no earphones that could use the older input so I could listen to anything.

Jet blue just had great service overall! Only a little turbulence heading out of Austin, otherwise the jet stream helped the speed of the trip!

Boarding was quick and efficient. The flight crew were friendly. There were limited food options available on the flight. The pocket guide said there would be salad and sandwich sections available on flights over 3.5 hours. The only food available were snack boxes. And those were limited as well. My flight was over 5 hours. The entertainment system worked well. I had both extra legroom seats and regular coach seats. The seats were not very comfortable. The entertainment controls in the armrest made it difficult to rest my arm without changing the channel on my neighbors TV. Overall, my experience was mediocre.

Boarding was fast, easy, and we landed early. The entertainment system was very buggy and kept resetting throughout the flight.

I purchased ticket so our daughter ( a minor) can sit next to her mother. No help at gate after kayak insisted that this could be done. She ended sitting by herself

Terrible. There was a lot of misleading information regarding ticketing, seat upgrades, & boarding group. I also expect my seat will recline. I have back problems & it is very painful for me of the seat doesn’t recline. In addition, when I choose a fare that allows me a carry-on bag, I expect to be able to carry it on. Not be forced to check it. Thos happened on my flight to MCO & back to Boston. Not sure I will ever fly JetBlue again. Further I bought the ticket through hat deal. I will NEVER do that again. They were incapable of providing an accurate record locator # for either leg of the trip. I had to call them before each flight with me VERY stressed about whether I would actually be able to get on my flight. Who does that? Who books flight & then FAILS to give an accurate record locator? Twice!

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

Cabin class types available on flights to Massachusetts

Cabin classes available on flights to Massachusetts. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.