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Find cheap flights from Chicago O'Hare Airport to Massachusetts from $37

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to Massachusetts departing on 8/20. 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
Wed 5/29
Wed 6/5

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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$155
West Tisbury
West Tisbury1 stop$267
Albany
Albanynonstop$271

Good to know

Low season

January

High season

October

Cheapest flight

$37
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from Chicago O'Hare Airport to Boston

FAQs - booking Massachusetts flights

  • How does KAYAK find such low prices on flights from Chicago O'Hare 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 O'Hare Airport to Massachusetts.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Massachusetts from Chicago O'Hare 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 O'Hare 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 O'Hare Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago O'Hare 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 O'Hare 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 4% more expensive 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 5 airlines serving from O'Hare Intl to Massachusetts

 
Need help choosing which airline to fly with from O'Hare Intl 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.
8.3
EVA AirOverall score based on 1556 reviews
8.6crew
8.2comfort
8.0entertainment
7.9food
8.4boarding
Airline reviews

The type of the food requested (Asian vegetarian) was not properly met with. They have very limited snack items that may compensate for the main meals.

8.0 ExcellentAnonymous, Apr 2024TPE - JFK
Read more about EVA Air reviews

The type of the food requested (Asian vegetarian) was not properly met with. They have very limited snack items that may compensate for the main meals.

The quality of the food is pretty good. Thank you, EVA Air.

Pleasant crew. Very long flight, a bit uncomfortable at times being seated, but not too bad.

No ice for the drinks. Only gave a half a cup of your beverage. Not enough water. I got very dehydrated.

Eva air is a good airline. The seats on the way to Taipei could have certainly been more comfortable, but all in all it was a pretty good experience.

Eva is one of the top airlines in Asia... but often are over priced. Finally found a reasonable rate.

My original flight was rescheduled & EVA did a good job rescheduling my flight & connecting flight.

Polite hard working crew. No complaints really. Meals were not to my liking.

Everything was fantastic! The crew really went above and beyond to make it a great flight. I felt cared for with EVA.

t and I Flight crew did excellent job taking care of us and feeding us and staying professional. The boarding was delayed by an hour and then extra security measures were taken. No real explanation except for they said it was more of a maintenance dey

Very comfortable Prem economy seats for a long haul flight. Had a problem with the tv that the crew fixed so was great!

Cathay Pacific seems to be an airline in trouble and on its way out. Lots of broken or poorly functioning things like entertainment screens, seats, and enough well trained staff to handle a full flight. Sad...

The flight crew was exceptionally good. Personal needs were well met. The food choices were very nice.

Excellent. Planes are a little older and could get some refurbishment, but besides that everything was excellent.

While I was in great pain, the seat was sufficiently comfortable to allow me to rest and not be in so much pain.

we were upgraded which was a blessing and tender mercy for us. I fell the day before and was in extreme pain from knee to shoulder. Sitting in a more comfortable seat during the flight was an unexpected blessing and experience.

Seats were very comfortable. Crew were excellent. Food very good.

Flight crew was especially thoughtful and attentive, made sure our seats were comfortable so we could rest on the long flight

I felt thirsty and asked the flight attendent for water, but no one came for more than half an hour.

Everything went smooth. All flights were on time No changing gates, . No changing flights . It was like a completely different airlines tha n the last time I used Cathay Pacific . The last flight, 2 months ago, I had before this one was from Philippines also . I got changed in Manila and was told it only added 2 hours onto my flight . My 20 hour return trip ended up being 30 hours return with a 10.0 hour layover in New York with no seats anywhere . Everyone was sleeping or sitting on the floor . Unlike the hotel I was given in Manila to wait for this flight home . I never thought I would use Cathay Pacific again . But I did and this time you were great! I should have complained about the flight and layover from Hell a couple months ago. Consider that I am complaining about that august/23 flight now . Thank you got the great flying experience on my way home from philippines .

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Everything was good, hard to really comfortable on a flight that long.

Unfortunately our flight was delayed by 45 minutes due to Kate arriving aircraft. Once we stated everything was great.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

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!

Book cheap flights from Chicago to Massachusetts

Recent round-trip flight deals

5/31Fri
1 stop
13h 03mORD-BOS
6/2Sun
1 stop
6h 52mBOS-ORD
$155
5/17Fri
3 stopsSpirit Airlines
24h 59mORD-BOS
5/21Tue
2 stopsSpirit Airlines
31h 00mBOS-ORD
$156
5/13Mon
1 stopFrontier
22h 43mORD-BOS
5/18Sat
2 stopsFrontier
14h 29mBOS-ORD
$163
5/28Tue
nonstopAmerican Airlines
2h 30mORD-BOS
6/5Wed
nonstopAmerican Airlines
3h 06mBOS-ORD
$176
5/31Fri
nonstopAmerican Airlines
2h 30mORD-BOS
6/10Mon
nonstopAmerican Airlines
2h 55mBOS-ORD
$179
5/12Sun
1 stopFrontier
13h 17mORD-BOS
5/15Wed
1 stopFrontier
14h 36mBOS-ORD
$181
5/21Tue
1 stopDelta
7h 49mORD-BOS
5/29Wed
nonstopDelta
2h 55mBOS-ORD
$189
5/10Fri
nonstopDelta
2h 36mORD-BOS
5/11Sat
nonstopDelta
2h 58mBOS-ORD
$194
5/14Tue
1 stopUnited Airlines
4h 25mORD-BOS
5/18Sat
nonstopUnited Airlines
2h 53mBOS-ORD
$242
5/10Fri
nonstopUnited Airlines
2h 21mORD-BOS
5/17Fri
nonstopUnited Airlines
2h 53mBOS-ORD
$247

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Recent one-way flight deals

8/20Tue
nonstopSpirit Airlines
2h 18mORD-BOS
$37
5/15Wed
1 stopSpirit Airlines
10h 16mORD-BOS
$42
5/21Tue
1 stopFrontier
5h 24mORD-BOS
$60
5/29Wed
nonstopDelta
2h 27mORD-BOS
$64
5/31Fri
nonstopUnited Airlines
2h 35mORD-BOS
$70
5/28Tue
1 stopFrontier
5h 24mORD-BOS
$78
7/6Sat
nonstopDelta
2h 31mORD-BOS
$99
5/28Tue
nonstopAmerican Airlines
2h 30mORD-BOS
$113
5/17Fri
nonstopAmerican Airlines
2h 26mORD-BOS
$115
5/27Mon
nonstopUnited Airlines
2h 31mORD-BOS
$120

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Last minute flights from O'Hare Intl to Massachusetts

Last minute flight, train and bus deals

5/4Sat
multi-stop
22h 43mORD-BOS
5/6Mon
multi-stop
13h 54mBOS-ORD
$159
5/4Sat
multi-stopFrontier
22h 43mORD-BOS
5/9Thu
multi-stopFrontier
16h 51mBOS-ORD
$168
5/4Sat
multi-stopSpirit Airlines
10h 25mORD-BOS
5/7Tue
multi-stopSpirit Airlines
19h 39mBOS-ORD
$184
5/4Sat
multi-stopUnited Airlines
4h 25mORD-BOS
5/5Sun
nonstopUnited Airlines
2h 53mBOS-ORD
$218
5/4Sat
multi-stopAmerican Airlines
6h 27mORD-BOS
5/8Wed
nonstopAmerican Airlines
2h 58mBOS-ORD
$232
5/1Wed
multi-stopSpirit Airlines
14h 26mORD-BOS
5/7Tue
multi-stopSpirit Airlines
11h 29mBOS-ORD
$246
5/4Sat
nonstopDelta
2h 29mORD-BOS
5/6Mon
multi-stopDelta
8h 20mBOS-ORD
$263
5/1Wed
multi-stopAmerican Airlines
5h 27mORD-BOS
5/15Wed
nonstopAmerican Airlines
2h 56mBOS-ORD
$277
5/2Thu
multi-stopDelta
5h 37mORD-BOS
5/4Sat
nonstopDelta
3h 04mBOS-ORD
$293
5/2Thu
nonstopUnited Airlines
2h 23mORD-BOS
5/6Mon
nonstopUnited Airlines
2h 48mBOS-ORD
$327

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Chicago O'Hare Airport - Massachusetts Flights