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Find cheap flights from Chicago O'Hare Airport to Massachusetts from $30

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 6/27. 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
Thu 6/27
Thu 7/4

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Best Massachusetts Flight Deals

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

Boston
Bostonnonstop$146
Nantucket
Nantucketnonstop$224
West Tisbury
West Tisbury1 stop$223
Albany
Albanynonstop$215

Good to know

Low season

January

High season

May

Cheapest flight

$30
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly with an average 5% 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 1% 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 1502 reviews
8.6Crew
8.0Entertainment
8.2Comfort
7.9Food
8.4Boarding
Airline reviews

Their announcement was not quite clear in Chinese. The rest is pretty good.

8.0 ExcellentYue, May 2024IAH - TPE
Read more about EVA Air reviews

Their announcement was not quite clear in Chinese. The rest is pretty good.

The hygiene of the bathrooms were terrible. Urine smells leaked out into the cabin and the seats were really tight, even for a petite woman like myself. Flight attendants did not go through the cabin enough to offer refreshments.

I was expecting that movie selection and food would have been better. Everything else was great.

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.

Great, the flight attendants were very friendly and the food was also good.

The overall flight went well and the aircrew was pleasant.

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

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

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.

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.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

My flight was cancelled!!! I had to spend 200.00 on another flight!!

Worst airline experience ever. Lost my IPad going thru security. Charged for my dog carriage at the gate not at ticket counter. Gave away my seat 6D. Expressed I wanted my seat back after charging me 99 for dog carriage. Should have thrown it out. Had a 16 yr old Yorkie heading to Boston after being a snowbird. Seats small. Very bad experience. Still don’t have my IPad. Horrible

Flight delayed then canceled! I will NEVER fly Spirit Airlines again and will tell all my friends!

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.

Book cheap flights from Chicago to Massachusetts

Recent round-trip flight deals

9/10Tue
1 stopSpirit Airlines
4h 45mORD-BDL
9/11Wed
1 stopSpirit Airlines
5h 32mBDL-ORD
$118
6/12Wed
1 stopSpirit Airlines
5h 26mORD-BDL
6/18Tue
1 stopSpirit Airlines
5h 18mBDL-ORD
$128
6/11Tue
nonstopAmerican Airlines
2h 26mORD-BOS
6/12Wed
nonstopAmerican Airlines
2h 55mBOS-ORD
$157
6/11Tue
nonstopUnited Airlines
2h 31mORD-BOS
8/30Fri
nonstopUnited Airlines
2h 47mBOS-ORD
$167
6/30Sun
1 stopFrontier
11h 14mORD-BOS
7/9Tue
1 stopFrontier
5h 44mBOS-ORD
$168
6/4Tue
nonstopAmerican Airlines
2h 26mORD-BOS
6/9Sun
nonstopAmerican Airlines
2h 55mBOS-ORD
$170
7/6Sat
nonstopDelta
2h 33mORD-BOS
7/9Tue
nonstopDelta
3h 01mBOS-ORD
$189
7/12Fri
1 stopDelta
4h 49mORD-ORH
7/15Mon
1 stopDelta
6h 58mORH-ORD
$212
7/3Wed
nonstopUnited Airlines
2h 05mORD-ALB
7/4Thu
nonstopUnited Airlines
2h 27mALB-ORD
$215
6/13Thu
1 stopFrontier
9h 07mORD-BDL
6/17Mon
1 stopFrontier
12h 02mBDL-ORD
$224

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Recent one-way flight deals

6/27Thu
nonstopSpirit Airlines
2h 28mORD-BOS
$30
7/17Wed
nonstopSpirit Airlines
2h 28mORD-BOS
$31
6/4Tue
1 stopFrontier
5h 12mORD-BOS
$58
8/14Wed
1 stopFrontier
5h 45mORD-BOS
$68
6/11Tue
nonstopUnited Airlines
2h 31mORD-BOS
$79
8/29Thu
nonstopDelta
2h 26mORD-BOS
$89
7/31Wed
1 stopDelta
4h 49mORD-ORH
$104
6/3Mon
nonstopUnited Airlines
2h 35mORD-BOS
$107
6/19Wed
nonstopAmerican Airlines
2h 14mORD-ALB
$115
7/28Sun
nonstopAmerican Airlines
2h 27mORD-BOS
$119

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Last minute flights from O'Hare Intl to Massachusetts

Last minute flight, train and bus deals

5/30Thu
multi-stop
5h 09mORD-BOS
6/4Tue
multi-stop
10h 17mBOS-ORD
$129
6/2Sun
multi-stop
19h 54mORD-BOS
6/5Wed
multi-stop
12h 30mBOS-ORD
$133
6/2Sun
multi-stopSpirit Airlines
11h 14mORD-BOS
6/5Wed
multi-stopSpirit Airlines
12h 38mBOS-ORD
$186
6/2Sun
multi-stopSpirit Airlines
11h 14mORD-BOS
6/12Wed
nonstopSpirit Airlines
2h 54mBOS-ORD
$187
6/1Sat
multi-stopAmerican Airlines
5h 16mORD-BOS
7/3Wed
nonstopAmerican Airlines
2h 55mBOS-ORD
$245
5/31Fri
nonstopAmerican Airlines
2h 15mORD-BOS
6/10Mon
nonstopAmerican Airlines
2h 55mBOS-ORD
$247
6/2Sun
nonstopUnited Airlines
2h 20mORD-BOS
6/4Tue
multi-stopUnited Airlines
5h 10mBOS-ORD
$260
5/29Wed
multi-stopDelta
7h 19mORD-BOS
6/3Mon
nonstopDelta
2h 55mBOS-ORD
$280
6/2Sun
nonstopUnited Airlines
2h 31mORD-BOS
6/17Mon
nonstopUnited Airlines
2h 44mBOS-ORD
$296
5/31Fri
multi-stopDelta
5h 36mORD-ORH
6/3Mon
multi-stopDelta
7h 46mORH-ORD
$302

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