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Find cheap flights from Chicago to Massachusetts from $47

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 5/7. 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
Sun 5/26
Sun 6/2

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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$74
Albany
Albany1 stop$178

Good to know

Low season

January

High season

October

Cheapest flight

$47
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly with an average 2% 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 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 to Massachusetts from Chicago 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 to Massachusetts with an airline and back to Chicago 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 to Massachusetts from Chicago 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 14% cheaper 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 Chicago to Massachusetts

 
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.
8.3
EVA AirOverall score based on 1559 reviews
8.6crew
7.9food
8.0entertainment
8.2comfort
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

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.

For some strange reason I was put in zone 5 for boarding even though I had paid premium price for a premium seat right behind business class. This must have been a flaw because everyone else around me in the same zone (row) had been placed in zone 3.

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!

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Not have to pay for every single item to take a flight. Seating and delays sucked.

Flight was cancelled and I had to spend the night in the airport lugging my suitcase around

If you don’t check in 24 hours in advance, they will charge you $110 to check your bag instead of the $30. I did not get an email with this information and did not check in. In addition, my flight home was cancelled at layover and I had to spend the night in the airport, and then have another layover at another airport before making it home. Will not fly frontier again.

Book cheap flights from Chicago to Massachusetts

Recent round-trip flight deals

6/5Wed
nonstopSpirit Airlines
2h 18mORD-BOS
6/11Tue
nonstopSpirit Airlines
2h 33mBOS-ORD
$74
6/4Tue
1 stopSpirit Airlines
12h 46mORD-BOS
6/11Tue
nonstopSpirit Airlines
2h 33mBOS-ORD
$92
5/11Sat
1 stopFrontier
22h 43mORD-BOS
5/15Wed
1 stopFrontier
14h 36mBOS-ORD
$97
5/11Sat
1 stopFrontier
10h 51mMDW-BOS
5/13Mon
1 stopFrontier
11h 49mBOS-MDW
$98
5/10Fri
nonstopAmerican Airlines
2h 26mORD-BOS
5/15Wed
nonstopAmerican Airlines
2h 56mBOS-ORD
$153
5/10Fri
1 stopAmerican Airlines
4h 15mORD-BOS
5/15Wed
nonstopAmerican Airlines
2h 56mBOS-ORD
$172
5/10Fri
nonstopDelta
2h 36mORD-BOS
5/13Mon
nonstopDelta
2h 54mBOS-ORD
$179
5/9Thu
1 stopUnited Airlines
5h 41mORD-BOS
5/11Sat
nonstopUnited Airlines
2h 53mBOS-ORD
$188
5/31Fri
nonstopUnited Airlines
2h 35mORD-BOS
6/2Sun
nonstopUnited Airlines
2h 50mBOS-ORD
$189
5/10Fri
1 stopDelta
6h 46mORD-ORH
5/12Sun
1 stopDelta
7h 46mORH-ORD
$193

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Recent one-way flight deals

5/7Tue
1 stopSpirit Airlines
7h 35mORD-BOS
$47
5/7Tue
1 stopSpirit Airlines
7h 35mORD-BOS
$48
5/21Tue
1 stopFrontier
5h 24mORD-BOS
$54
5/11Sat
1 stopFrontier
10h 51mMDW-BOS
$55
5/31Fri
nonstopUnited Airlines
2h 35mORD-BOS
$70
5/26Sun
nonstopUnited Airlines
2h 20mORD-BOS
$77
5/10Fri
1 stopDelta
6h 46mORD-ORH
$99
5/25Sat
1 stopAmerican Airlines
6h 24mORD-BOS
$108
6/29Sat
1 stopAmerican Airlines
5h 48mORD-BOS
$109
6/20Thu
nonstopDelta
2h 28mORD-BOS
$119

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Last minute flights from Chicago to Massachusetts

Last minute flight, train and bus deals

4/28Sun
multi-stopFrontier
12h 41mMDW-BOS
5/11Sat
multi-stopFrontier
11h 00mBOS-MDW
$187
4/28Sun
multi-stop
13h 17mORD-BOS
5/7Tue
multi-stop
12h 40mBOS-ORD
$193
4/30Tue
multi-stopSpirit Airlines
21h 45mORD-BOS
5/7Tue
multi-stopSpirit Airlines
9h 41mBOS-ORD
$267
4/28Sun
nonstopDelta
2h 32mORD-BOS
5/9Thu
nonstopDelta
2h 55mBOS-ORD
$269
4/30Tue
multi-stopSpirit Airlines
26h 20mORD-BOS
5/7Tue
multi-stopSpirit Airlines
9h 41mBOS-ORD
$273
4/28Sun
multi-stopDelta
6h 30mORD-BOS
5/9Thu
nonstopDelta
2h 55mBOS-ORD
$278
4/30Tue
nonstopJetBlue
2h 29mORD-BOS
5/5Sun
nonstopJetBlue
2h 53mBOS-ORD
$284
4/29Mon
nonstopJetBlue
2h 29mORD-BOS
5/4Sat
nonstopJetBlue
2h 56mBOS-ORD
$285
4/30Tue
nonstopAmerican Airlines
2h 17mORD-BOS
5/7Tue
multi-stopAmerican Airlines
5h 11mBOS-ORD
$292
4/27Sat
nonstopAmerican Airlines
2h 17mORD-BOS
5/4Sat
multi-stopAmerican Airlines
5h 55mBOS-ORD
$296

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Flights to Massachusetts