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Find cheap flights from Chicago to Massachusetts from $33

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 8/28. 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 7/11
Thu 7/18

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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$50
Nantucket
Nantucket1 stop$218
Albany
Albanynonstop$125

Good to know

Low season

January

High season

October

Cheapest flight

$33
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly and prices are also 0% lower on average.
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 19% 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.
7.8
Cathay PacificOverall score based on 1029 reviews
7.8Comfort
7.5Food
8.0Boarding
8.2Crew
8.0Entertainment
Airline reviews

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

10.0 ExcellentAnonymous, May 2024LAX - HKG
Read more about Cathay Pacific reviews

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

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

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.

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

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

The plane was not on time for boarding or departure or arrivals.

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

Did not realize seats did not recline. Best to travel in an exit row... No question

I strongly dislike Frontier. I find them barebones, the seats not particularly comfortable, the nickel and diming is maddening, the app is TERRIBLE - super confusing to navigate, and the last 4 frontier flights I have flown have been on AVERAGE 2 hours late, one ruining a fancy night out in Vegas with reservations made well in advance, which was nodded to with a measly 5000 miles, which translates to almost nothing. At least credit a free checked bag or something.

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

Book cheap flights from Chicago to Massachusetts

Recent round-trip flight deals

8/21Wed
nonstopSpirit Airlines
2h 28mORD-BOS
8/28Wed
1 stopSpirit Airlines
8h 54mBOS-ORD
$64
6/24Mon
nonstopSpirit Airlines
2h 28mORD-BOS
6/26Wed
nonstopSpirit Airlines
2h 54mBOS-ORD
$65
8/7Wed
1 stopFrontier
8h 58mMDW-BOS
8/14Wed
1 stopFrontier
7h 37mBOS-MDW
$121
8/7Wed
1 stopFrontier
8h 58mMDW-BOS
8/17Sat
1 stopFrontier
7h 25mBOS-MDW
$123
8/20Tue
nonstopUnited Airlines
2h 03mORD-ALB
8/28Wed
nonstopUnited Airlines
2h 25mALB-ORD
$125
8/6Tue
nonstopDelta
2h 26mORD-BOS
8/14Wed
nonstopDelta
2h 59mBOS-ORD
$137
9/19Thu
nonstopUnited Airlines
2h 03mORD-ALB
9/24Tue
1 stopUnited Airlines
4h 36mALB-ORD
$149
9/10Tue
nonstopAmerican Airlines
2h 21mORD-ALB
9/17Tue
nonstopAmerican Airlines
2h 32mALB-ORD
$153
8/20Tue
1 stopAmerican Airlines
7h 17mORD-ALB
8/28Wed
nonstopAmerican Airlines
2h 30mALB-ORD
$163
9/18Wed
1 stopDelta
6h 14mORD-ALB
9/25Wed
1 stopDelta
4h 08mALB-ORD
$176

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Recent one-way flight deals

8/28Wed
1 stopSpirit Airlines
10h 59mORD-BOS
$33
6/18Tue
1 stopSpirit Airlines
11h 43mORD-BOS
$34
8/21Wed
1 stopFrontier
5h 45mORD-BOS
$47
8/14Wed
1 stopFrontier
5h 45mORD-BOS
$48
8/15Thu
nonstopDelta
2h 26mORD-BOS
$56
9/7Sat
nonstopUnited Airlines
2h 09mORD-ALB
$63
8/31Sat
nonstopUnited Airlines
2h 15mORD-BDL
$63
8/17Sat
nonstopDelta
2h 28mORD-BOS
$69
9/7Sat
1 stopAmerican Airlines
4h 32mORD-ALB
$86
8/17Sat
nonstopAmerican Airlines
2h 04mORD-BDL
$95

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Last minute flights from Chicago to Massachusetts

Last minute flight, train and bus deals

6/15Sat
multi-stopSpirit Airlines
7h 16mORD-BOS
6/17Mon
nonstopSpirit Airlines
2h 54mBOS-ORD
$111
6/12Wed
multi-stopSpirit Airlines
12h 02mORD-BOS
6/17Mon
nonstopSpirit Airlines
2h 54mBOS-ORD
$114
6/14Fri
multi-stopFrontier
13h 58mMDW-BOS
6/18Tue
multi-stopFrontier
9h 38mBOS-MDW
$158
6/14Fri
multi-stopFrontier
13h 58mMDW-BOS
6/17Mon
multi-stopFrontier
6h 49mBOS-MDW
$188
6/16Sun
nonstopDelta
2h 28mORD-BOS
6/19Wed
nonstopDelta
2h 57mBOS-ORD
$234
6/13Thu
nonstopDelta
2h 28mORD-BOS
6/18Tue
nonstopDelta
2h 45mBOS-ORD
$250
6/16Sun
nonstopAmerican Airlines
2h 18mORD-BOS
6/16Sun
multi-stopAmerican Airlines
5h 24mBOS-ORD
$325
6/12Wed
multi-stopUnited Airlines
5h 04mORD-BOS
6/16Sun
multi-stopUnited Airlines
5h 30mBOS-ORD
$372
6/12Wed
multi-stopAmerican Airlines
5h 36mORD-BOS
6/12Wed
nonstopAmerican Airlines
2h 57mBOS-ORD
$387
6/16Sun
multi-stopUnited Airlines
12h 46mORD-BOS
6/19Wed
multi-stopUnited Airlines
7h 53mBOS-ORD
$460

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Flights to Massachusetts