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Find cheap flights from Chicago to Massachusetts from $42

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 6/26. 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
Mon 6/10
Mon 6/17

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Best Massachusetts Flight Deals

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

Boston
Boston2 stops$159
Albany
Albany1 stop$257

Good to know

Low season

January

High season

October

Cheapest flight

$42
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly and prices are also 1% 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 12% 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 1522 reviews
8.6Crew
7.9Food
8.4Boarding
8.2Comfort
8.0Entertainment
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.

Fast and efficient boarding. Flight was on time. Service was very good for our long flight. First time flying with this airline and I would highly recommend.

Eva Air's Business Class is pretty decent. With the given price, I think that the food can be better.

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.

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.

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

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 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.

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.

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Book cheap flights from Chicago to Massachusetts

Recent round-trip flight deals

5/30Thu
1 stopFrontier
10h 17mMDW-BDL
6/4Tue
1 stopFrontier
6h 46mBDL-MDW
$143
5/30Thu
1 stopFrontier
10h 17mMDW-BDL
6/5Wed
1 stopFrontier
14h 52mBDL-MDW
$153
5/22Wed
2 stopsSpirit Airlines
23h 27mORD-BOS
5/26Sun
1 stopSpirit Airlines
12h 30mBOS-ORD
$159
6/10Mon
2 stopsSpirit Airlines
17h 18mORD-BOS
6/17Mon
1 stopSpirit Airlines
7h 44mBOS-ORD
$161
5/31Fri
nonstopDelta
2h 36mORD-BOS
6/5Wed
nonstopDelta
2h 55mBOS-ORD
$163
5/29Wed
nonstopDelta
2h 36mORD-BOS
6/8Sat
nonstopDelta
2h 58mBOS-ORD
$173
7/1Mon
nonstopAmerican Airlines
2h 26mORD-BOS
7/5Fri
nonstopAmerican Airlines
2h 57mBOS-ORD
$183
7/1Mon
1 stopAmerican Airlines
4h 05mORD-BOS
7/5Fri
nonstopAmerican Airlines
2h 56mBOS-ORD
$197
5/24Fri
nonstopUnited Airlines
2h 35mORD-BOS
5/27Mon
nonstopUnited Airlines
2h 50mBOS-ORD
$204
5/15Wed
nonstopUnited Airlines
2h 23mORD-BOS
5/26Sun
nonstopUnited Airlines
2h 50mBOS-ORD
$253

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Recent one-way flight deals

6/26Wed
nonstopSpirit Airlines
2h 29mORD-BOS
$42
6/14Fri
nonstopSpirit Airlines
2h 28mORD-BOS
$43
5/18Sat
1 stopFrontier
14h 47mORD-BOS
$56
9/3Tue
1 stopFrontier
5h 45mORD-BOS
$57
7/2Tue
nonstopAmerican Airlines
2h 26mORD-BOS
$69
5/29Wed
1 stopDelta
5h 36mORD-ORH
$104
5/18Sat
1 stopUnited Airlines
6h 28mORD-BOS
$108
5/28Tue
nonstopUnited Airlines
2h 31mORD-BOS
$111
6/4Tue
nonstopAmerican Airlines
2h 26mORD-BOS
$114
7/31Wed
1 stopDelta
4h 49mORD-ORH
$118

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Last minute flights from Chicago to Massachusetts

Last minute flight, train and bus deals

5/16Thu
multi-stop
19h 54mORD-BOS
5/22Wed
multi-stop
11h 25mBOS-ORD
$138
5/16Thu
multi-stop
19h 54mORD-BOS
5/26Sun
multi-stop
12h 30mBOS-ORD
$156
5/16Thu
multi-stopFrontier
19h 54mORD-BOS
5/19Sun
multi-stopFrontier
15h 25mBOS-ORD
$159
5/15Wed
multi-stopFrontier
24h 01mORD-BOS
5/20Mon
multi-stopFrontier
16h 04mBOS-ORD
$173
5/16Thu
multi-stopSpirit Airlines
13h 02mORD-BOS
5/21Tue
multi-stopSpirit Airlines
23h 05mBOS-ORD
$215
5/16Thu
multi-stopSpirit Airlines
10h 11mORD-BOS
5/21Tue
multi-stopSpirit Airlines
23h 05mBOS-ORD
$221
5/15Wed
nonstopUnited Airlines
2h 23mORD-BOS
5/26Sun
nonstopUnited Airlines
2h 50mBOS-ORD
$253
5/15Wed
multi-stopUnited Airlines
5h 30mORD-BOS
5/26Sun
nonstopUnited Airlines
2h 50mBOS-ORD
$262
5/15Wed
multi-stopAmerican Airlines
4h 44mORD-BOS
5/29Wed
nonstopAmerican Airlines
2h 59mBOS-ORD
$287
5/16Thu
multi-stopAmerican Airlines
4h 44mORD-BOS
5/22Wed
nonstopAmerican Airlines
2h 56mBOS-ORD
$291

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Flights to Massachusetts