$115 Find Cheap Flights from Chicago to Massachusetts - Compare and Save

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Cheap Flights from Chicago to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Boston
Boston1 stop$217
Nantucket
Nantucket1 stop$565
Albany
Albany1 stop$262
Boston
Boston1 stop$217
Nantucket
Nantucket1 stop$565
Albany
Albany1 stop$262
Booking Insights

KAYAK's insights & trends for Chicago to Massachusetts flights

Get data-powered insights and trends into flights from Chicago to Massachusetts to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to Massachusetts?

Flight prices are typical for this route right now.

Flights to Massachusetts from Chicago usually cost between $213 and $324 in October.
The lowest price found in the past 5 days was $217 on JetBlue (Oct 22-Oct 24).

What is the cheapest Chicago to Massachusetts flight route?

The cheapest ticket to Massachusetts from Chicago found in the last 5 days was to Boston, at $166 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Boston (BOS), and the cheapest round-trip airline ticket found on this route in the last 5 days was $166.

What is the cheapest time of day to fly to Massachusetts?

The cheapest time of day to fly to Massachusetts is generally at night, when round-trip flights cost $239 on average. Morning departures are around 14% cheaper than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally in the evening, which is peak travel time and where the average cost of a ticket is $313.

Can I save money by flying with a layover from Chicago to Massachusetts?

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $286 on average.

What is the cheapest month to fly from Chicago to Massachusetts?

The cheapest month for flights from Chicago to Massachusetts is January, when tickets cost $200 (return) on average. On the other hand, the most expensive months are August and June, when the average cost of round-trip tickets is $294 and $280 respectively.

What’s the cheapest day of the week to fly from Chicago to Massachusetts?

If you are looking for a flight deal from Chicago to Massachusetts, look for departures on Saturdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Massachusetts, Friday is the cheapest day to fly and Sunday is the most expensive.

How far in advance should I book a flight from Chicago to Massachusetts?

To get a below average price on the flight from Chicago to Massachusetts, you should book around 3 weeks before departure, which saves you about 27% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Good to know

Low season

January

Cheapest flight

$115
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from Chicago Midway 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 from Chicago to Massachusetts 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 from Chicago to Massachusetts with an airline and back 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 from Chicago to Massachusetts up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the 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.
8.0
SouthwestOverall score based on 4195 reviews
8.1Boarding
8.6Crew
7.0Food
7.5Entertainment
8.0Comfort
Airline reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

10.0 ExcellentDenis, Aug 2026
Read more Southwest reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

The plane was a rather tired 737-800, with old style small luggage bins. Poor air flow. USB charger in the infotainment system was not functioning. The flight was 2 hours late due to crew rest requirements (not their fault). On arrival in Seattle, waited on the tarmac for 30 minutes with very few updates from the crew.

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

It was very cold because the air conditioner was on high power, and my son got sick.

Terrible service - they don’t want to be there and bad food. Entertainment system in economy from the 2000s

No drink service but there was no N/A as an option to choose. Seats were extremely tight. I am under 5.5 and I bumped my knees have no idea how taller people could manage.

Flight delayed, last seat on the plane, no arrival Gate available due to the plane departing late

Kayak booked this flight with only 1h 20min layover in Chicago. This made it impossible for me and several other passengers to reach this flight. Moreover, the gate closed boarding in spite of several passengers still on their way without waiting even one more minute. However, the plane departed with 20min (!) delay, i.e., there would have been at least 15 min time to let the delayed passengers board without causing any delays. I complained and as a "thank you" the attendent booked us on the last (!) flight to Indianapolis ~7h later! Thankfully, I caught the spitefulness and the United customer line rebooked the flight to an earlier flight. Although I can't grade this particular flight since I never had a chance to take it, Kayak made the mistake of a too short layover and the crew at the gate was awful.

Flight did not have wifi service. It was experiencing technical difficulties. Definitely and old plane that needs updating.

Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.

It was a good experience, unfortunately my checked baggages were come late and not arrived on time.

Very stressful to locate United Airline boarding area, delayed flight, changing boarding area again to another location with all tiredness 😩. But flying was fine.

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

Super friendly with lots of drink options an entertainment. Friendly crew.

AA was fine....the overall experience was subpar, but not due to the airline due to broader issues

No ground air conditioner for the plane. Very hot and humid prior to take off which was an uncomfortable period of time.

Check-in process was poor, very poor, only one person to check-in all passengers, so if one passenger had a check-in issue, all other passengers were delayed. All check-ins should have two airline staff to check-in passengers.

The flight up was great no issues. The flight back home was a cluster. I was told the plane I was waiting on was giving to another flight which caused me to miss my connection flight. Granted the airline did great with getting hotel and vouchr for food.

Flight was delayed and so much of inconvenience related to the gate change.

Nothing was good about this flight. Although the flight actually departed more than 3 hours late, due to “air traffic control management” we pushed back from gate 2 hours and 20 minutes late and proceeded to sit 100 yards from gate for and then n tarmac for another 1/2 hour additional 20 minutes

Couldn't make the flight because connecting flight was canceled.

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

The plane was freezing cold. Normally I’m fine on planes but I needed to toss a sweatshirt on this time.

Very good flight that left on time and arrived earlier than anticipated, which was a plus! The crew members were very welcoming and helpful. However, the temperature on the flight was very cold - almost to the point of extreme discomfort. Additionally, requiring passengers to pay $8 for headphones to access the JetBlue entertainment was disappointing. Those earbud jacks are not used with most technology and would not be able to be used. There was no option to use Bluetooth for my own earbuds. Beyond those inconveniences, the flight was good.

Separated a pair of family members(father and teenage daughter) on all legs of the flight that were booked together, just to create an upsell. Food was horrible and only catered to vegetarians and gluten free crowd. I’d rather give more of my money to another straight shooting airline.

A nightmare. Scheduled flight delayed 2 hours then cancelled because pilot timed out . Unable to find another pilot. Really?! Weather certainly a factor, but JetBlue seemed totally unprepared for the chaos that ensued when flight routes were cancelled. More cancelled flights, finally many of us who had been bumped from other flights were allowed to board a Boston bound plane around 3:00am, delay after delay, sat on tarmac for another half hour while pilot dealt with weight distribution issues (?), arrived in Boston 4:30. Crew were wonderful- same attendants all day and night and they were exhausted. Fortunately for me and my son that Boston was our final destination, not so lucky for many who missed connecting flights.

The flight was delayed 14 hours and communication was very poor. No one seemed to know what was happening and the gate agent was trying to help people for several flights. She was by herself trying to help 100s of people.

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

My bag was not loaded on my flight. it was not communicated to me until i was waiting for my bag at my destination. there was no confirmation of when my bag was arriving and no way to track it.

This was the first flight I've taken since pre-pandemic. I was pleased with how orderly the boarding and disembarking went. The seats were comfortable. I loved that there was no "first class'. The attendants and passengers I met were all very friendly and welcoming.

There was a screen but no earphones that could use the older input so I could listen to anything.

Jet blue just had great service overall! Only a little turbulence heading out of Austin, otherwise the jet stream helped the speed of the trip!

More options for your flight from Chicago to Massachusetts

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