$53 Find Cheap Flights from Chicago to Massachusetts

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 10/16. 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.
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KAYAK searches hundreds of travel sites at once for deals on flights to Massachusetts

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Massachusetts.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Massachusetts.
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Best Massachusetts Flight Deals from Chicago

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

Boston
Boston1 stop$109
Nantucket
Nantucket1 stop$190
Albany
Albanynonstop$225
Boston
Boston1 stop$109
Nantucket
Nantucket1 stop$190
Albany
Albanynonstop$225

Cheap Flights from Chicago to Massachusetts

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Massachusetts that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Chicago to Massachusetts

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to Massachusetts.
Discover the best prices for you by selecting your travel dates on KAYAK.
Spirit Airlines Logo
7:37 am - 9:50 pmORD-BOS
13h 13m1 stop
Spirit Airlines Logo
3:49 pm - 11:04 pmBOS-ORD
8h 15m1 stop
$109Spirit Airlines
Find Deal
Wed, Jun 4 - Wed, Jun 11
JetBlue Logo
4:51 pm - 8:27 pmORD-BOS
2h 36mnonstop
JetBlue Logo
6:00 am - 7:55 amBOS-ORD
2h 55mnonstop
$117JetBlue
Find Deal
Fri, Jun 20 - Mon, Jun 23
Southwest Logo
6:30 pm - 9:45 pmMDW-BOS
2h 15mnonstop
Southwest Logo
5:50 am - 7:30 amBOS-MDW
2h 40mnonstop
$117Southwest
Find Deal
Sat, May 10 - Tue, May 13
American Airlines Logo
8:40 pm - 12:20 amORD-BOS
2h 40mnonstop
American Airlines Logo
12:42 pm - 2:37 pmBOS-ORD
2h 55mnonstop
$118American Airlines
Find Deal
Fri, Jun 6 - Wed, Jun 11
United Airlines Logo
7:53 pm - 11:20 pmORD-BOS
2h 27mnonstop
United Airlines Logo
6:59 pm - 11:37 pmBOS-ORD
5h 38m1 stop
$123United Airlines
Find Deal
Tue, Jun 3 - Tue, Aug 12
Southwest Logo
2:50 pm - 10:45 pmMDW-BOS
6h 55m1 stop
Southwest Logo
5:25 am - 7:00 amBOS-MDW
2h 35mnonstop
$127Southwest
Find Deal
Thu, Jun 12 - Tue, Jun 24
United Airlines Logo
7:54 pm - 11:21 pmORD-BOS
2h 27mnonstop
United Airlines Logo
6:00 am - 7:58 amBOS-ORD
2h 58mnonstop
$134United Airlines
Find Deal
Wed, May 28 - Thu, May 29
Delta Logo
7:00 am - 10:25 amORD-BOS
2h 25mnonstop
Delta Logo
7:15 am - 9:09 amBOS-ORD
2h 54mnonstop
$137Delta
Find Deal
Sat, May 31 - Wed, Jun 4
American Airlines Logo
6:30 am - 9:52 amORD-BOS
2h 22mnonstop
American Airlines Logo
5:00 am - 6:54 amBOS-ORD
2h 54mnonstop
$149American Airlines
Find Deal
Sun, Jun 8 - Thu, Jun 12
Delta Logo
7:00 am - 10:31 amORD-BOS
2h 31mnonstop
Delta Logo
7:20 am - 9:18 amBOS-ORD
2h 58mnonstop
$158Delta
Find Deal
Fri, Jul 4 - Fri, Jul 11
Useful Info

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.

What is the cheapest Chicago to Massachusetts flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Massachusetts.

The cheapest ticket to Massachusetts from Chicago found in the last 72 hours was to Boston, at $97 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 72 hours was $97.

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

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $582, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Massachusetts, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Massachusetts is September, when tickets cost $191 (return) on average. On the other hand, the most expensive months are April and May, when the average cost of round-trip tickets is $293 and $266 respectively.

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

The average price of all round-trip flights from Chicago to Massachusetts clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago to Massachusetts, look for departures on Wednesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Massachusetts, Wednesday 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 calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Massachusetts, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Massachusetts, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.


Good to know

Low seasonFebruary
High seasonOctober
Cheapest flight$53
Best time to beat the crowds with an average 0% drop in price.
Most popular time to fly and prices are also 7% 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 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.

  • 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 $194 on average. Morning departures are around 12% 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 $300.

Top 5 airlines serving from Chicago to Massachusetts

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Massachusetts. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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
DeltaOverall score based on 7934 reviews
7.3Food
8.2Boarding
8.5Crew
7.9Entertainment
7.9Comfort
Airline reviews

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

8.0 ExcellentFredrick, Apr 2025GSO - DTW
Read more Delta reviews

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

Delta is a cut above the others in customer service.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

Great flight. Departed early, arrived early. However they were out of meals for sale. Also, we arrived early and the gate was not available so we sat on the taxiway for quite a while (not JetBlue’s fault).

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

It was too hot in the cabin. The AC did not help.

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Loved the leg room and tvs screens on the seats and free WiFi. Wish the price was lower and could save by rebooking

It took 1-1/2 hours to get our luggage after we landed. That to me is unacceptable

The flight was delayed for 4 hours. Once onboard the crew was wonderful.

Overall was excellent. Will definitely us JetBlue in the future.

Love the mosaic program, being able to move to an extra space seat for free is awesome

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

Good crew and safe. However, comfort and being nickeled-and-dimed are my issues. $75 each way for luggage is exhortation. The space to the next seat is so close you cannot open a laptop. The magazine rack doesn’t hold your items. Not a fan.

We had a 5 hour delay, which resulted in my arriving at my final destination at 2 am instead of 9 pm

WiFi could have been a little more consistent - otherwise a phenomenal and positive experience. The 1000 mile giveaway was awesome!!!

The flight took an extra 30 min to take off because we were waiting for crew to board then it took another 30 min to get off the plane because there was no parking. Just overall ridiculous also please add a head rest my neck was gonna snap off thanks.

Loved staff help @ kiosk, staff on airplane. Commitment to punctuality. I sat in a "blocked" row, where the middle seat had no passenger & loved it! I appreciate not having to pay for water, which I've experienced even on international flights. Only negative was how dirty the bathroom was for a 4.5 hrs flight. But I don't think flight attendants monitor this.

Your employees need to learn how to talk to people as creations of Yah. We are not their children nor are we lower than them.

Helpful attendants at check-in is very good. The $70 charge for a checked bags I didn't care for.and the constant charges for picking a seat and faster check-in are too much. Please cut the prices by at least 50% would be fantastic!

Everything you need to know for your flight from Chicago to Massachusetts

Cabin class types available on flights to Massachusetts

Cabin classes available on flights to Massachusetts. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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