$55 Find Cheap Flights from Illinois to Massachusetts

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Good to know

Low seasonJanuary
High seasonOctober
Cheapest flight$55
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from Chicago O'Hare Airport to Boston

FAQs for booking flights from Illinois to Massachusetts

  • How does KAYAK find such low prices on flights from Illinois 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 Illinois to Massachusetts.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Illinois to Massachusetts?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Illinois 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 Illinois 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 Illinois 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 Illinois 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 Illinois to Massachusetts up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which is the cheapest airport to fly into in Massachusetts?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Massachusetts is Boston Logan Intl Airport (BOS), with an average flight price of $187.

  • What is the cheapest day to fly to Massachusetts?

    Based on KAYAK data, the cheapest day to fly to Massachusetts is Wednesday where round-trip tickets can be as cheap as $234. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $304 on average.

  • 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 $193 on average. Morning departures are around 15% 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 $290.

  • What is the cheapest flight to Massachusetts?

    The cheapest ticket to Massachusetts from Illinois found in the last 72 hours was to Boston, at $104 round-trip. The most popular route is Chicago Midway Airport (MDW) to Boston (BOS) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $104.

  • What is the cheapest month to fly from Illinois to Massachusetts?

    The cheapest month for flights from Illinois to Massachusetts is January, when tickets cost $185 (return) on average. On the other hand, the most expensive months are February and October, when the average cost of round-trip tickets is $323 and $313 respectively.

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

    To get a below average price on the flight from Illinois to Massachusetts, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

  • How long is the flight to Massachusetts?

    An average nonstop flight from Illinois to Massachusetts takes 6h 11m, covering a distance of 888 miles. The shortest route is Chicago Midway Airport (MDW) to Albany (ALB) with an average flight time of 1h 50m.

  • What are the most popular destinations in Massachusetts?

    Based on KAYAK flight searches, the most popular destination is Boston (80% of total searches to Massachusetts). The next most popular destinations are Hartford (9%) and Albany (7%). Searches for flights to Nantucket (3%), to Worcester (1%) and to West Tisbury (1%) are also popular.

Top 5 airlines serving from Illinois to Massachusetts

 
Need help choosing which airline to fly with from Illinois 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 7950 reviews
8.2Boarding
7.3Food
8.5Crew
7.9Comfort
7.9Entertainment
Airline reviews

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

10.0 ExcellentHartaj, Jun 2025EWR - RDU
Read more Delta reviews

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

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

Communication since no reason or explanation was given for 3 hrs delay

Flight was delayed several 3 hours - no reason was given and no communication what so ever.

No overhead baggage room even though I was seated in row 2. Consequently had to check in my carry on bag. Baggage carousel was jammed. Took 45 min to get my bag.

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

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.

I had a horrible experience from the time I dropped off my bags until the time I landed. The staff taking the bags at the check-in counter prior to security, forced me to check my baby stroller, even though it weighed less than 20 pounds. their excuse was that the wheels were too big. I have never had an issue gate checking this exact same stroller in the past either on American or on any other airline. when I asked for the agent to show me the rule about the size of the wheels on strollers, they told me to look it up on the AA website. I did so, and did not find any indication that wheel size was a problem for gate checking strollers. The only limitation would be the weight of the stroller which mine was below. I was left with a one-year-old child and all of my carry-on luggage, diaper bag, and the like to walk around the airport without the assistance of a stroller and had the same issue when I exited the plane and had to go all the way to baggage claim without a stroller. In addition, while on the airplane, I was told I can only get one bag of cookies as a snack, even though I was with a child. Apparently my child and I were supposed to share a cookie. While this latter issue is a minor one, it is just another example of the absolutely horrible customer service that American Airlines provides. In addition, the 737 aircraft that I was on was extremely hot and the air vents above the seat were so far away from the aisle and middle seats that it was comical. I could barely reach the air vent to adjust it. I had to ask the person in the window seat to do it for me. The whole experience was just a nightmare.

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

Flight was late and TSA had shut down so (almost) no passengers could get to the gate. American failed to inform TSA to stay open! Needed to get back home so we had to rent a car & drive 13 hours all through the night. It was bad.

The flight was on time and everything went very smoothly.

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.

Need screens for tv/movies. Seats are more cramped than any other airlines. Seats are hard. They don’t recline. And in flight time should not be used for sales pitches.

Boarding east and ontime. Seat spacing was tight, and seats don’t recline.

The flight, the pilot, the flight crew, and the ground personnel were all great, despite the sudden and lengthy FAA Ground Stop in Boston, which SPIRIT obviously had nothing to do with and no control over.

Not great. Overpriced and charge you for everything. All but breathing was an extra charge. Never again! Oh if you didn’t check a carry on, you couldn’t use the overhead bins. Crew said those spaces were not available. Personal items MUST go on floor. Yet, there was only 50% capacity at best! So ridiculous.

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.

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.

Book cheap flights from Illinois to Massachusetts

Recent round-trip flight deals

7/1Tue
1 stopSpirit Airlines
9h 32mORD-BOS
7/2Wed
1 stopSpirit Airlines
13h 59mBOS-ORD
$112
7/8Tue
1 stopSpirit Airlines
9h 32mORD-BOS
7/9Wed
1 stopSpirit Airlines
13h 16mBOS-ORD
$114
8/9Sat
nonstopAmerican Airlines
2h 28mORD-BOS
8/12Tue
nonstopAmerican Airlines
2h 57mBOS-ORD
$125
8/19Tue
nonstopAmerican Airlines
2h 34mORD-BOS
8/23Sat
nonstopAmerican Airlines
2h 55mBOS-ORD
$126
9/26Fri
nonstopJetBlue
2h 33mORD-BOS
9/28Sun
nonstopJetBlue
2h 57mBOS-ORD
$131
7/10Thu
nonstopUnited Airlines
2h 27mORD-BOS
7/14Mon
nonstopUnited Airlines
2h 52mBOS-ORD
$137
8/22Fri
nonstopUnited Airlines
2h 30mORD-BOS
8/24Sun
nonstopUnited Airlines
2h 56mBOS-ORD
$149
9/27Sat
nonstopDelta
2h 30mORD-BOS
9/27Sat
nonstopDelta
2h 55mBOS-ORD
$153
7/16Wed
nonstopDelta
2h 31mORD-BOS
7/29Tue
nonstopDelta
2h 58mBOS-ORD
$155
7/16Wed
nonstopJetBlue
2h 24mORD-BOS
7/21Mon
nonstopJetBlue
2h 55mBOS-ORD
$177

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Recent one-way flight deals

7/9Wed
1 stopSpirit Airlines
12h 03mORD-BOS
$55
7/8Tue
1 stopSpirit Airlines
9h 32mORD-BOS
$56
8/25Mon
nonstopAmerican Airlines
2h 28mORD-BOS
$62
8/5Tue
nonstopUnited Airlines
2h 38mORD-BOS
$63
8/26Tue
nonstopAmerican Airlines
2h 32mORD-BOS
$64
6/20Fri
nonstopJetBlue
2h 24mORD-BOS
$69
10/9Thu
nonstopUnited Airlines
2h 32mORD-BOS
$87
6/18Wed
nonstopDelta
2h 31mORD-BOS
$89
7/29Tue
1 stopDelta
5h 21mORD-BDL
$99
7/25Fri
1 stopJetBlue
4h 37mORD-ACK
$113

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Last minute flights from Illinois to Massachusetts

Last minute flight, train and bus deals

6/17Tue
nonstopJetBlue
2h 24mORD-BOS
6/18Wed
nonstopJetBlue
2h 55mBOS-ORD
$137
6/17Tue
nonstopSouthwest
2h 10mMDW-BOS
6/17Tue
nonstopSouthwest
2h 50mBOS-MDW
$137
6/17Tue
nonstopDelta
2h 31mORD-BOS
6/17Tue
nonstopDelta
3h 00mBOS-ORD
$157
6/17Tue
nonstopUnited Airlines
2h 30mORD-BOS
6/24Tue
multi-stopUnited Airlines
4h 55mBOS-ORD
$185
6/17Tue
nonstopDelta
2h 31mORD-BOS
6/20Fri
nonstopDelta
3h 00mBOS-ORD
$207
6/17Tue
nonstopAmerican Airlines
2h 23mORD-BOS
6/21Sat
nonstopAmerican Airlines
3h 00mBOS-ORD
$223
6/17Tue
nonstopAmerican Airlines
2h 40mORD-BOS
6/21Sat
multi-stopAmerican Airlines
6h 25mBOS-ORD
$233
6/17Tue
multi-stopSpirit Airlines
12h 01mORD-BOS
6/24Tue
multi-stopSpirit Airlines
13h 59mBOS-ORD
$245
6/16Mon
multi-stopSpirit Airlines
5h 05mORD-BOS
6/26Thu
multi-stopSpirit Airlines
13h 59mBOS-ORD
$256
6/17Tue
multi-stopUnited Airlines
6h 41mORD-BOS
6/20Fri
multi-stopUnited Airlines
7h 47mBOS-ORD
$307

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Everything you need to know for your flight to Massachusetts

Cabin class types available on flights to Illinois

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

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