$49 Find Cheap Flights from Illinois to Massachusetts

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Low season

January

High season

July

Cheapest flight

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Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 2% increase in price.
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 airlines fly most frequently to Massachusetts?

    Illinois and Massachusetts are connected by different airlines. The airlines that fly that route the most regularly are American Airlines (67 flights per week), Qatar Airways (58 flights per week), and United Airlines (52 flights per week).

  • How many airports are there in Massachusetts?

    There are 6 airports in Massachusetts. The busiest airport is Boston Logan Airport (BOS), with 98% of all flights arriving there.

  • 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 $152.

  • 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 $250. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $329 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 $196 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.

  • What is the cheapest flight to Massachusetts?

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

  • 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 June, when the average cost of round-trip tickets is $323 and $322 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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

  • How many cities have direct flights to Massachusetts?

    From Illinois, there are direct flights to Massachusetts from 1 city. This city is Chicago and there are 632 direct flights each week.

  • How many direct flights to Massachusetts are there each day?

    There are around 91 direct flights from within Illinois to Massachusetts every day. Most flights (47%) depart in the morning.

  • How many direct flights to Massachusetts are there each week?

    Each week there are around 632 direct flights from within Illinois to Massachusetts. The most common day for departures is Sunday, with 18% of flights taking off on this day.

  • How long is the flight to Massachusetts?

    An average nonstop flight from Illinois to Massachusetts takes 5h 51m, covering a distance of 888 miles. The shortest route is Chicago Midway Airport (MDW) to Albany (ALB) with an average flight time of 1h 55m.

  • How many long-haul flights are there to Massachusetts each week?

    There are not any long-haul (6-12 hour flight duration) or medium-haul (3-6 hour flight duration) flights to Massachusetts. Instead, there are 632 short-haul flights (up to 3 hour flight duration), with the most arriving from Chicago.

  • What are the most popular destinations in Massachusetts?

    Based on KAYAK flight searches, the most popular destination is Boston (73% of total searches to Massachusetts). The next most popular destinations are Hartford (14%) and Albany (11%). Searches for flights to Nantucket (1%), to West Tisbury (1%) and to Worcester (0%) are also popular.

See more FAQs

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 7899 reviews
7.3Food
7.9Entertainment
8.2Boarding
8.0Comfort
8.5Crew
Airline reviews

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

10.0 ExcellentSunderesh, Mar 2025AUS - BOS
Read more Delta reviews

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.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Terrible and im avoiding them in the future. My initial flight was delayed causing me to rebook my flight and when speaking with the representative to rebook I explained this is the second time my flights were delayed and they did nothing to help me. I wasn't booked to comfort plus or given a voucher or anything. I was almost late for my meeting that I needed to attend on Monday because of the games delta played delaying my flights even more and putting me in the very back of the plane next to an extremely intoxicated passenger

Flights on time. .Ride was as comfortable as can be expected in steerage. Luggage arrived at destination. Attendants were fairly friendly.

Great staff. Wifi is terrible. Signing up for skylines is a painstaking process. Had to call customer service just to get my flight itinerary and confirmation sent to me. Consistent delays. A well staffed company that is run so poorly. Upper management needs to be renewed.

The WiFi didn't seem as fast as it normally is

Thank you for not flipping the plane on the run way. You guys get a 5 star rating for the flight!!!

The crew was wonderful and attentive. The seats near exit row were restrictive. Offer healthy snacks please

Delta is a premier airline so my expectations are most always met.

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

Plenty of room for me and the cat in Premium Economy. Seat was comfortable. Boarding was a breeze. The lady at the special check-in desk was great, super helpful and professional.

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

It’s been awhile since I have traveled on United. I, along with my family who were on the flight noted how smoothly everything went . Boarding, flight crew and service was excellent.

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.

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

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 rate it is good we had a 4-hour travel delay at one point but JetBlue gave out food vouchers and travel points credits for another flight so they try to make up for it

Smooth boarding and friendly crew. Unfortunately as soon as we boarded the unit that provides air circulation failed. The pilot informed us and requested maintenance technicians to check it out. The plane became uncomfortably warm without any fresh air coming in. Plus the repair delayed our departure. I am glad the maintenance crew were able to fix the problem. I also was without use of my tv monitor for the first 1/3rd of the trip.

Communication with the customer and stay is important. Staff off with a minor inconvenience but it worked out of course. Also this was a very old Mint Class plane. They snuck this one in on us. The updated aircraft are much better.

The flight itself was fine, but the boarding process was extremely frustrating. There is no one scanning boarding passes - passengers just scan themselves and enter the jetway. By the time my husband and I got on the plane and were halfway to our seats they determined there were too many bags on the plane and everything at that point needed to be checked. This created a lot of unnecessary chaos. They should have alerted people before getting on the plane that they would need to start checking bags instead of waiting until people were already on the plane.

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.

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.

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!

Absolutely the MOST uncomfortable seat I've EVER had on ANY airline. It should be a criminal act (cruel & unusual punishment). NEVER AGAIN will I travel your airline.

The flight was delayed over an hour and we had to sit on the plane. Crew does not apologize due to the delay. Spirit will NEVER do anything to give a customer a better experience. A child next to me was kicking me the whole time. I don't ever enjoy flying with Spirit.

Easy! As long as you don’t mind no frills, our flight was enjoyable and on time

Book cheap flights from Illinois to Massachusetts

Recent round-trip flight deals

5/14Wed
nonstopJetBlue
2h 28mORD-BOS
5/14Wed
nonstopJetBlue
3h 06mBOS-ORD
$92
5/7Wed
nonstopUnited Airlines
2h 28mORD-BOS
5/8Thu
nonstopUnited Airlines
2h 57mBOS-ORD
$97
4/12Sat
nonstopSouthwest
2h 20mMDW-BOS
4/14Mon
nonstopSouthwest
2h 35mBOS-MDW
$97
5/3Sat
nonstopAmerican Airlines
2h 28mORD-BOS
5/6Tue
nonstopAmerican Airlines
2h 58mBOS-ORD
$98
4/12Sat
nonstopAmerican Airlines
2h 30mORD-BOS
4/14Mon
nonstopAmerican Airlines
3h 08mBOS-ORD
$99
4/30Wed
1 stopSpirit Airlines
13h 35mORD-BOS
5/7Wed
1 stopSpirit Airlines
8h 15mBOS-ORD
$105
4/12Sat
nonstopSouthwest
2h 20mMDW-BOS
4/14Mon
1 stopSouthwest
6h 35mBOS-MDW
$107
5/14Wed
1 stopSpirit Airlines
13h 03mORD-BOS
5/21Wed
1 stopSpirit Airlines
8h 15mBOS-ORD
$118
5/20Tue
nonstopDelta
2h 25mORD-BOS
5/24Sat
nonstopDelta
3h 04mBOS-ORD
$147
9/17Wed
nonstopDelta
2h 30mORD-BOS
9/17Wed
nonstopDelta
2h 52mBOS-ORD
$166

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Recent one-way flight deals

9/26Fri
nonstopUnited Airlines
2h 30mORD-BOS
$49
4/19Sat
nonstopSouthwest
2h 15mMDW-BOS
$49
9/17Wed
nonstopAmerican Airlines
2h 44mORD-BOS
$50
4/11Fri
nonstopJetBlue
2h 29mORD-BOS
$59
5/14Wed
1 stopSpirit Airlines
8h 39mORD-BOS
$60
5/7Wed
1 stopSpirit Airlines
8h 39mORD-BOS
$61
4/23Wed
nonstopDelta
2h 26mORD-BOS
$69
6/4Wed
nonstopAmerican Airlines
2h 35mORD-BOS
$77
5/11Sun
nonstopDelta
2h 25mORD-BOS
$79
4/19Sat
nonstopJetBlue
2h 29mORD-BOS
$89

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Last minute flights from Illinois to Massachusetts

Last minute flight, train and bus deals

4/5Sat
multi-stopSpirit Airlines
13h 38mORD-BOS
4/10Thu
multi-stopSpirit Airlines
13h 05mBOS-ORD
$166
4/5Sat
multi-stopSpirit Airlines
13h 38mORD-BOS
4/10Thu
multi-stopSpirit Airlines
13h 05mBOS-ORD
$170
4/6Sun
nonstopUnited Airlines
2h 28mORD-BOS
4/10Thu
nonstopUnited Airlines
2h 57mBOS-ORD
$213
4/4Fri
nonstopJetBlue
2h 29mORD-BOS
4/9Wed
nonstopJetBlue
3h 12mBOS-ORD
$223
4/4Fri
nonstopUnited Airlines
2h 28mORD-BOS
4/8Tue
nonstopUnited Airlines
2h 57mBOS-ORD
$233
4/4Fri
multi-stopAmerican Airlines
4h 00mORD-BOS
4/8Tue
nonstopAmerican Airlines
2h 56mBOS-ORD
$245
4/2Wed
nonstopAmerican Airlines
2h 16mORD-BOS
4/8Tue
nonstopAmerican Airlines
3h 10mBOS-ORD
$258
4/5Sat
nonstopJetBlue
2h 28mORD-BOS
4/9Wed
nonstopJetBlue
3h 12mBOS-ORD
$264
4/3Thu
multi-stopDelta
6h 15mORD-BOS
4/8Tue
nonstopDelta
3h 02mBOS-ORD
$273
4/4Fri
nonstopDelta
2h 28mORD-BOS
4/7Mon
nonstopDelta
2h 56mBOS-ORD
$313

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Everything you need to know for your flight to Massachusetts

Cabin class types available on flights to Illinois

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