$94 Find Cheap Flights from Massachusetts to Illinois - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Massachusetts to Illinois departing on 8/18. 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
1 adult, Economy, 0 bags

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Good to know

Low seasonJanuary
Cheapest flight$94
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Worcester to Chicago

FAQs for booking flights from Massachusetts to Illinois

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

    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 Massachusetts to Illinois.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Massachusetts to Illinois 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 Massachusetts to Illinois?

    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 Massachusetts to Illinois 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 Massachusetts to Illinois?

    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 Massachusetts to Illinois 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 Illinois?

    Massachusetts and Illinois are connected by different airlines. The airlines that fly that route the most regularly are United Airlines (110 flights per week), Air New Zealand (94 flights per week), and American Airlines (79 flights per week).

  • How many airports are there in Illinois?

    There are 12 airports in Illinois. The busiest airport is Chicago O'Hare Airport (ORD), with 93% of all flights arriving there.

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

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Illinois is Chicago O'Hare Intl Airport (ORD), with an average flight price of $196.

  • What is the cheapest day to fly to Illinois?

    Based on KAYAK data, the cheapest day to fly to Illinois is Friday where round-trip tickets can be as cheap as $318. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $409 on average.

  • What is the cheapest time of day to fly to Illinois?

    The cheapest time of day to fly to Illinois is generally at night, when round-trip flights cost $270 on average. Morning departures are around 3% more expensive than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $372.

  • What is the cheapest flight to Illinois?

    The cheapest ticket to Illinois from Massachusetts found in the last 5 days was to Chicago O'Hare Intl Airport, at $159 round-trip. The most popular route is Nantucket (ACK) to Chicago O'Hare Intl Airport (ORD) and the cheapest round-trip airline ticket found on this route in the last 5 days was $159.

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

    The cheapest month for flights from Massachusetts to Illinois is September, when tickets cost $94 (return) on average. On the other hand, the most expensive months are July and August, when the average cost of round-trip tickets is $200 and $197 respectively.

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

    To get a below average price on the flight from Massachusetts to Illinois, you should book around 2 weeks before departure, which saves you about 23% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

  • How many cities have direct flights to Illinois?

    From Massachusetts, there are direct flights to Illinois from 4 cities. The city with the most direct flights is Boston, with 687 direct flights each week.

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

    There are around 100 direct flights from within Massachusetts to Illinois every day. Most flights (45%) depart in the morning.

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

    Each week there are around 696 direct flights from within Massachusetts to Illinois. The most common day for departures is Sunday, with 17% of flights taking off on this day.

  • How long is the flight to Illinois?

    An average nonstop flight from Massachusetts to Illinois takes 7h 08m, covering a distance of 893 miles. The shortest route is Albany (ALB) to Chicago Midway Airport (MDW) with an average flight time of 2h 05m.

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

    There are not any long-haul (6-12 hour flight duration) or medium-haul (3-6 hour flight duration) flights to Illinois. Instead, there are 696 short-haul flights (up to 3 hour flight duration), with the most arriving from Boston.

  • What are the most popular destinations in Illinois?

    Based on KAYAK flight searches, the most popular destination is Chicago (91% of total searches to Illinois). The next most popular destinations are St. Louis (7%) and Moline (1%). Searches for flights to Evansville (0%), to Peoria (0%) and to Springfield (0%) are also popular.

Reviews of the top 5 airlines serving from Massachusetts to Illinois

 
Need help choosing which airline to fly with from Massachusetts to Illinois? 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.
7.9
SouthwestOverall score based on 4246 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

WiFi was not working and didn’t have a beverage service

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

The seats were comfortable, and the boarding process was pretty smooth.

It was as good as it could be. Flying is not a pleasant experience these days.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

Got on the plane and sat there for an hour before departure.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

Cramped seating for me. Luckily it wasn’t a long flight

5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

The captain was amazing and kept us informed throughout that there would be some rough air. The flight also got delayed but we were able to actually leave on time, which was great.

The staff did not do a good job of getting everyone boarded quickly, so we missed our take off window and had to sit on the tarmac for 20+ min waiting for our turn. The plan was old. Pockets on the back of seats were torn and tearing off. One of the attendants was rude-she would ask a question but he walking away before you finished answering so she kept getting our drink orders wrong.

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

Flight was delayed…once landed at ORD, no gates were available so made us wait for 56 minutes after we landed to let us out of the aircraft!

The flight de-boarded after being informed of a 3 hour delay. The gate agent said we could go to lounge. The flight ended up boarding 20 minutes later and I missed it.

I love the e fact that the staff communicated swiftly when my flight was delayed and gate number changed

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

Despite a bumpy flight the pilot was great. The rest of the crew on the other hand couldn’t care less if a passenger would colapse and die. Horrible service, robot like, lifeless…

Pros: "Im usually not one to sleep on ttransport but I was very comfy on this flight and was able to sleep the whole three hours"
Cons: "The snacks."

Flight left 2 hours late with no explanation as to the delay

Whole experience was poor. Delayed 2 hours. Lied about the delays. Was all jet blues fault and tried to blame on air traffic control. Sent out other let trips and wouldn't allow people to switch aircraft.

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.

The gate attendant in Boston had a high raspy voice and spoke much too fast to be understood. Not pleasant.

It was fine for what it was. It’s not luxury travel but it was efficient, for the most part. Having my carry-on transferred into luggage however, was unwelcome.

We had better-than-average leg room and I loved the access to shows and movies. During boarding, we could not hear the agent even though we were close to the boarding door, which was kind of scary when we realized that half of the passengers had already boarded. Also, the entertainment was awesome, but I could not hear the movie as well as I would have liked, because my headphones were crappy. It would have been better if I could connect my own ear buds via Bluetooth or if JetBlue provided headphones.

I was seated next to an autistic child who was out of control and had a child behind me kicking my seat for most of the trip. I will never fly JetBlue again. Ever. I don't care how cheap it is. It's terrible.

Great price, easy check in, love the free drinks and snacks, and nice crew. The only negative part was waiting for your seat assignment 5 minutes before boarding, and the seats are a bit uncomfortable.

What a great flight. Seats were more comfortable than other airlines. Flight was full but very easy to navigate. No stress no drama

I volunteered to let them put my carry on suitcase in the baggage storage area. But when we landed I was told it was being unloaded IN A DIFFERENT TERMINAL! I had to walk (painful for me) a long way to retrieve my bag and my ride had to move from the waiting area they were in to a totally different one. Not happy.

Everything you need to know for your flight to Illinois

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.