$68 Find Cheap Flights from Illinois to Massachusetts

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Low seasonJanuary
Cheapest flight$68
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 9% 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?

    Air New Zealand connects Illinois to Massachusetts with 79 flights per week. American Airlines also offers 79 flights per week, while United Airlines follows with 72 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 97% 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 $208.

  • 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 $230. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $291 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 $209 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 afternoon, which is peak travel time and where the average cost of a ticket is $288.

  • What is the cheapest flight to Massachusetts?

    The cheapest ticket to Massachusetts from Illinois found in the last 72 hours was to Boston, at $106 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 $106.

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

    The cheapest month for flights from Illinois to Massachusetts is July, when tickets cost $247 (return) on average. On the other hand, the most expensive months are January and April, when the average cost of round-trip tickets is $414 and $332 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, which saves you about 38% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 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 597 direct flights each week.

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

    There are around 86 direct flights from within Illinois to Massachusetts every day. Most flights (49%) depart in the morning.

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

    Each week there are around 597 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 6h 32m, 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.

  • 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 597 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 (63% of total searches to Massachusetts). The next most popular destinations are Hartford (21%) and Albany (13%). Searches for flights to Nantucket (1%), to West Tisbury (1%) and to Worcester (1%) are also popular.

Reviews of the 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
SouthwestOverall score based on 4333 reviews
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
7.0Food
Airline reviews

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

2.0 MediocreStuart, Mar 2026
HOU - STL
Read more Southwest reviews

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

I liked it better when you were truer to your roots Am paying more for less fun

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

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.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

The flight was delayed 90 minutes The Gate was wrong The Restroom on Aircraft was not clean There was a half used water bottle in my seat

Delta is always a wonderful experience. A clean plane and the crew is really friendly.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

Got to fly my favorite plane, the Boeing 767-400ER, to Milan. The soft blush pink mood lighting during meal service was very beautiful and gorgeous. The service was top-notch, and our flights were on time. I highly recommend Delta.

I am still at the Airport! Delayed Delayed and Delyaed

I took seat 15A in anticipation of window seat, there is no window.

The first class flight attendant was awful to everyone. Very rude; no customer service. She should not be working in first class.

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

Awful. No counter attendants. No dinner offered due to delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

I like flying first class, and United has a nice one

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

For the price point it was very good. Definitely leave on the earlier flights as it can become terribly crowded later in the day

Absolutely horrible. Flight was delayed 4 hours and they had no clue what was going on.

Onboard functioning wide-variety entertainment on a budget and having an open pantry is nice. Seats are not comfortable but go provide plenty of legroom for a 6'2" 260lbs man.

Even though the weather made a lot of flights become cancelled Jet Blue made the flight that was supposed to leave at 9 pm and we left at 12:15 am and I was so grateful- Thanks to the Senior Jet Blue Staff who made those decisions

Worst customer service ever experienced on the planet, dirty plane, no communication, and severe delays

Flight cancelled 2 hours prior to boarding. No explanation. No refunds.

Delayed by 1.5 hours. Terrible apologies, half hearted at best. It will be a LONG time until i book w Jet Blue again. Very disappointed.

My check in was stressful. I somehow lost my seat from my original booking, the plane showed no availability/no seat when it was time to check-in. I called and was instructed to try to get a seat at the airport. I asked if it was a full flight and the travel agent said the site showed some seating but was not able to secure one for me. Why not? On my way to the airport the app finally revealed one available seat towards the back of the aircraft that I was able to book. It ended up being an overbooked flight, so glad I wasn't stuck.

Flights with JetBlue from San Diego to Boston are a miserable experience. The flight was delayed about 1.5 hours due to “weather” supposedly but the flights for other airlines left on time so it just have been some kind of weather that only affects JetBlue. I had a small carry on - purse. The crew stored it in a bin 2 rows down from me because they were using the bin next to my seat for other people’s stuff. The TV screen in the emergency row seats does not work. It just was awful from start to finish. When we landed, we had to sit inside the plane for a very long time because the plane had to be moved to a different gate.

They made me check my bag and I didn't need to as there was overhead space available. I paid for a seat towards the front of the plane and it didn't recline. I requested a refund and they declined to give me one.

I was in last row so that is never great bc the person in front of me leaned his seat all the way back into me.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

Half of the TSA checkpoints at PHL are closed. Also, there is no standby for first class passengers. You can only standby for coach. Very dated policy and inconsistent with peers.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

We had a male flight attendant who was super attentive and wonderful! Very professional. I have both gluten and dairy intolerance, and was only able to get a gluten free part, and not the dairy free part of the meal. Easy to order ahead of time and I appreciate being able to do that.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

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.