$52 Find Cheap Flights from Illinois 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 Illinois to Massachusetts departing on 1/14. 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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Good to know

Low season

January

High season

July

Cheapest flight

$52
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly and prices are also 25% lower on average.
Flight from Chicago Midway 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 to Massachusetts from 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 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 to Massachusetts with an airline and back to Illinois 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 to Massachusetts from Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 4 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.
8.9
Cape AirOverall score based on 39 reviews
8.5Comfort
8.9Entertainment
8.6Boarding
9.2Crew
8.6Food
Airline reviews

It’s less complicated from Culebra to SJU airport. Next time I will prefer to leave from Isla Grande airport to Culebra !!

10.0 ExcellentSonia, Apr 2023CPX - SJU
Read more Cape Air reviews

It’s less complicated from Culebra to SJU airport. Next time I will prefer to leave from Isla Grande airport to Culebra !!

10 seat Cesna. Equal parts transportation and adventure. 20 minute hop at 10000 feet and 160 mph, sitting 10 feet from the pilot. Panoramic views of the island. Very simple boarding, very low stress. VQS airport tiny, undeveloped. Highly recommended flight, Cape Air doing a great job here.

We traveled in a small Cesna so there was no food or entertainment. The pilot was excellent enjoy being able to see the places we were flying above. It was an OK flight.

Very smooth flight and landing. Pilot delivered his safety instruction in such a monotone that it wasn’t easily understandable. Words were said but he didn't communicate to us. If he was communicating to someone he cared about, he would have used inflection and other nuances of speaking. Virtually all emphasis was removed so it was just blah blah blah (really fast, like the end of a Pharma commercial)

My pilot on Cape Air was AMAZING!!!! I hoping that next time I fly I have him as my pilot. He made me feel safe and secure in his skills.

I so appreciate this service into and out of Glendive. Always a good experience with crew and support team.

It was not what I had expected but it was a great way to see the landscape.

Pros: "ground crew, pilot, flight was smooth and gate connections to Jet Blue in Boston were fantastic!"
Cons: "leg room"
Pros: "The pilot was kind and to the point."
Cons: "The guy who boarded us told me to wait as his computer could not check me in. 10min later he is rushing me to get on the runway. It was 30min before scheduled take off. I had ordered food and had to cancel my order before the café had finished, so he wasted food and did not get paid and I was hurried and boarded the plane hungry. I probably won't use Cape Air again unless it's an emergency situation"
Cons: "Boarded half hour late. No explanation. Pretty standard on Cape Air these days"

Everything was good except food , food choices was very less. Washrooms were closed.overall good experience.

On time boarding I would like to see ground hostess to help transit customers to direct them to the right terminal and boarding gate. Last night, all the transit customers on SQ484 arriving Singapore had to merry go round to look for terminal and boarding gate to board SQ128 transit to KL Malaysia. We went to Terminal 3 taking the Skytrain to T3 and back to T3 to get out to look for different Skytrain to T2. On arrival t2, we had to go round to ask which boarding gate to KL. We only had 5 minutes to make to the boarding time at 6:55pm but we already spent more than 30 minutes running around to find the boarding gate. We were late at the boarding gate.

The seats were more narrow than at other lines. Food was mediocre (economy class)

This flight was 16 hours and they made it very tolerable. Seats were comfortable and the staff very accommodating. I had plenty of inflight entertainment. Food was very good.

The crew and their service was top notch, but the plane itself seemed to be on the older side and worn out. Also, the food could’ve been better. 9 out of 10.

Service excellent would chose Singapore airlines as my first choice

The staff were amazing and very kind. The seats recline a little too far back and are up close when sitting behind.

My groups frequent flyer star allianceUnited airline miles was not accepted. The Singapore premium economy bag had to be requested, it was very lacking- no toothbrush. I paid more than double than economy but could only use the bathrooms sharing with economy which was hardly available and had to wait in line. Is the 2X $ worth it just for a larger seat???? It is questionable. Seats were not that comfortable. My husband’s seat had white stains on it- had to wipe it down. Our headphones did not have covers on it. Food- way too much.

The booking experience was bad. Our six character booking ID number disappeared the day before the flight, We could not find out what happened or what was the status of our flight, scheduled for the next day. We finally found the right number to contact Singapore Airlines on the matter (not easy). The Singapore agent worked through the issue in a little over thirty minutes on the phone, the day before the flight. That was great. I'm very happy with Singapore Airlines and their performance. Contact with a competent person on the matter was near impossible. It seems no one in business these days wants to deal with customers once they've pocketed the money. There were resellers, including Kayak, involved in the chain. When we finally got through to Underpricer, we did get a return call that could have proved helpful. But by that time the matter had been resolved by the Singapore agent. Majestic Vacations, the reseller who received the payment was less than worthless. That's just a fast buck operation. Ugh.

Excellent- a lot of food Disappointed with the premium economy pouch- did not have toothbrush and tooth paste or socks. Other airlines provide them

Food was hood for airline food with good poftion and variety in meals. Frequency of beverage service was very low and amount of soda with meals was inadequate.

bad… no veg food was provided eventhough i pre ordered special meal

Excellent service provided the flight crew. Food and drinks were very good.

Meal options for vegetarians can be provided… Nothing was offered for me for dinner.. crew just said no vegetarian option available and did even bother to provide any alternatives or something to eat.

Cathay has a great reputation, though it's baseline economy seating is nothing to write home about (and SE Asia flight passengers sometime lack 'routine stateside' etiquette). On the other hand, food was great, flight attendants were nice, and price was very good~

I was really impressed with the experience it was my first trip overseas. Nice staff

Not enough food for everyone. . Always run out of food when we ask

The crews were smiling all the time with soft tunes when they spoke; the food was excellent. Thank you!

They charged me $900 to board my flight I already paid for just because I missed my previous flight. I do not recommend this airline by any means.

Not good. Small seats. Not enough food that customers wanted. No special requests were given that i could see. Slow response from flight attendants

Not a frequent user of their website booking. Booked my check-in baggage and only realized that I did not book my check in baggage for return flight. The receipt was not clear in identifying that as well. Was charged exorbitantly at check in counter. Bad taste for sure when it is a business trip and not leisure trip. Baggage was delayed for more than an hour at belt back in SG.

Boarding took forever. It's also weird that we paid more (for preferred seats) to get on the plane last. Inflight WiFi never worked the entire trip. I want my money back.

The cosmetic condition was pretty run down. The carpets were badly worn out. Even the paint on the wings was chipped and peeled! Looks like they are running these 787s to the ground..

WiFi didn’t work on both sectors so made killing time harder - planes clean modern and good flight crew - would do again if WiFi works

6hrs fly they dont give you a glass of water from seoul to singapore need to buy drink and food plus they charge for bag on international fly is always Free 1 bag from seoul to singapore is Not a local fly you are traveling true asia same story from singapore to Bali no water drink after payment for bag drink cost more the regular airline Well never use this company again we use regular company like Delta korea japan China and even scoot parent company Singapore Air

We had 2 attempts to land at Singapore Changing during a thunderstorm. Everything was delayed by 1 hour plus.

Boarding was not accordingly after front seat, bmf then back seat. This delayed for at least 40mins or more. The staff at Jakarta can do better. Is chaos at the entry to board the plane. This tarnished Scoot reputation when everyone was talking about it.

The crew was not customer oriented at all, even confrontational . The aircraft needs more attention to detail as far as comfort, and the 1 hour sitting at the gate with no air is inexcusable

We flew on the 787 Dreamliner direct to main gate at KLIA2, quick entry via eGate and on the train 41mins after touchdown. Go well SCOOT

Was on scoot plus. The only good thing about the flight was the spacious seats. Tables and armrests were extremely dirty Food: bad Entertainment: non existent Wifi: unable to connect, then was painfully slow that we couldn’t even send messages Good thing we had a night flight, so we just slept throughout.

Book cheap flights from Illinois to Massachusetts

Recent round-trip flight deals

12/10Tue
1 stopSpirit Airlines
13h 40mORD-BOS
12/11Wed
1 stopSpirit Airlines
12h 06mBOS-ORD
$101
12/11Wed
1 stopFrontier
10h 33mMDW-BOS
12/18Wed
1 stopFrontier
8h 39mBOS-MDW
$103
1/13Mon
1 stop
6h 37mORD-BOS
1/14Tue
1 stop
9h 42mBOS-ORD
$120
1/8Wed
1 stop
10h 41mORD-BOS
1/10Fri
1 stop
10h 29mBOS-ORD
$123
12/10Tue
nonstopJetBlue
2h 22mORD-BOS
12/15Sun
nonstopJetBlue
3h 06mBOS-ORD
$157
12/13Fri
nonstopSouthwest
2h 10mMDW-BOS
12/15Sun
nonstopSouthwest
2h 45mBOS-MDW
$158
12/10Tue
1 stopJetBlue
4h 29mORD-BOS
12/14Sat
nonstopJetBlue
3h 06mBOS-ORD
$166
12/6Fri
nonstopUnited Airlines
2h 25mORD-BOS
12/8Sun
1 stopUnited Airlines
4h 49mBOS-ORD
$167
12/13Fri
nonstopSouthwest
2h 10mMDW-BOS
1/4Sat
nonstopSouthwest
2h 45mBOS-MDW
$179
12/25Wed
nonstopUnited Airlines
2h 27mORD-BOS
12/28Sat
nonstopUnited Airlines
3h 03mBOS-ORD
$218

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Recent one-way flight deals

1/14Tue
1 stopFrontier
6h 06mMDW-BOS
$52
12/17Tue
1 stopFrontier
5h 57mORD-BOS
$53
12/6Fri
1 stopSpirit Airlines
11h 53mORD-BOS
$69
12/6Fri
1 stopSpirit Airlines
11h 53mORD-BOS
$71
2/3Mon
nonstopDelta
2h 35mORD-BOS
$79
2/14Fri
1 stopUnited Airlines
5h 05mORD-BOS
$88
12/24Tue
nonstopDelta
2h 28mORD-BOS
$95
2/17Mon
1 stopJetBlue
5h 38mORD-BOS
$98
12/25Wed
nonstopJetBlue
2h 29mORD-BOS
$99
12/8Sun
1 stopUnited Airlines
5h 06mORD-BOS
$113

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Last minute flights from Illinois to Massachusetts

Last minute flight, train and bus deals

11/26Tue
multi-stop
19h 51mORD-BOS
11/29Fri
nonstop
3h 07mBOS-ORD
$159
11/26Tue
multi-stop
6h 38mORD-BOS
12/9Mon
multi-stop
7h 49mBOS-ORD
$187
11/24Sun
nonstopSpirit Airlines
2h 19mORD-BOS
11/29Fri
nonstopSpirit Airlines
3h 07mBOS-ORD
$196
11/25Mon
nonstopSpirit Airlines
2h 19mORD-BOS
12/3Tue
nonstopSpirit Airlines
3h 11mBOS-ORD
$200
11/26Tue
multi-stopFrontier
4h 43mMDW-BOS
12/10Tue
multi-stopFrontier
6h 42mBOS-MDW
$208
11/26Tue
multi-stopFrontier
4h 43mMDW-BOS
12/6Fri
multi-stopFrontier
9h 24mBOS-MDW
$218
11/26Tue
nonstopJetBlue
2h 13mORD-BOS
11/27Wed
nonstopJetBlue
2h 47mBOS-ORD
$312
11/25Mon
multi-stopJetBlue
7h 39mORD-BOS
11/27Wed
nonstopJetBlue
2h 47mBOS-ORD
$321
11/24Sun
multi-stopUnited Airlines
7h 17mSTL-BOS
12/4Wed
multi-stopUnited Airlines
5h 31mBOS-STL
$610
11/25Mon
multi-stopUnited Airlines
7h 04mMLI-BDL
12/3Tue
multi-stopUnited Airlines
5h 22mBDL-MLI
$624

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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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