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Cheap flights from Illinois to Massachusetts from $65

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to Massachusetts departing on 5/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Illinois to Massachusetts

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
7:15 pm - 10:49 pm
ORD
-
BOS
2h 34mnonstop
Delta Logo
7:00 am - 8:58 am
BOS
-
ORD
2h 58mnonstop
$126Delta
Fri, May 8 - Thu, Aug 20
Delta Logo
2:10 pm - 5:38 pm
ORD
-
BOS
2h 28mnonstop
Delta Logo
7:15 am - 9:25 am
BOS
-
ORD
3h 10mnonstop
$127Delta
Tue, Mar 31 - Tue, Apr 7
Southwest Logo
5:40 pm - 11:10 pm
MDW
-
BOS
4h 30m
1 stop
Southwest Logo
6:55 pm - 8:45 pm
BOS
-
MDW
2h 50mnonstop
$127Southwest
Fri, May 1 - Mon, May 4
JetBlue Logo
8:30 pm - 11:59 pm
ORD
-
BOS
2h 29mnonstop
JetBlue Logo
6:00 am - 8:00 am
BOS
-
ORD
3h 00mnonstop
$132JetBlue
Fri, Jun 5 - Mon, Jun 8
Southwest Logo
2:10 pm - 11:55 pm
MDW
-
BOS
8h 45m
2 stops
Southwest Logo
6:10 am - 7:55 am
BOS
-
MDW
2h 45mnonstop
$132Southwest
Thu, Apr 9 - Sun, Apr 12
American Airlines Logo
10:24 am - 1:36 pm
ORD
-
ALB
2h 12mnonstop
American Airlines Logo
7:43 pm - 9:40 pm
ALB
-
ORD
2h 57mnonstop
$254American Airlines
Thu, May 14 - Tue, May 19
American Airlines Logo
7:38 pm - 10:57 pm
ORD
-
BDL
2h 19mnonstop
American Airlines Logo
7:29 pm - 9:20 pm
BDL
-
ORD
2h 51mnonstop
$268American Airlines
Fri, Apr 24 - Mon, Apr 27
United Airlines Logo
3:52 pm - 9:56 pm
MLI
-
BOS
5h 04m
1 stop
United Airlines Logo
6:00 am - 12:39 pm
BOS
-
MLI
7h 39m
1 stop
$279United Airlines
Tue, Jun 30 - Sat, Jul 11
JetBlue Logo
6:45 am - 11:51 pm
ORD
-
BDL
16h 06m
1 stop
JetBlue Logo
6:00 am - 11:25 am
BDL
-
ORD
6h 25m
1 stop
$280JetBlue
Tue, Mar 17 - Sat, Mar 21
United Airlines Logo
6:34 pm - 12:59 am
MLI
-
BOS
5h 25m
1 stop
United Airlines Logo
7:19 am - 12:39 pm
BOS
-
MLI
6h 20m
1 stop
$282United Airlines
Fri, Jun 26 - Wed, Jul 1

Delta flights from Illinois to Massachusetts

Our best Delta deals on Illinois to Massachusetts flight tickets
Delta
May 8
ORD7:15 pmChicago O'Hare Intl
2h 34m
BOS10:49 pmBoston Logan Intl
Aug 20
BOS7:00 amBoston Logan Intl
2h 58m
ORD8:58 amChicago O'Hare Intl
$126
Delta
Mar 31
ORD2:10 pmChicago O'Hare Intl
2h 28m
BOS5:38 pmBoston Logan Intl
Apr 7
BOS7:15 amBoston Logan Intl
3h 10m
ORD9:25 amChicago O'Hare Intl
$127
Delta
Apr 30
ORD6:50 amChicago O'Hare Intl
2h 21m
BOS10:11 amBoston Logan Intl
May 3
BOS6:00 amBoston Logan Intl
3h 09m
ORD8:09 amChicago O'Hare Intl
$128

Southwest flights from Illinois to Massachusetts

Our best Southwest deals on Illinois to Massachusetts flight tickets
Southwest
May 1
MDW5:40 pmChicago Midway
4h 30m
1 stop
BOS11:10 pmBoston Logan Intl
May 4
BOS6:55 pmBoston Logan Intl
2h 50m
MDW8:45 pmChicago Midway
$127
Southwest
May 12
MDW7:50 amChicago Midway
8h 25m
2 stops
BOS5:15 pmBoston Logan Intl
May 12
BOS6:20 pmBoston Logan Intl
2h 50m
MDW8:10 pmChicago Midway
$132
Southwest
Apr 30
MDW2:10 pmChicago Midway
8h 00m
1 stop
BOS11:10 pmBoston Logan Intl
May 4
BOS3:45 pmBoston Logan Intl
2h 45m
MDW5:30 pmChicago Midway
$133

momondo Fare Finder

 
Customize your flight search to find flights from Illinois to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated March 3, 2026.
Use the filters below to find and compare flights from Illinois to Massachusetts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 5/8

7:15 pm-10:49 pm

Nonstop2h 34m

Boston Logan Intl

Thu 8/20

7:00 am-8:58 am

Nonstop2h 58m

$126

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 3/31

2:10 pm-5:38 pm

Nonstop2h 28m

Boston Logan Intl

Tue 4/7

7:15 am-9:25 am

Nonstop3h 10m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 5/1

5:40 pm-11:10 pm

1 stop4h 30m

Boston Logan Intl

Mon 5/4

6:55 pm-8:45 pm

Nonstop2h 50m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 6/5

8:30 pm-11:59 pm

Nonstop2h 29m

Boston Logan Intl

Mon 6/8

6:00 am-8:00 am

Nonstop3h 00m

$132

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 4/9

2:10 pm-11:55 pm

2 stops8h 45m

Boston Logan Intl

Sun 4/12

6:10 am-7:55 am

Nonstop2h 45m

$132

ChicagoAlbany

ORD - ALB

ORDALB

Chicago O'Hare Intl

Thu 5/14

10:24 am-1:36 pm

Nonstop2h 12m

Albany Intl

Tue 5/19

7:43 pm-9:40 pm

Nonstop2h 57m

$254

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Fri 4/24

7:38 pm-10:57 pm

Nonstop2h 19m

Hartford Bradley Intl

Mon 4/27

7:29 pm-9:20 pm

Nonstop2h 51m

$268

MolineBoston

MLI - BOS

MLIBOS

Moline Quad-City

Tue 6/30

3:52 pm-9:56 pm

1 stop5h 04m

Boston Logan Intl

Sat 7/11

6:00 am-12:39 pm

1 stop7h 39m

$279

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Tue 3/17

6:45 am-11:51 pm

1 stop16h 06m

Hartford Bradley Intl

Sat 3/21

6:00 am-11:25 am

1 stop6h 25m

$280

MolineBoston

MLI - BOS

MLIBOS

Moline Quad-City

Fri 6/26

6:34 pm-12:59 am

1 stop5h 25m

Boston Logan Intl

Wed 7/1

7:19 am-12:39 pm

1 stop6h 20m

$282

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Massachusetts from

How to get the cheapest flight ticket from Illinois to Massachusetts

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Massachusetts?

In general, January is the cheapest month to fly from Illinois to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $190. If you aren’t able to travel to Massachusetts during the month of January, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $207.

What is the cheapest day to depart on your flight to Massachusetts?

According to our data, Thursday is the cheapest day to fly to Massachusetts from Illinois. The lowest ticket price found for a Thursday departure recently was $236. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Illinois because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $292.

What is the cheapest time of day to depart on your flight to Massachusetts?

Our data shows that the cheapest Illinois to Massachusetts flights are usually those with departure times in the evening. Our users have found flights to Massachusetts in the evening for as low as $213. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $290 on average. Flights to Massachusetts from Illinois at noon are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Illinois to Massachusetts flight route?

Fly from Chicago Midway to Boston Logan Intl for the best Illinois - Massachusetts flight prices

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

You are more likely to see cheaper flights to Massachusetts from Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around $228 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from Illinois for as low as $188 on momondo.

What cabin class options are available on Illinois to Massachusetts flights?

There are 4 cabin classes available to choose from on Illinois to Massachusetts flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Illinois to Massachusetts flights?

No. A direct flight is the cheapest option for a flight between Illinois to Massachusetts.

Cheap Illinois to Massachusetts flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Illinois to Massachusetts

Best Price Found

$88

Fastest flight time

1h 50m

Direct flights

Every day

Airports in Massachusetts

140 airports
The best one-way flight to Massachusetts from Illinois in the past 72 hours is $88. The best round-trip flight deal from Illinois to Massachusetts found on momondo in the last 72 hours is $147.
The fastest flight from Illinois to Massachusetts takes 1h 50m
Direct flights go from Illinois to Massachusetts every day.
There are 140 airports in Massachusetts. From Illinois there are direct flights to Albany Intl (ALB).
Search flight deals

  • When did momondo last update prices for flights from Illinois to Massachusetts?

    Prices for flights from Illinois to Massachusetts were last updated today.

  • How many operators does momondo search for flights from Illinois to Massachusetts?

  • How old do you have to be to fly from Illinois to Massachusetts?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Illinois to Massachusetts.

  • What documentation or ID do you need to fly to Massachusetts?

    The travel and health documents you'll need for your trip to Massachusetts may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Massachusetts. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Illinois to Massachusetts?

Best airlines flying from Illinois to Massachusetts

Compare and see reviews for airlines that fly from Illinois to Massachusetts with momondo
Airline
Rating
Free Cancellation
Price
JetBluePriceFrom $61Free CancellationRating
7.2
2,895 reviews
Search JetBlue flights
DeltaPriceFrom $88Free CancellationRating
7.9
8,242 reviews
Search Delta flights
Spirit AirlinesPriceFrom $91Free CancellationRating
6.3
8,490 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $117Free CancellationRating
7.4
9,378 reviews
Search United Airlines flights
American AirlinesPriceFrom $117Free CancellationRating
7.1
11,376 reviews
Search American Airlines flights
SouthwestPriceFrom $126Free CancellationRating
8.0
4,303 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Illinois to Massachusetts?

Finding the right flight to Massachusetts from Illinois is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Massachusetts quick and easy, saving you time and money.

Can I find flights from Illinois to Massachusetts with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Illinois to Massachusetts flights to just show those with flexible booking policies.

How can momondo help me find flights from Illinois to Massachusetts?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Massachusetts from Illinois.

I’m not ready to book a flight from Illinois to Massachusetts right now. Can momondo alert me if prices change?

Price alerts on flights to Massachusetts from Illinois are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Massachusetts trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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