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Cheap flights from Massachusetts to Illinois from $68

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Massachusetts to Illinois departing on 4/22. 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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Find the cheapest flights from Massachusetts to Illinois

Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
7:02 am - 8:59 am
BOS
-
ORD
2h 57mnonstop
JetBlue Logo
6:00 am - 9:15 am
ORD
-
BOS
2h 15mnonstop
$137JetBlue
Thu, Apr 30 - Sun, May 3
JetBlue Logo
7:02 am - 8:59 am
BOS
-
ORD
2h 57mnonstop
JetBlue Logo
6:00 am - 9:15 am
ORD
-
BOS
2h 15mnonstop
$138JetBlue
Thu, Apr 30 - Sun, May 3
Frontier Logo
12:52 pm - 10:14 pm
BOS
-
MDW
10h 22m
1 stop
Frontier Logo
12:27 pm - 1:24 am
MDW
-
BOS
11h 57m
1 stop
$140Frontier
Tue, Apr 28 - Tue, May 5
Southwest Logo
6:20 pm - 8:10 pm
BOS
-
MDW
2h 50mnonstop
Southwest Logo
3:15 pm - 6:35 pm
MDW
-
BOS
2h 20mnonstop
$157Southwest
Tue, Apr 28 - Tue, May 5
Southwest Logo
6:20 pm - 8:10 pm
BOS
-
MDW
2h 50mnonstop
Southwest Logo
3:50 pm - 11:15 pm
MDW
-
BOS
6h 25m
1 stop
$167Southwest
Wed, May 13 - Mon, Jun 1
United Airlines Logo
4:55 pm - 6:30 pm
ALB
-
ORD
2h 35mnonstop
United Airlines Logo
12:00 pm - 3:04 pm
ORD
-
ALB
2h 04mnonstop
$285United Airlines
Tue, Apr 28 - Tue, May 5
American Airlines Logo
11:57 am - 1:51 pm
ALB
-
ORD
2h 54mnonstop
American Airlines Logo
8:15 am - 11:27 am
ORD
-
ALB
2h 12mnonstop
$287American Airlines
Wed, Apr 22 - Sat, Apr 25
United Airlines Logo
4:55 pm - 6:31 pm
ALB
-
ORD
2h 36mnonstop
United Airlines Logo
6:02 pm - 9:12 pm
ORD
-
ALB
2h 10mnonstop
$289United Airlines
Wed, May 6 - Sat, May 9
American Airlines Logo
7:21 pm - 9:18 pm
ALB
-
ORD
2h 57mnonstop
American Airlines Logo
8:39 am - 3:47 pm
ORD
-
ALB
6h 08m
1 stop
$297American Airlines
Wed, Apr 22 - Sat, Apr 25
Delta Logo
6:00 am - 9:29 am
ALB
-
STL
4h 29m
1 stop
Delta Logo
6:04 pm - 11:18 pm
STL
-
ALB
4h 14m
1 stop
$348Delta
Thu, May 14 - Tue, May 19

Delta flights from Massachusetts to Illinois

Our best Delta deals on Massachusetts to Illinois flight tickets
Delta
Apr 30
BOS7:10 amBoston Logan Intl
3h 05m
ORD9:15 amChicago O'Hare Intl
May 3
ORD6:50 amChicago O'Hare Intl
2h 21m
BOS10:11 amBoston Logan Intl
$157
Delta
Apr 11
BOS7:15 amBoston Logan Intl
3h 09m
ORD9:24 amChicago O'Hare Intl
Apr 12
ORD7:00 amChicago O'Hare Intl
2h 25m
BOS10:25 amBoston Logan Intl
$158
Delta
Apr 8
BOS7:15 amBoston Logan Intl
3h 10m
ORD9:25 amChicago O'Hare Intl
Apr 16
ORD6:50 amChicago O'Hare Intl
2h 21m
BOS10:11 amBoston Logan Intl
$187

JetBlue flights from Massachusetts to Illinois

Our best JetBlue deals on Massachusetts to Illinois flight tickets
JetBlue
Apr 30
BOS7:02 amBoston Logan Intl
2h 57m
ORD8:59 amChicago O'Hare Intl
May 3
ORD6:00 amChicago O'Hare Intl
2h 15m
BOS9:15 amBoston Logan Intl
$137
JetBlue
Apr 30
BOS7:02 amBoston Logan Intl
2h 57m
ORD8:59 amChicago O'Hare Intl
May 3
ORD6:00 amChicago O'Hare Intl
2h 15m
BOS9:15 amBoston Logan Intl
$138
JetBlue
May 26
BOS5:25 pmBoston Logan Intl
3h 10m
ORD7:35 pmChicago O'Hare Intl
May 28
ORD8:30 pmChicago O'Hare Intl
2h 29m
BOS11:59 pmBoston Logan Intl
$143

momondo Fare Finder

 
Customize your flight search to find flights from Massachusetts to Illinois 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 April 2, 2026.
Use the filters below to find and compare flights from Massachusetts to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/30

7:02 am-8:59 am

Nonstop2h 57m

Chicago O'Hare Intl

Sun 5/3

6:00 am-9:15 am

Nonstop2h 15m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/30

7:02 am-8:59 am

Nonstop2h 57m

Chicago O'Hare Intl

Sun 5/3

6:00 am-9:15 am

Nonstop2h 15m

$138

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 4/28

12:52 pm-10:14 pm

1 stop10h 22m

Chicago Midway

Tue 5/5

12:27 pm-1:24 am

1 stop11h 57m

$140

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 4/28

6:20 pm-8:10 pm

Nonstop2h 50m

Chicago Midway

Tue 5/5

3:15 pm-6:35 pm

Nonstop2h 20m

$157

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 5/13

6:20 pm-8:10 pm

Nonstop2h 50m

Chicago Midway

Mon 6/1

3:50 pm-11:15 pm

1 stop6h 25m

$167
Quickest round-trip

AlbanyChicago

ALB - ORD

ALBORD

Albany Intl

Tue 4/28

4:55 pm-6:30 pm

Nonstop2h 35m

Chicago O'Hare Intl

Tue 5/5

12:00 pm-3:04 pm

Nonstop2h 04m

$285

AlbanyChicago

ALB - ORD

ALBORD

Albany Intl

Wed 4/22

11:57 am-1:51 pm

Nonstop2h 54m

Chicago O'Hare Intl

Sat 4/25

8:15 am-11:27 am

Nonstop2h 12m

$287

AlbanyChicago

ALB - ORD

ALBORD

Albany Intl

Wed 5/6

4:55 pm-6:31 pm

Nonstop2h 36m

Chicago O'Hare Intl

Sat 5/9

6:02 pm-9:12 pm

Nonstop2h 10m

$289

AlbanyChicago

ALB - ORD

ALBORD

Albany Intl

Wed 4/22

7:21 pm-9:18 pm

Nonstop2h 57m

Chicago O'Hare Intl

Sat 4/25

8:39 am-3:47 pm

1 stop6h 08m

$297

AlbanySt. Louis

ALB - STL

ALBSTL

Albany Intl

Thu 5/14

6:00 am-9:29 am

1 stop4h 29m

Lambert-St Louis

Tue 5/19

6:04 pm-11:18 pm

1 stop4h 14m

$348

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 Illinois from

How to get the cheapest flight ticket from Massachusetts to Illinois

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 Illinois?

The cheapest month to fly to Illinois from Massachusetts is in September. Flight prices, which tend to average around $187, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of September, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $200.

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

The cheapest day to depart from Massachusetts to Illinois is on a Wednesday when prices can be found for as low as $313. Flights from Massachusetts to Illinois on a Sunday will generally be more expensive and average around $402. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

Our most recent data shows that the best time of day to fly to Illinois is in the evening. Flights from Massachusetts to Illinois during this time can be as low as $269. Flights at noon are often more expensive with an average ticket price of $371.

What is the cheapest Massachusetts to Illinois flight route?

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

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

You are more likely to see cheaper flights to Illinois from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Illinois for around $246 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Illinois from Massachusetts for as low as $210 on momondo.

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

There are 4 cabin classes available to choose from on Massachusetts to Illinois 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 Massachusetts to Illinois flights?

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

Cheap Massachusetts to Illinois flight deals and tips

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

Best Price Found

$129

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Illinois

98 airports
The best one-way flight to Illinois from Massachusetts in the past 72 hours is $129. The best round-trip flight deal from Massachusetts to Illinois found on momondo in the last 72 hours is $239.
The fastest flight from Massachusetts to Illinois takes 2h 10m
Direct flights go from Massachusetts to Illinois every day.
There are 98 airports in Illinois. From Massachusetts there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

Frequently asked questions about flying from Massachusetts to Illinois

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

    Prices for flights from Massachusetts to Illinois refresh daily.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Massachusetts to Illinois.

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

    The travel and health documents required for your trip to Illinois can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Illinois. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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

Best airlines flying from Massachusetts to Illinois

Compare and see reviews for airlines that fly from Massachusetts to Illinois with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $32Free CancellationRating
6.3
8,577 reviews
Search Spirit Airlines flights
JetBluePriceFrom $67Free CancellationRating
7.2
2,909 reviews
Search JetBlue flights
DeltaPriceFrom $84Free CancellationRating
7.9
8,366 reviews
Search Delta flights
SouthwestPriceFrom $117Free CancellationRating
8.0
4,337 reviews
Search Southwest flights
United AirlinesPriceFrom $117Free CancellationRating
7.4
9,535 reviews
Search United Airlines flights
American AirlinesPriceFrom $128Free CancellationRating
7.1
11,549 reviews
Search American Airlines flights

Why use momondo?

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

It is quick and easy to find Massachusetts to Illinois flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Illinois that suits you.

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

momondo does allow users to show only those flights to Illinois from Massachusetts which offer a flexible booking policy as well as other useful filters and features.

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

Once all potential Massachusetts to Illinois flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Yes. momondo can track prices for Massachusetts to Illinois flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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