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Cheap flights from Massachusetts to Illinois from $55

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 8/20. 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 Massachusetts to Illinois

Cheap round-trip flights

Spirit Airlines Logo
6:05 am - 7:07 pmBOS-ORD
14h 02m1 stop
Spirit Airlines Logo
11:57 am - 11:57 pmORD-BOS
11h 00m1 stop
$112Spirit Airlines
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Wed, Sep 3 - Tue, Sep 9
United Airlines Logo
6:10 am - 8:05 amBOS-ORD
2h 55mnonstop
United Airlines Logo
9:15 pm - 12:45 amORD-BOS
2h 30mnonstop
$117United Airlines
Find Deal
Tue, Sep 2 - Thu, Sep 4
Southwest Logo
8:35 am - 10:10 amBOS-MDW
2h 35mnonstop
Southwest Logo
10:00 am - 1:25 pmMDW-BOS
2h 25mnonstop
$127Southwest
Find Deal
Thu, Sep 4 - Sun, Sep 7
JetBlue Logo
7:00 am - 8:56 amBOS-ORD
2h 56mnonstop
JetBlue Logo
9:51 am - 1:20 pmORD-BOS
2h 29mnonstop
$129JetBlue
Find Deal
Sat, Sep 6 - Wed, Sep 10
Southwest Logo
12:20 pm - 1:55 pmBOS-MDW
2h 35mnonstop
Southwest Logo
6:25 am - 3:25 pmMDW-BOS
8h 00m1 stop
$133Southwest
Find Deal
Sat, Aug 30 - Tue, Sep 2
American Airlines Logo
5:00 am - 6:51 amBOS-ORD
2h 51mnonstop
American Airlines Logo
5:36 pm - 9:00 pmORD-BOS
2h 24mnonstop
$136American Airlines
Find Deal
Sat, Sep 13 - Sat, Sep 20
American Airlines Logo
5:00 am - 6:51 amBOS-ORD
2h 51mnonstop
American Airlines Logo
6:05 am - 9:32 amORD-BOS
2h 27mnonstop
$138American Airlines
Find Deal
Sun, Sep 14 - Sun, Sep 21
Delta Logo
7:55 pm - 9:56 pmBOS-ORD
3h 01mnonstop
Delta Logo
10:15 am - 1:48 pmORD-BOS
2h 33mnonstop
$147Delta
Find Deal
Thu, Sep 4 - Sat, Sep 6
JetBlue Logo
2:45 pm - 8:49 pmBOS-ORD
7h 04m1 stop
JetBlue Logo
7:50 pm - 11:25 pmORD-BOS
2h 35mnonstop
$169JetBlue
Find Deal
Fri, Sep 12 - Fri, Sep 19
Delta Logo
7:25 am - 9:15 amBOS-ORD
2h 50mnonstop
Delta Logo
6:59 pm - 10:40 pmORD-BOS
2h 41mnonstop
$173Delta
Find Deal
Thu, Oct 2 - Fri, Oct 3

JetBlue flights from Massachusetts to Illinois

Our best JetBlue deals on Massachusetts to Illinois flight tickets
JetBlue
Sep 6
BOS7:00 amBoston Logan Intl
2h 56m
ORD8:56 amChicago O'Hare Intl
Sep 10
ORD9:51 amChicago O'Hare Intl
2h 29m
BOS1:20 pmBoston Logan Intl
$129
Find similar
JetBlue
Aug 5
BOS6:00 amBoston Logan Intl
2h 55m
ORD7:55 amChicago O'Hare Intl
Aug 14
ORD8:40 amChicago O'Hare Intl
2h 24m
BOS12:04 pmBoston Logan Intl
$137
Find similar
JetBlue
Sep 12
BOS2:45 pmBoston Logan Intl
7h 04m
1 stop
ORD8:49 pmChicago O'Hare Intl
Sep 19
ORD7:50 pmChicago O'Hare Intl
2h 35m
BOS11:25 pmBoston Logan Intl
$169
Find similar

Spirit Airlines flights from Massachusetts to Illinois

Our best Spirit Airlines deals on Massachusetts to Illinois flight tickets
Spirit Airlines
Sep 3
BOS6:05 amBoston Logan Intl
14h 02m
1 stop
ORD7:07 pmChicago O'Hare Intl
Sep 9
ORD11:57 amChicago O'Hare Intl
11h 00m
1 stop
BOS11:57 pmBoston Logan Intl
$112
Find similar
Spirit Airlines
Aug 20
BOS6:05 amBoston Logan Intl
14h 02m
1 stop
ORD7:07 pmChicago O'Hare Intl
Aug 26
ORD8:12 pmChicago O'Hare Intl
14h 06m
1 stop
BOS11:18 amBoston Logan Intl
$121
Find similar
Spirit Airlines
Sep 9
BOS12:20 pmBoston Logan Intl
10h 38m
1 stop
ORD9:58 pmChicago O'Hare Intl
Sep 16
ORD11:57 amChicago O'Hare Intl
11h 00m
1 stop
BOS11:57 pmBoston Logan Intl
$124
Find similar

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 July 31, 2025.
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

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 9/3

6:05 am-7:07 pm

1 stop14h 02m

Chicago O'Hare Intl

Tue 9/9

11:57 am-11:57 pm

1 stop11h 00m

$112

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 9/2

6:10 am-8:05 am

Nonstop2h 55m

Chicago O'Hare Intl

Thu 9/4

9:15 pm-12:45 am

Nonstop2h 30m

$117

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 9/4

8:35 am-10:10 am

Nonstop2h 35m

Chicago Midway

Sun 9/7

10:00 am-1:25 pm

Nonstop2h 25m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 9/6

7:00 am-8:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Wed 9/10

9:51 am-1:20 pm

Nonstop2h 29m

$129

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 8/30

12:20 pm-1:55 pm

Nonstop2h 35m

Chicago Midway

Tue 9/2

6:25 am-3:25 pm

1 stop8h 00m

$133

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 9/13

5:00 am-6:51 am

Nonstop2h 51m

Chicago O'Hare Intl

Sat 9/20

5:36 pm-9:00 pm

Nonstop2h 24m

$136

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 9/14

5:00 am-6:51 am

Nonstop2h 51m

Chicago O'Hare Intl

Sun 9/21

6:05 am-9:32 am

Nonstop2h 27m

$138

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/4

7:55 pm-9:56 pm

Nonstop3h 01m

Chicago O'Hare Intl

Sat 9/6

10:15 am-1:48 pm

Nonstop2h 33m

$147

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 9/12

2:45 pm-8:49 pm

1 stop7h 04m

Chicago O'Hare Intl

Fri 9/19

7:50 pm-11:25 pm

Nonstop2h 35m

$169

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 10/2

7:25 am-9:15 am

Nonstop2h 50m

Chicago O'Hare Intl

Fri 10/3

6:59 pm-10:40 pm

Nonstop2h 41m

$173

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 $177, 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 $194.

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

The cheapest day to depart from Massachusetts to Illinois is on a Friday when prices can be found for as low as $312. Flights from Massachusetts to Illinois on a Sunday will generally be more expensive and average around $421. 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 $268. Flights in the afternoon are often more expensive with an average ticket price of $350.

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 $243 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 $211 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

$55

Fastest flight time

2h 05m

Direct flights

Every day

Airports in Illinois

3 airports
The best one-way flight to Illinois from Massachusetts in the past 72 hours is $55. The best round-trip flight deal from Massachusetts to Illinois found on momondo in the last 72 hours is $112.
The fastest flight from Massachusetts to Illinois takes 2h 05m
Direct flights go from Massachusetts to Illinois every day.
There are 3 airports near Illinois: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Lambert-St Louis (STL)
Search flight deals

  • 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 $37Free CancellationRating
6.3
8,049 reviews
Search Spirit Airlines flights
JetBluePriceFrom $74Free CancellationRating
7.2
2,914 reviews
Search JetBlue flights
DeltaPriceFrom $94Free CancellationRating
8.0
7,981 reviews
Search Delta flights
United AirlinesPriceFrom $97Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights
FrontierPriceFrom $100Free CancellationRating
5.9
3,239 reviews
Search Frontier flights
SouthwestPriceFrom $125Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
American AirlinesPriceFrom $136Free CancellationRating
7.2
10,000 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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