How many flights depart from Massachusetts to Illinois on average per week?

749 flights are operational weekly from Massachusetts to Illinois as of September 2025. The most popular departure day for this route is Thu, with 19% of flights per week taking off on this day.

What airlines fly to Illinois?

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Illinois from Massachusetts according to our data. American Airlines is the first choice among our users, with 40% of people opting to fly with this airline when traveling to Illinois. Keep in mind that there are 7 different airlines that fly to Illinois on a routine basis, so you have a few additional options to choose from.

How many flights depart from Massachusetts to Illinois on average per day?

As of September 2025, there are 107 flights per day flying from Massachusetts to Illinois. The most common time of day flights depart is 7:00AM, with 41% of flights taking off at noon.

How long is the flight from Massachusetts to Illinois?

The flight from Massachusetts to Illinois depends on which airports you’re departing and arriving from and whether or not you have a layover. If you fly from Boston (a popular airport in Massachusetts) to Chicago O'Hare Intl Airport (the most popular airport in Illinois), then the flight time is 2h 48m on average. If you fly from Worcester (another popular airport in Massachusetts) to Chicago O'Hare Intl Airport, then the average flight time is 5h 07m.

What is the cheapest airline that flies from Massachusetts to Illinois?

United Airlines, Frontier, and Southwest are the most popular carriers operating 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?

The number of operators available for flights from Massachusetts to Illinois is 7 as of September 2025.

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.

$64 Cheap Flights from Massachusetts to Illinois in 2025/26

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Find the cheapest flights from Massachusetts to Illinois

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

3:00 pm - 11:45 pmBOS-ORD

9h 45m1 stop

6:00 am - 1:20 pmORD-BOS

6h 20m1 stop

$126Spirit Airlines

Find Deal

Wed, Oct 15 - Tue, Oct 21

8:15 am - 11:40 amBOS-MDW

4h 25m1 stop

6:05 am - 9:20 amMDW-BOS

2h 15mnonstop

$127Southwest

Find Deal

Sat, Oct 25 - Sun, Oct 26

12:45 pm - 2:45 pmBOS-ORD

3h 00mnonstop

7:10 am - 10:35 amORD-BOS

2h 25mnonstop

$127Delta

Find Deal

Wed, Nov 19 - Fri, Nov 28

6:00 am - 7:56 amBOS-ORD

2h 56mnonstop

6:30 am - 9:56 amORD-BOS

2h 26mnonstop

$131United Airlines

Find Deal

Wed, Oct 15 - Sun, Oct 19

6:00 am - 7:56 amBOS-ORD

2h 56mnonstop

6:30 am - 9:56 amORD-BOS

2h 26mnonstop

$133United Airlines

Find Deal

Thu, Oct 16 - Sun, Oct 19

7:09 am - 9:22 amBOS-ORD

3h 13mnonstop

7:13 pm - 10:46 pmORD-BOS

2h 33mnonstop

$135JetBlue

Find Deal

Wed, Oct 15 - Wed, Oct 15

5:15 pm - 7:27 pmBOS-ORD

3h 12mnonstop

12:28 pm - 3:54 pmORD-BOS

2h 26mnonstop

$137JetBlue

Find Deal

Thu, Nov 20 - Thu, Nov 27

5:24 am - 7:25 amBOS-ORD

3h 01mnonstop

6:05 am - 9:32 amORD-BOS

2h 27mnonstop

$145American Airlines

Find Deal

Wed, Oct 15 - Mon, Oct 20

6:57 am - 8:55 amBOS-ORD

2h 58mnonstop

6:05 am - 9:32 amORD-BOS

2h 27mnonstop

$146American Airlines

Find Deal

Thu, Oct 23 - Sun, Oct 26

7:30 am - 9:34 amBOS-ORD

3h 04mnonstop

7:10 am - 10:35 amORD-BOS

2h 25mnonstop

$157Delta

Find Deal

Sun, Nov 23 - Fri, Nov 28

Delta flights from Massachusetts to Illinois

Our best Delta deals on Massachusetts to Illinois flight tickets

Delta

Nov 19

BOS12:45 pmBoston Logan Intl

3h 00m

ORD2:45 pmChicago O'Hare Intl

Nov 28

ORD7:10 amChicago O'Hare Intl

2h 25m

BOS10:35 amBoston Logan Intl

$127

Find similar

Delta

Nov 23

BOS7:30 amBoston Logan Intl

3h 04m

ORD9:34 amChicago O'Hare Intl

Nov 28

ORD7:10 amChicago O'Hare Intl

2h 25m

BOS10:35 amBoston Logan Intl

$157

Find similar

Delta

Oct 23

BOS7:20 amBoston Logan Intl

3h 02m

ORD9:22 amChicago O'Hare Intl

Oct 26

ORD7:05 amChicago O'Hare Intl

2h 24m

BOS10:29 amBoston Logan Intl

$167

Find similar

JetBlue flights from Massachusetts to Illinois

Our best JetBlue deals on Massachusetts to Illinois flight tickets

JetBlue

Oct 1

BOS7:00 amBoston Logan Intl

2h 56m

ORD8:56 amChicago O'Hare Intl

Oct 15

ORD7:13 pmChicago O'Hare Intl

2h 33m

BOS10:46 pmBoston Logan Intl

$127

Find similar

JetBlue

Oct 15

BOS7:09 amBoston Logan Intl

3h 13m

ORD9:22 amChicago O'Hare Intl

Oct 15

ORD7:13 pmChicago O'Hare Intl

2h 33m

BOS10:46 pmBoston Logan Intl

$135

Find similar

JetBlue

Nov 20

BOS5:15 pmBoston Logan Intl

3h 12m

ORD7:27 pmChicago O'Hare Intl

Nov 27

ORD12:28 pmChicago O'Hare Intl

2h 26m

BOS3:54 pmBoston Logan Intl

$137

Find similar

Fly from

Fly to

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 10/15

3:00 pm-11:45 pm

1 stop9h 45m

Chicago O'Hare Intl

Tue 10/21

6:00 am-1:20 pm

1 stop6h 20m

$126

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 10/25

8:15 am-11:40 am

1 stop4h 25m

Chicago Midway

Sun 10/26

6:05 am-9:20 am

Nonstop2h 15m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 11/19

12:45 pm-2:45 pm

Nonstop3h 00m

Chicago O'Hare Intl

Fri 11/28

7:10 am-10:35 am

Nonstop2h 25m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 10/15

6:00 am-7:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Sun 10/19

6:30 am-9:56 am

Nonstop2h 26m

$131

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 10/16

6:00 am-7:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Sun 10/19

6:30 am-9:56 am

Nonstop2h 26m

$133

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 10/15

7:09 am-9:22 am

Nonstop3h 13m

Chicago O'Hare Intl

Wed 10/15

7:13 pm-10:46 pm

Nonstop2h 33m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 11/20

5:15 pm-7:27 pm

Nonstop3h 12m

Chicago O'Hare Intl

Thu 11/27

12:28 pm-3:54 pm

Nonstop2h 26m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 10/15

5:24 am-7:25 am

Nonstop3h 01m

Chicago O'Hare Intl

Mon 10/20

6:05 am-9:32 am

Nonstop2h 27m

$145

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 10/23

6:57 am-8:55 am

Nonstop2h 58m

Chicago O'Hare Intl

Sun 10/26

6:05 am-9:32 am

Nonstop2h 27m

$146

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 11/23

7:30 am-9:34 am

Nonstop3h 04m

Chicago O'Hare Intl

Fri 11/28

7:10 am-10:35 am

Nonstop2h 25m

$157

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

What is the cheapest month to fly to Illinois?

The cheapest month to fly to Illinois from Massachusetts is in January. Flight prices, which tend to average around $196, 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 January, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $199.

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 $322. Flights from Massachusetts to Illinois on a Sunday will generally be more expensive and average around $426. 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 $274. Flights in the morning are often more expensive with an average ticket price of $351.

What is the cheapest Massachusetts to Illinois flight route?

Fly from Boston Logan Intl to Chicago O'Hare Intl 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 $249 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 $216 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	$106
Fastest flight time	2h 10m
Direct flights	Every day
Airports in Illinois	2 airports

The best one-way flight to Illinois from Massachusetts in the past 72 hours is $106. The best round-trip flight deal from Massachusetts to Illinois found on momondo in the last 72 hours is $204.

The fastest flight from Massachusetts to Illinois takes 2h 10m

Direct flights go from Massachusetts to Illinois every day.

There are 2 airports near Illinois: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

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?
The number of operators available for flights from Massachusetts to Illinois is 7 as of September 2025.
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?
momondo data reveals that the most frequently booked plane model on the route from Massachusetts to Illinois is Boeing 737-800, representing 26.64% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 13.27%, Boeing 737-900 at 11.54%, and Airbus A220-300 at 10.18%.

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 Airlines	PriceFrom $67	Free Cancellation	Rating 6.3 8,045 reviews	Search Spirit Airlines flights
JetBlue	PriceFrom $84	Free Cancellation	Rating 7.2 2,911 reviews	Search JetBlue flights
United Airlines	PriceFrom $97	Free Cancellation	Rating 7.4 8,928 reviews	Search United Airlines flights
Frontier	PriceFrom $100	Free Cancellation	Rating 5.8 3,163 reviews	Search Frontier flights
Delta	PriceFrom $111	Free Cancellation	Rating 7.9 7,973 reviews	Search Delta flights
Southwest	PriceFrom $118	Free Cancellation	Rating 8.0 4,246 reviews	Search Southwest flights
American Airlines	PriceFrom $137	Free Cancellation	Rating 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.

An easier way to manage your Illinois 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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Find better results for your trip to Illinois

Popular cities in Illinois

Flights to New Yorkfrom $50

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Flights to Chicagofrom $65

Flights to Orlandofrom $57

Flights to Las Vegasfrom $47

Flights to San Franciscofrom $59

Flights to Washington, D.C.from $60

Flights to Bostonfrom $68

Flights to Atlantafrom $51

Flights to Dallasfrom $60

Flights to Seattlefrom $86

Massachusetts flight routes

Flights from Boston Logan Intl to Asheville Regional

Flights from Boston Logan Intl to Cleveland Hopkins Intl

Flights from Boston Logan Intl to West Tisbury Martha's Vineyard

Flights from Boston Logan Intl to Savannah/Hilton Head

Flights from Boston Logan Intl to Raleigh-Durham

Flights from Boston Logan Intl to Detroit Metropolitan Wayne County

Cheap flights from Massachusetts to Illinois from $64

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 11/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

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Price Alerts

Find the cheapest flights from Massachusetts to Illinois

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Delta flights from Massachusetts to Illinois

Our best Delta deals on Massachusetts to Illinois flight tickets

JetBlue flights from Massachusetts to Illinois

Our best JetBlue deals on Massachusetts to Illinois flight tickets

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Use the filters below to find and compare flights from Massachusetts to Illinois that are best for you.

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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?

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

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 $274. Flights in the morning are often more expensive with an average ticket price of $351.

What is the cheapest Massachusetts to Illinois flight route?

Fly from Boston Logan Intl to Chicago O'Hare Intl for the best Massachusetts - Illinois flight prices

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

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.

What is the cheapest airline that flies from Massachusetts to Illinois?

United Airlines, Frontier, and Southwest are the most popular carriers operating from Massachusetts to Illinois

What airlines fly to Illinois?

How many flights depart from Massachusetts to Illinois on average per day?

As of September 2025, there are 107 flights per day flying from Massachusetts to Illinois. The most common time of day flights depart is 7:00AM, with 41% of flights taking off at noon.

How many flights depart from Massachusetts to Illinois on average per week?

749 flights are operational weekly from Massachusetts to Illinois as of September 2025. The most popular departure day for this route is Thu, with 19% of flights per week taking off on this day.

How long is the flight from 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

Fastest flight time

Direct flights

Airports in Illinois

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

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?

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

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

Why use momondo?

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

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

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

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

An easier way to manage your Illinois 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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Illinois

Popular cities in Illinois

Popular flights according to clicks in the last 7 days on momondo