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

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

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

As of September 2025, there are 543 flights per week flying from Illinois to Massachusetts. The most common day of the week flights depart is Tue, with 22% of flights taking off on this day.

What airlines fly to Massachusetts?

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Massachusetts from Illinois according to our data. American Airlines is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Massachusetts. Keep in mind that there are 7 different airlines that fly to Massachusetts on a routine basis, so you have a few additional options to choose from.

How long is the flight from Illinois to Massachusetts?

On average, it takes 2h 15m to fly from Illinois to Massachusetts if you fly out of Chicago (the most popular airport in Illinois) and into Boston (the most popular airport in Massachusetts). If you’re flying out of Moline and into Boston, then the flight time is around 4h 54m.

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

As of September 2025, 77 flights take off from Illinois and land in Massachusetts each day. The most common flight departure time for this route is 9:00AM, with 45% of daily flights taking off at noon.

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?

As of September 2025, there are 7 operators available to choose from 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.

$69 Cheap Flights from Illinois to Massachusetts in 2025/26

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Find the cheapest flights from Illinois to Massachusetts

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

6:30 am - 9:56 amORD-BOS

2h 26mnonstop

3:17 pm - 5:07 pmBOS-ORD

2h 50mnonstop

$127United Airlines

Find Deal

Sat, Oct 4 - Tue, Oct 7

12:30 pm - 5:45 pmMDW-BOS

4h 15m1 stop

5:20 am - 7:00 amBOS-MDW

2h 40mnonstop

$127Southwest

Find Deal

Wed, Oct 22 - Sat, Oct 25

7:13 pm - 10:46 pmORD-BOS

2h 33mnonstop

7:09 am - 9:22 amBOS-ORD

3h 13mnonstop

$135JetBlue

Find Deal

Fri, Oct 17 - Wed, Oct 22

8:38 pm - 12:06 amORD-BOS

2h 28mnonstop

5:29 pm - 7:43 pmBOS-ORD

3h 14mnonstop

$137JetBlue

Find Deal

Thu, Dec 4 - Mon, Dec 8

7:00 am - 10:20 amORD-BOS

2h 20mnonstop

7:02 am - 9:05 amBOS-ORD

3h 03mnonstop

$138American Airlines

Find Deal

Sat, Mar 7 - Mon, Mar 9

6:00 am - 1:20 pmORD-BOS

6h 20m1 stop

3:00 pm - 1:03 amBOS-ORD

11h 03m1 stop

$139Spirit Airlines

Find Deal

Tue, Oct 28 - Tue, Oct 28

10:49 am - 12:40 amORD-BOS

12h 51m1 stop

6:15 am - 5:04 pmBOS-ORD

11h 49m1 stop

$140Spirit Airlines

Find Deal

Wed, Nov 5 - Wed, Nov 12

8:25 pm - 11:54 pmORD-BOS

2h 29mnonstop

6:47 am - 8:45 amBOS-ORD

2h 58mnonstop

$145American Airlines

Find Deal

Fri, Oct 24 - Tue, Oct 28

7:05 am - 10:29 amORD-BOS

2h 24mnonstop

7:30 pm - 9:19 pmBOS-ORD

2h 49mnonstop

$157Delta

Find Deal

Thu, Oct 23 - Tue, Oct 28

7:15 pm - 10:45 pmORD-BOS

2h 30mnonstop

12:05 pm - 2:02 pmBOS-ORD

2h 57mnonstop

$158Delta

Find Deal

Mon, Nov 24 - Thu, Nov 27

United Airlines flights from Illinois to Massachusetts

Our best United Airlines deals on Illinois to Massachusetts flight tickets

United Airlines

Oct 4

ORD6:30 amChicago O'Hare Intl

2h 26m

BOS9:56 amBoston Logan Intl

Oct 7

BOS3:17 pmBoston Logan Intl

2h 50m

ORD5:07 pmChicago O'Hare Intl

$127

Find similar

United Airlines

Nov 7

ORD9:25 pmChicago O'Hare Intl

2h 20m

BOS12:45 amBoston Logan Intl

Nov 10

BOS12:25 pmBoston Logan Intl

3h 00m

ORD2:25 pmChicago O'Hare Intl

$131

Find similar

United Airlines

Nov 7

ORD9:25 pmChicago O'Hare Intl

2h 20m

BOS12:45 amBoston Logan Intl

Nov 15

BOS6:00 amBoston Logan Intl

3h 00m

ORD8:00 amChicago O'Hare Intl

$134

Find similar

Southwest flights from Illinois to Massachusetts

Our best Southwest deals on Illinois to Massachusetts flight tickets

Southwest

Oct 22

MDW12:30 pmChicago Midway

4h 15m

1 stop

BOS5:45 pmBoston Logan Intl

Oct 25

BOS5:20 amBoston Logan Intl

2h 40m

MDW7:00 amChicago Midway

$127

Find similar

Southwest

Oct 22

MDW6:05 amChicago Midway

2h 15m

BOS9:20 amBoston Logan Intl

Oct 25

BOS5:05 amBoston Logan Intl

8h 15m

2 stops

MDW12:20 pmChicago Midway

$132

Find similar

Southwest

Nov 7

MDW1:50 pmChicago Midway

8h 50m

1 stop

BOS11:40 pmBoston Logan Intl

Nov 9

BOS5:15 amBoston Logan Intl

2h 45m

MDW7:00 amChicago Midway

$133

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 10/4

6:30 am-9:56 am

Nonstop2h 26m

Boston Logan Intl

Tue 10/7

3:17 pm-5:07 pm

Nonstop2h 50m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 10/22

12:30 pm-5:45 pm

1 stop4h 15m

Boston Logan Intl

Sat 10/25

5:20 am-7:00 am

Nonstop2h 40m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 10/17

7:13 pm-10:46 pm

Nonstop2h 33m

Boston Logan Intl

Wed 10/22

7:09 am-9:22 am

Nonstop3h 13m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 12/4

8:38 pm-12:06 am

Nonstop2h 28m

Boston Logan Intl

Mon 12/8

5:29 pm-7:43 pm

Nonstop3h 14m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 3/7

7:00 am-10:20 am

Nonstop2h 20m

Boston Logan Intl

Mon 3/9

7:02 am-9:05 am

Nonstop3h 03m

$138

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 10/28

6:00 am-1:20 pm

1 stop6h 20m

Boston Logan Intl

Tue 10/28

3:00 pm-1:03 am

1 stop11h 03m

$139

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 11/5

10:49 am-12:40 am

1 stop12h 51m

Boston Logan Intl

Wed 11/12

6:15 am-5:04 pm

1 stop11h 49m

$140

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 10/24

8:25 pm-11:54 pm

Nonstop2h 29m

Boston Logan Intl

Tue 10/28

6:47 am-8:45 am

Nonstop2h 58m

$145

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 10/23

7:05 am-10:29 am

Nonstop2h 24m

Boston Logan Intl

Tue 10/28

7:30 pm-9:19 pm

Nonstop2h 49m

$157

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 11/24

7:15 pm-10:45 pm

Nonstop2h 30m

Boston Logan Intl

Thu 11/27

12:05 pm-2:02 pm

Nonstop2h 57m

$158

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 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

Prices

Airlines

Other information

What is the cheapest month to fly to Massachusetts?

In general, September 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 $207. If you aren’t able to travel to Massachusetts 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 $217.

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 $243. 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 $309.

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 $225. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $302 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 O'Hare Intl 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 $235 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 $190 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	$68
Fastest flight time	1h 50m
Direct flights	Every day
Airports in Massachusetts	2 airports

The best one-way flight to Massachusetts from Illinois in the past 72 hours is $68. The best round-trip flight deal from Illinois to Massachusetts found on momondo in the last 72 hours is $167.

The fastest flight from Illinois to Massachusetts takes 1h 50m

Direct flights go from Illinois to Massachusetts every day.

There are 2 airports near Massachusetts: Albany Intl (ALB), Hartford Bradley Intl (BDL)

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?
As of September 2025, there are 7 operators available to choose from 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?
Based on momondo bookings for flights between Illinois and Massachusetts, the leading plane model is Boeing 737-800, making up 25.27% of the total bookings. Other popular models include Embraer 175 with 12.12%, Airbus A220-300 with 12.12%, and Boeing 737-900 with 11.96%.

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
Spirit Airlines	PriceFrom $46	Free Cancellation	Rating 6.3 8,041 reviews	Search Spirit Airlines flights
JetBlue	PriceFrom $78	Free Cancellation	Rating 7.2 2,912 reviews	Search JetBlue flights
Delta	PriceFrom $96	Free Cancellation	Rating 7.9 7,974 reviews	Search Delta flights
Frontier	PriceFrom $100	Free Cancellation	Rating 5.8 3,165 reviews	Search Frontier flights
American Airlines	PriceFrom $118	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $127	Free Cancellation	Rating 7.4 8,926 reviews	Search United Airlines flights
Southwest	PriceFrom $139	Free Cancellation	Rating 8.0 4,244 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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Find better results for your trip to Massachusetts

Popular cities in Massachusetts

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Cheap flights from Illinois to Massachusetts from $69

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 9/30. 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

Price Alerts

Price Alerts

Find the cheapest flights from Illinois to Massachusetts

Cheap round-trip flights

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Cheap last minute flights

Cheap direct flights

United Airlines flights from Illinois to Massachusetts

Our best United Airlines deals on Illinois to Massachusetts flight tickets

Southwest flights from Illinois to Massachusetts

Our best Southwest deals on Illinois to Massachusetts flight tickets

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

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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?

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

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

What is the cheapest Illinois to Massachusetts flight route?

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

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

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.

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

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

What airlines fly to Massachusetts?

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

As of September 2025, 77 flights take off from Illinois and land in Massachusetts each day. The most common flight departure time for this route is 9:00AM, with 45% of daily flights taking off at noon.

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

As of September 2025, there are 543 flights per week flying from Illinois to Massachusetts. The most common day of the week flights depart is Tue, with 22% of flights taking off on this day.

How long is the flight from Illinois to Massachusetts?

On average, it takes 2h 15m to fly from Illinois to Massachusetts if you fly out of Chicago (the most popular airport in Illinois) and into Boston (the most popular airport in Massachusetts). If you’re flying out of Moline and into Boston, then the flight time is around 4h 54m.

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

Fastest flight time

Direct flights

Airports in Massachusetts

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

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?

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

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

Why use momondo?

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

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

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

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

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.

Get notified when prices go down

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

Find better results for your trip to Massachusetts

Popular cities in Massachusetts

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