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

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

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

As of July 2025, there are 610 flights per week flying from Illinois to Massachusetts. The most common day of the week flights depart is Thu, with 23% 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 38% 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 Peoria and into Boston, then the flight time is around 5h.

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

As of July 2025, 87 flights take off from Illinois and land in Massachusetts each day. The most common flight departure time for this route is 8:00AM, with 42% 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 July 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.

$55 Cheap Flights from Illinois to Massachusetts in 2025

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Find the cheapest flights from Illinois to Massachusetts

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

11:36 am - 11:49 pmORD-BOS

11h 13m1 stop

6:05 am - 7:07 pmBOS-ORD

14h 02m1 stop

$112Spirit Airlines

Find Deal

mié., ago. 27 - mié., sep. 3

7:30 am - 11:01 amORD-BOS

2h 31mnonstop

4:27 pm - 6:21 pmBOS-ORD

2h 54mnonstop

$117United Airlines

Find Deal

mié., sep. 3 - mié., sep. 3

7:10 pm - 10:40 pmORD-BOS

2h 30mnonstop

8:35 am - 10:32 amBOS-ORD

2h 57mnonstop

$120American Airlines

Find Deal

mié., sep. 3 - jue., sep. 4

6:45 am - 10:00 amMDW-BOS

2h 15mnonstop

5:30 am - 7:05 amBOS-MDW

2h 35mnonstop

$127Southwest

Find Deal

jue., sep. 4 - dom., sep. 7

8:25 pm - 11:53 pmORD-BOS

2h 28mnonstop

7:01 am - 9:05 amBOS-ORD

3h 04mnonstop

$128American Airlines

Find Deal

jue., sep. 4 - dom., sep. 7

11:30 am - 2:46 pmORD-BOS

2h 16mnonstop

4:55 pm - 7:05 pmBOS-ORD

3h 10mnonstop

$132JetBlue

Find Deal

mar., oct. 28 - mar., oct. 28

7:50 pm - 11:25 pmORD-BOS

2h 35mnonstop

7:00 am - 8:56 amBOS-ORD

2h 56mnonstop

$137JetBlue

Find Deal

vie., sep. 19 - lun., sep. 22

2:35 pm - 11:00 pmMDW-BOS

7h 25m1 stop

5:40 pm - 7:20 pmBOS-MDW

2h 40mnonstop

$137Southwest

Find Deal

jue., sep. 4 - mié., sep. 10

10:15 am - 1:48 pmORD-BOS

2h 33mnonstop

7:55 pm - 9:56 pmBOS-ORD

3h 01mnonstop

$147Delta

Find Deal

jue., sep. 4 - mié., sep. 10

7:25 am - 10:55 amORD-BOS

2h 30mnonstop

7:20 am - 9:22 amBOS-ORD

3h 02mnonstop

$150Delta

Find Deal

mar., sep. 30 - mié., oct. 8

JetBlue flights from Illinois to Massachusetts

Our best JetBlue deals on Illinois to Massachusetts flight tickets

JetBlue

Oct 28

ORD11:30 amChicago O'Hare Intl

2h 16m

BOS2:46 pmBoston Logan Intl

Oct 28

BOS4:55 pmBoston Logan Intl

3h 10m

ORD7:05 pmChicago O'Hare Intl

$132

Find similar

JetBlue

Sep 19

ORD7:50 pmChicago O'Hare Intl

2h 35m

BOS11:25 pmBoston Logan Intl

Sep 22

BOS7:00 amBoston Logan Intl

2h 56m

ORD8:56 amChicago O'Hare Intl

$137

Find similar

JetBlue

Oct 24

ORD9:42 amChicago O'Hare Intl

2h 28m

BOS1:10 pmBoston Logan Intl

Oct 27

BOS8:30 amBoston Logan Intl

2h 58m

ORD10:28 amChicago O'Hare Intl

$140

Find similar

Frontier flights from Illinois to Massachusetts

Our best Frontier deals on Illinois to Massachusetts flight tickets

Frontier

Aug 9

ORD12:20 pmChicago O'Hare Intl

11h 19m

1 stop

BOS12:39 amBoston Logan Intl

Aug 16

BOS6:00 amBoston Logan Intl

14h 12m

1 stop

ORD7:12 pmChicago O'Hare Intl

$198

Find similar

Frontier

Aug 14

MDW9:12 pmChicago Midway

10h 23m

1 stop

BOS8:35 amBoston Logan Intl

Aug 16

BOS9:40 amBoston Logan Intl

11h 42m

1 stop

MDW8:22 pmChicago Midway

$208

Find similar

Frontier

Sep 26

MDW6:21 amChicago Midway

24h 50m

1 stop

BOS8:11 amBoston Logan Intl

Oct 4

BOS8:56 amBoston Logan Intl

28h 48m

1 stop

MDW12:44 pmChicago Midway

$209

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mié. 8/27

11:36 am-11:49 pm

1 stop11h 13m

Boston Logan Intl

mié. 9/3

6:05 am-7:07 pm

1 stop14h 02m

$112

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mié. 9/3

7:30 am-11:01 am

Nonstop2h 31m

Boston Logan Intl

mié. 9/3

4:27 pm-6:21 pm

Nonstop2h 54m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mié. 9/3

7:10 pm-10:40 pm

Nonstop2h 30m

Boston Logan Intl

jue. 9/4

8:35 am-10:32 am

Nonstop2h 57m

$120

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

jue. 9/4

6:45 am-10:00 am

Nonstop2h 15m

Boston Logan Intl

dom. 9/7

5:30 am-7:05 am

Nonstop2h 35m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 9/4

8:25 pm-11:53 pm

Nonstop2h 28m

Boston Logan Intl

dom. 9/7

7:01 am-9:05 am

Nonstop3h 04m

$128

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mar. 10/28

11:30 am-2:46 pm

Nonstop2h 16m

Boston Logan Intl

mar. 10/28

4:55 pm-7:05 pm

Nonstop3h 10m

$132

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

vie. 9/19

7:50 pm-11:25 pm

Nonstop2h 35m

Boston Logan Intl

lun. 9/22

7:00 am-8:56 am

Nonstop2h 56m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

jue. 9/4

2:35 pm-11:00 pm

1 stop7h 25m

Boston Logan Intl

mié. 9/10

5:40 pm-7:20 pm

Nonstop2h 40m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 9/4

10:15 am-1:48 pm

Nonstop2h 33m

Boston Logan Intl

mié. 9/10

7:55 pm-9:56 pm

Nonstop3h 01m

$147

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mar. 9/30

7:25 am-10:55 am

Nonstop2h 30m

Boston Logan Intl

mié. 10/8

7:20 am-9:22 am

Nonstop3h 02m

$150

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 $189. If you aren’t able to travel to Massachusetts during the month of September, then flying in August 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 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 $238. 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, Sunday 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 $303.

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 $212. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are $284 on average. Flights to Massachusetts from Illinois in the afternoon 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 $229 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 $192 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	$55
Fastest flight time	1h 50m
Direct flights	Every day
Airports in Massachusetts	3 airports

The best one-way flight to Massachusetts from Illinois in the past 72 hours is $55. The best round-trip flight deal from Illinois to Massachusetts found on momondo in the last 72 hours is $112.

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

Direct flights go from Illinois to Massachusetts every day.

There are 3 airports near Massachusetts: Boston Logan Intl (BOS), 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 July 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 23.02% of the total bookings. Other popular models include Embraer 175 with 11.33%, Airbus A220-300 with 10.89%, and Boeing 737 MAX 8 with 10.60%.

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 $35	Free Cancellation	Rating 6.3 8,049 reviews	Search Spirit Airlines flights
JetBlue	PriceFrom $78	Free Cancellation	Rating 7.2 2,914 reviews	Search JetBlue flights
Delta	PriceFrom $90	Free Cancellation	Rating 8.0 7,981 reviews	Search Delta flights
Frontier	PriceFrom $100	Free Cancellation	Rating 5.9 3,239 reviews	Search Frontier flights
American Airlines	PriceFrom $122	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $131	Free Cancellation	Rating 7.4 8,900 reviews	Search United Airlines flights
Southwest	PriceFrom $153	Free Cancellation	Rating 8.0 4,246 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 $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 Illinois to Massachusetts 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.

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 Illinois to Massachusetts

Cheap round-trip flights

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Cheap last minute flights

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JetBlue flights from Illinois to Massachusetts

Our best JetBlue deals on Illinois to Massachusetts flight tickets

Frontier flights from Illinois to Massachusetts

Our best Frontier 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 Midway 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?

Spirit Airlines, JetBlue, and Southwest 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 July 2025, 87 flights take off from Illinois and land in Massachusetts each day. The most common flight departure time for this route is 8:00AM, with 42% of daily flights taking off at noon.

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

As of July 2025, there are 610 flights per week flying from Illinois to Massachusetts. The most common day of the week flights depart is Thu, with 23% 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 Peoria and into Boston, then the flight time is around 5h.

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