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

762 flights are operational weekly from Massachusetts to Chicago as of September 2025. The most popular departure day for this route is Mon, with 17% of flights per week taking off on this day.

How long does it take to fly to Chicago?

Average flight duration from Massachusetts to Chicago depends on which airport you fly into and out of. Flying from Boston to Chicago O'Hare Intl Airport is 2h 48m on average, while flying from West Tisbury to Chicago O'Hare Intl Airport is 4h 40m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

What airlines fly to Chicago?

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Chicago from Massachusetts 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 Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

Southwest, United Airlines, and JetBlue are the most popular carriers operating from Massachusetts to Chicago

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

108 flights are operational daily from Massachusetts to Chicago as of September 2025. The most popular departure time for this route is 7:00AM, with 44% of flights per day taking off at noon.

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

Prices for flights from Massachusetts to Chicago are updated daily.

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

There are 7 operators available for flights from Massachusetts to Chicago as of September 2025.

How old do you have to be to fly from Massachusetts to Chicago?

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 Chicago.

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

The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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

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Find the cheapest flights from Massachusetts to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

5:35 pm - 9:05 pmBOS-MDW

4h 30m1 stop

7:15 pm - 10:30 pmMDW-BOS

2h 15mnonstop

$123Southwest

Find Deal

Tue, Nov 11 - Fri, Nov 14

6:16 am - 6:38 pmBOS-ORD

13h 22m1 stop

6:00 am - 1:20 pmORD-BOS

6h 20m1 stop

$126Spirit Airlines

Find Deal

Tue, Oct 7 - Wed, Oct 15

6:15 pm - 8:10 pmBOS-ORD

2h 55mnonstop

11:05 am - 2:40 pmORD-BOS

2h 35mnonstop

$127United Airlines

Find Deal

Tue, Sep 30 - Wed, Oct 1

4:02 pm - 6:24 pmBOS-ORD

3h 22mnonstop

6:35 pm - 10:05 pmORD-BOS

2h 30mnonstop

$128American Airlines

Find Deal

Wed, Nov 12 - Wed, Nov 26

7:29 pm - 9:23 pmBOS-ORD

2h 54mnonstop

7:10 am - 10:29 amORD-BOS

2h 19mnonstop

$129American Airlines

Find Deal

Tue, Sep 30 - Wed, Oct 1

8:38 am - 4:45 pmBOS-ORD

9h 07m1 stop

6:00 am - 1:20 pmORD-BOS

6h 20m1 stop

$131Multiple Airlines

Find Deal

Sat, Oct 4 - Tue, Oct 7

4:40 pm - 6:55 pmBOS-ORD

3h 15mnonstop

9:51 am - 1:20 pmORD-BOS

2h 29mnonstop

$132JetBlue

Find Deal

Fri, Sep 26 - Wed, Oct 1

6:15 pm - 8:09 pmBOS-ORD

2h 54mnonstop

6:30 am - 9:56 amORD-BOS

2h 26mnonstop

$133United Airlines

Find Deal

Sat, Oct 18 - Sun, Oct 19

7:09 am - 9:22 amBOS-ORD

3h 13mnonstop

10:08 am - 1:37 pmORD-BOS

2h 29mnonstop

$135JetBlue

Find Deal

Wed, Oct 15 - Wed, Oct 22

8:47 am - 4:51 pmBOS-ORD

9h 04m1 stop

11:57 am - 11:57 pmORD-BOS

11h 00m1 stop

$159Multiple Airlines

Find Deal

Thu, Oct 2 - Sat, Oct 4

Delta flights from Massachusetts to Chicago

Our best Delta deals on Massachusetts to Chicago flight tickets

Delta

Oct 15

BOS7:20 amBoston Logan Intl

3h 02m

ORD9:22 amChicago O'Hare Intl

Oct 22

ORD10:25 amChicago O'Hare Intl

2h 30m

BOS1:55 pmBoston Logan Intl

$147

Find similar

Delta

Nov 20

BOS12:45 pmBoston Logan Intl

3h 02m

ORD2:47 pmChicago O'Hare Intl

Nov 24

ORD7:10 amChicago O'Hare Intl

2h 26m

BOS10:36 amBoston Logan Intl

$157

Find similar

Delta

Sep 30

BOS4:05 pmBoston Logan Intl

2h 54m

ORD5:59 pmChicago O'Hare Intl

Oct 1

ORD7:25 amChicago O'Hare Intl

2h 30m

BOS10:55 amBoston Logan Intl

$177

Find similar

JetBlue flights from Massachusetts to Chicago

Our best JetBlue deals on Massachusetts to Chicago flight tickets

JetBlue

Sep 26

BOS4:40 pmBoston Logan Intl

3h 15m

ORD6:55 pmChicago O'Hare Intl

Oct 1

ORD9:51 amChicago O'Hare Intl

2h 29m

BOS1:20 pmBoston Logan Intl

$132

Find similar

JetBlue

Oct 15

BOS7:09 amBoston Logan Intl

3h 13m

ORD9:22 amChicago O'Hare Intl

Oct 22

ORD10:08 amChicago O'Hare Intl

2h 29m

BOS1:37 pmBoston Logan Intl

$135

Find similar

JetBlue

Sep 25

BOS7:00 amBoston Logan Intl

2h 56m

ORD8:56 amChicago O'Hare Intl

Sep 27

ORD9:51 amChicago O'Hare Intl

2h 29m

BOS1:20 pmBoston Logan Intl

$137

Find similar

Fly from

Fly to

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 11/11

5:35 pm-9:05 pm

1 stop4h 30m

Chicago Midway

Fri 11/14

7:15 pm-10:30 pm

Nonstop2h 15m

$123

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 10/7

6:16 am-6:38 pm

1 stop13h 22m

Chicago O'Hare Intl

Wed 10/15

6:00 am-1:20 pm

1 stop6h 20m

$126

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 9/30

6:15 pm-8:10 pm

Nonstop2h 55m

Chicago O'Hare Intl

Wed 10/1

11:05 am-2:40 pm

Nonstop2h 35m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 11/12

4:02 pm-6:24 pm

Nonstop3h 22m

Chicago O'Hare Intl

Wed 11/26

6:35 pm-10:05 pm

Nonstop2h 30m

$128

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 9/30

7:29 pm-9:23 pm

Nonstop2h 54m

Chicago O'Hare Intl

Wed 10/1

7:10 am-10:29 am

Nonstop2h 19m

$129

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 10/4

8:38 am-4:45 pm

1 stop9h 07m

Chicago O'Hare Intl

Tue 10/7

6:00 am-1:20 pm

1 stop6h 20m

$131

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 9/26

4:40 pm-6:55 pm

Nonstop3h 15m

Chicago O'Hare Intl

Wed 10/1

9:51 am-1:20 pm

Nonstop2h 29m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 10/18

6:15 pm-8:09 pm

Nonstop2h 54m

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 10/22

10:08 am-1:37 pm

Nonstop2h 29m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 10/2

8:47 am-4:51 pm

1 stop9h 04m

Chicago O'Hare Intl

Sat 10/4

11:57 am-11:57 pm

1 stop11h 00m

$159

Flights are sorted by cheapest round-trip flights first.

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How to get the cheapest flight ticket from Massachusetts to Chicago

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 Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Massachusetts, with most prices found around $196. If you’re not able to fly to Chicago in January, then September is your next best option. Flight prices from Massachusetts to Chicago during September average around $199.

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

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $321. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Massachusetts to Chicago for around $426.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Massachusetts to Chicago during this time can be as low as $275. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $351.

What is the cheapest Massachusetts to Chicago flight route?

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

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

You are more likely to see cheaper flights to Chicago from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $250 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Massachusetts for as low as $217 on momondo.

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

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

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

Cheap Massachusetts to Chicago flight deals and tips

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

Best Price Found	$106
Fastest flight time	2h 10m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from Massachusetts in the past 72 hours is $106. The best round-trip flight deal from Massachusetts to Chicago found on momondo in the last 72 hours is $203.

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

Direct flights go from Massachusetts to Chicago every day.

There is 1 airport near Chicago: Chicago Midway (MDW)

Search flight deals

When did momondo last update prices for flights from Massachusetts to Chicago?
Prices for flights from Massachusetts to Chicago are updated daily.
How many operators does momondo search for flights from Massachusetts to Chicago?
There are 7 operators available for flights from Massachusetts to Chicago as of September 2025.
How old do you have to be to fly from Massachusetts to Chicago?
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 Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Massachusetts to Chicago?
Based on momondo bookings for flights between Massachusetts and Chicago, the leading plane model is Boeing 737-800, making up 26.57% of the total bookings. Other popular models include Boeing 737 MAX 8 with 13.75%, Boeing 737-900 with 11.40%, and Airbus A220-300 with 10.27%.

Best airlines flying from Massachusetts to Chicago

Compare and see reviews for airlines that fly from Massachusetts to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $50	Free Cancellation	Rating 6.3 8,023 reviews	Search Spirit Airlines flights
JetBlue	PriceFrom $83	Free Cancellation	Rating 7.2 2,914 reviews	Search JetBlue flights
United Airlines	PriceFrom $97	Free Cancellation	Rating 7.4 8,926 reviews	Search United Airlines flights
Frontier	PriceFrom $100	Free Cancellation	Rating 5.8 3,173 reviews	Search Frontier flights
Delta	PriceFrom $107	Free Cancellation	Rating 7.9 7,961 reviews	Search Delta flights
Southwest	PriceFrom $120	Free Cancellation	Rating 8.0 4,242 reviews	Search Southwest flights
American Airlines	PriceFrom $137	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights

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Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

It is quick and easy to find Massachusetts to Chicago 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 Chicago that suits you.

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

momondo does allow users to show only those flights to Chicago 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 Chicago?

Once all potential Massachusetts to Chicago 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 Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Massachusetts to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Cheap flights from Massachusetts to Chicago 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 Chicago departing on 11/4. 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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Big names and deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Massachusetts to Chicago

Cheap round-trip flights

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Cheap last minute flights

Cheap direct flights

Delta flights from Massachusetts to Chicago

Our best Delta deals on Massachusetts to Chicago flight tickets

JetBlue flights from Massachusetts to Chicago

Our best JetBlue deals on Massachusetts to Chicago flight tickets

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

See travel insights to Chicago from

How to get the cheapest flight ticket from Massachusetts to Chicago

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 Chicago?

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

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Massachusetts to Chicago during this time can be as low as $275. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $351.

What is the cheapest Massachusetts to Chicago flight route?

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

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

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

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

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

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

Southwest, United Airlines, and JetBlue are the most popular carriers operating from Massachusetts to Chicago

What airlines fly to Chicago?

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

108 flights are operational daily from Massachusetts to Chicago as of September 2025. The most popular departure time for this route is 7:00AM, with 44% of flights per day taking off at noon.

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

762 flights are operational weekly from Massachusetts to Chicago as of September 2025. The most popular departure day for this route is Mon, with 17% of flights per week taking off on this day.

How long does it take to fly to Chicago?

Cheap Massachusetts to Chicago flight deals and tips

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

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

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

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

How old do you have to be to fly from Massachusetts to Chicago?

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

What is the most popular plane model from Massachusetts to Chicago?

Best airlines flying from Massachusetts to Chicago

Compare and see reviews for airlines that fly from Massachusetts to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago 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 the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago