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

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

What airlines fly to Chicago?

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Chicago from Massachusetts according to our data. United 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 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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 50m on average, while flying from Worcester to Chicago O'Hare Intl Airport is 5h 45m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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

46 flights are operational daily from Massachusetts to Chicago as of November 2026. The most popular departure time for this route is 7:00AM, with 42% of flights per day taking off in the afternoon.

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

324 flights are operational weekly from Massachusetts to Chicago as of November 2026. The most popular departure day for this route is Mon, with 21% of flights per week taking off on this day.

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 5 operators available for flights from Massachusetts to Chicago as of November 2026.

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.

$115 Cheap Flights from Massachusetts to Chicago in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Massachusetts to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:35 am - 4:26 pmBOS Boston Logan Intl-MDW Chicago Midway

7h 51m1 stop Atlanta Hartsfield-Jackson

8:47 pm - 9:29 amMDW Chicago Midway-BOS Boston Logan Intl

11h 42m1 stop Orlando

$217Frontier

Sat, Jan 9 - Mon, Jan 18

9:35 am - 4:26 pmBOS Boston Logan Intl-MDW Chicago Midway

7h 51m1 stop Atlanta Hartsfield-Jackson

8:47 pm - 9:29 amMDW Chicago Midway-BOS Boston Logan Intl

11h 42m1 stop Orlando

$217Frontier

Sat, Jan 9 - Fri, Jan 15

2:40 pm - 4:42 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

5:46 pm - 9:14 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 28mnonstop

$245JetBlue

Mon, Dec 7 - Tue, Dec 8

2:40 pm - 4:42 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

5:46 pm - 9:14 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 28mnonstop

$245JetBlue

Tue, Dec 8 - Thu, Dec 10

8:25 am - 10:40 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 15mnonstop

10:46 am - 2:20 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 34mnonstop

$247American Airlines

Tue, Jan 19 - Thu, Jan 21

8:19 am - 10:35 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 16mnonstop

7:15 pm - 10:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 44mnonstop

$247American Airlines

Tue, Dec 15 - Tue, Jan 5

7:30 am - 9:38 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 08mnonstop

7:45 pm - 11:17 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 32mnonstop

$247Delta

Tue, Dec 1 - Tue, Dec 1

4:35 pm - 6:45 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 10mnonstop

7:45 pm - 11:17 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 32mnonstop

$247Delta

Tue, Dec 1 - Thu, Dec 3

1:24 pm - 3:26 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

10:30 am - 1:55 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 25mnonstop

$247United Airlines

Thu, Jan 14 - Tue, Jan 19

7:31 am - 9:34 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 03mnonstop

9:10 am - 12:43 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 33mnonstop

$247United Airlines

Thu, Nov 26 - Wed, Dec 2

Cheap last minute flights

Enter your travel dates to find the best prices.

12:39 pm - 11:47 pmBOS Boston Logan Intl-MDW Chicago Midway

12h 08m1 stop Atlanta Hartsfield-Jackson

8:42 pm - 10:11 amMDW Chicago Midway-BOS Boston Logan Intl

12h 29m1 stop Orlando

$259Frontier

Mon, Nov 9 - Sat, Nov 21

11:27 am - 6:30 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

8h 03m1 stop Atlanta Hartsfield-Jackson

5:24 pm - 10:13 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

15h 49m1 stop Orlando

$278Frontier

Sat, Nov 7 - Sat, Dec 5

7:30 am - 9:35 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 05mnonstop

7:45 pm - 11:08 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 23mnonstop

$324Delta

Mon, Nov 9 - Mon, Nov 16

6:00 am - 8:00 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 00mnonstop

7:00 am - 10:19 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 19mnonstop

$324United Airlines

Mon, Nov 9 - Thu, Nov 12

4:56 pm - 6:58 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

9:13 am - 12:46 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 33mnonstop

$324United Airlines

Sat, Nov 7 - Thu, Nov 12

11:35 am - 4:30 pmBOS Boston Logan Intl-MDW Chicago Midway

5h 55m1 stop Baltimore/Washington

6:45 pm - 10:05 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

$342Southwest

Sat, Nov 7 - Thu, Nov 12

5:05 pm - 7:17 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 12mnonstop

8:15 pm - 11:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 44mnonstop

$346JetBlue

Mon, Nov 9 - Fri, Nov 13

8:40 pm - 10:36 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

7:05 am - 10:32 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 27mnonstop

$347Delta

Mon, Nov 9 - Sun, Nov 15

4:20 pm - 6:05 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 45mnonstop

3:35 pm - 6:50 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 15mnonstop

$347Southwest

Mon, Nov 9 - Sun, Nov 15

9:59 am - 12:00 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 01mnonstop

5:46 pm - 9:14 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 28mnonstop

$356JetBlue

Mon, Nov 9 - Sat, Dec 5

Cheap direct flights

Enter your travel dates to find the best prices.

2:40 pm - 4:42 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

5:46 pm - 9:14 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 28mnonstop

$245JetBlue

Mon, Dec 7 - Tue, Dec 8

2:40 pm - 4:42 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

5:46 pm - 9:14 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 28mnonstop

$245JetBlue

Tue, Dec 8 - Thu, Dec 10

8:25 am - 10:40 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 15mnonstop

10:46 am - 2:20 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 34mnonstop

$247American Airlines

Tue, Jan 19 - Thu, Jan 21

8:19 am - 10:35 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 16mnonstop

7:15 pm - 10:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 44mnonstop

$247American Airlines

Tue, Dec 15 - Tue, Jan 5

7:30 am - 9:38 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 08mnonstop

7:45 pm - 11:17 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 32mnonstop

$247Delta

Tue, Dec 1 - Tue, Dec 1

4:35 pm - 6:45 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 10mnonstop

7:45 pm - 11:17 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 32mnonstop

$247Delta

Tue, Dec 1 - Thu, Dec 3

1:24 pm - 3:26 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

10:30 am - 1:55 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 25mnonstop

$247United Airlines

Thu, Jan 14 - Tue, Jan 19

7:31 am - 9:34 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 03mnonstop

9:10 am - 12:43 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 33mnonstop

$247United Airlines

Thu, Nov 26 - Wed, Dec 2

7:25 am - 9:15 amBOS Boston Logan Intl-MDW Chicago Midway

2h 50mnonstop

8:20 am - 11:45 amMDW Chicago Midway-BOS Boston Logan Intl

2h 25mnonstop

$247Southwest

Thu, Jan 14 - Tue, Jan 19

7:10 am - 8:55 amBOS Boston Logan Intl-MDW Chicago Midway

2h 45mnonstop

6:25 pm - 9:45 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

$247Southwest

Tue, Dec 1 - Thu, Dec 3

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Delta flights from Massachusetts to Chicago

Our best Delta deals on Massachusetts to Chicago flight tickets

Delta

Jan 16

BOS2:30 pmBoston Logan Intl

3h 06m

ORD4:36 pmChicago O'Hare Intl

Jan 23

ORD10:18 amChicago O'Hare Intl

2h 27m

BOS1:45 pmBoston Logan Intl

$247

Delta

Nov 19

BOS8:40 pmBoston Logan Intl

2h 56m

ORD10:36 pmChicago O'Hare Intl

Dec 1

ORD10:38 amChicago O'Hare Intl

2h 37m

BOS2:15 pmBoston Logan Intl

$267

Delta

Nov 18

BOS8:40 pmBoston Logan Intl

2h 56m

ORD10:36 pmChicago O'Hare Intl

Dec 1

ORD7:45 pmChicago O'Hare Intl

2h 32m

BOS11:17 pmBoston Logan Intl

$268

Frontier flights from Massachusetts to Chicago

Our best Frontier deals on Massachusetts to Chicago flight tickets

Frontier

Jan 9

BOS9:35 amBoston Logan Intl

7h 51m

1 stop

MDW4:26 pmChicago Midway

Jan 18

MDW8:47 pmChicago Midway

11h 42m

1 stop

BOS9:29 amBoston Logan Intl

$217

Frontier

Nov 14

BOS11:27 amBoston Logan Intl

8h 03m

1 stop

ORD6:30 pmChicago O'Hare Intl

Dec 2

ORD5:35 amChicago O'Hare Intl

27h 36m

1 stop

BOS10:11 amBoston Logan Intl

$218

Frontier

Nov 26

BOS11:06 amBoston Logan Intl

14h 36m

1 stop

ORD12:42 amChicago O'Hare Intl

Dec 2

ORD5:35 amChicago O'Hare Intl

27h 36m

1 stop

BOS10:11 amBoston Logan Intl

$222

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Sat 1/9

9:35 am-4:26 pm

1 stop7h 51m

Chicago Midway

Mon 1/18

8:47 pm-9:29 am

1 stop11h 42m

$217

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Sat 1/9

9:35 am-4:26 pm

1 stop7h 51m

Chicago Midway

Fri 1/15

8:47 pm-9:29 am

1 stop11h 42m

$217

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Mon 12/7

2:40 pm-4:42 pm

Nonstop3h 02m

Chicago O'Hare Intl

Tue 12/8

5:46 pm-9:14 pm

Nonstop2h 28m

$245

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Tue 12/8

2:40 pm-4:42 pm

Nonstop3h 02m

Chicago O'Hare Intl

Thu 12/10

5:46 pm-9:14 pm

Nonstop2h 28m

$245

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Tue 1/19

8:25 am-10:40 am

Nonstop3h 15m

Chicago O'Hare Intl

Thu 1/21

10:46 am-2:20 pm

Nonstop2h 34m

$247

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Tue 12/15

8:19 am-10:35 am

Nonstop3h 16m

Chicago O'Hare Intl

Tue 1/5

7:15 pm-10:59 pm

Nonstop2h 44m

$247

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Tue 12/1

7:30 am-9:38 am

Nonstop3h 08m

Chicago O'Hare Intl

Tue 12/1

7:45 pm-11:17 pm

Nonstop2h 32m

$247

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Tue 12/1

4:35 pm-6:45 pm

Nonstop3h 10m

Chicago O'Hare Intl

Thu 12/3

7:45 pm-11:17 pm

Nonstop2h 32m

$247

Quickest round-trip

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Thu 1/14

1:24 pm-3:26 pm

Nonstop3h 02m

Chicago O'Hare Intl

Tue 1/19

10:30 am-1:55 pm

Nonstop2h 25m

$247

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Thu 11/26

7:31 am-9:34 am

Nonstop3h 03m

Chicago O'Hare Intl

Wed 12/2

9:10 am-12:43 pm

Nonstop2h 33m

$247

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 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 $200. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from Massachusetts to Chicago during February average around $220.

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 $336. 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 $429.

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 $307. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $371.

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 from Massachusetts 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 $278 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 $241 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	$115
Fastest flight time	2h 15m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Massachusetts in the past 72 hours is $115. The best round-trip flight deal from Massachusetts to Chicago found on momondo in the last 72 hours is $217.

The fastest flight from Massachusetts to Chicago takes 2h 15m

Direct flights go from Massachusetts to Chicago every day.

There are 3 airports in Chicago. From Massachusetts there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).

Search flight deals

Frequently asked questions about flying from Massachusetts to Chicago

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 5 operators available for flights from Massachusetts to Chicago as of November 2026.
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 19.05% of the total bookings. Other popular models include Boeing 737 MAX 8 with 12.21%, Airbus A321neo with 11.66%, and Airbus A220-300 with 9.44%.

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
JetBlue	PriceFrom $79	Free Cancellation	Rating 7.1 3,065 reviews	Search JetBlue flights
Delta	PriceFrom $88	Free Cancellation	Rating 7.8 8,699 reviews	Search Delta flights
United Airlines	PriceFrom $136	Free Cancellation	Rating 7.3 10,460 reviews	Search United Airlines flights
American Airlines	PriceFrom $153	Free Cancellation	Rating 7.0 12,228 reviews	Search American Airlines flights
Southwest	PriceFrom $157	Free Cancellation	Rating 8.0 4,215 reviews	Search Southwest flights

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Hammond

Portage

Lansing

Saint Joseph

Benton Harbor

Valparaiso

Schererville

Munster

Chesterton

Monticello

Crown Point

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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Other United States destinations

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Complete your trip

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Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Cheap flights from Massachusetts to Chicago from $115

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 12/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Find the cheapest flights from Massachusetts to Chicago

Cheap round-trip flights

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Cheap last minute flights

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Big names and deals

Big names and deals

Filter for what you want

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Delta flights from Massachusetts to Chicago

Our best Delta deals on Massachusetts to Chicago flight tickets

Frontier flights from Massachusetts to Chicago

Our best Frontier deals on Massachusetts to Chicago flight tickets

momondo Fare Finder

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

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?

What is the cheapest Massachusetts to Chicago flight route?

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

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

Can stopping save me money on Massachusetts to Chicago flights?

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

What airlines fly to Chicago?

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

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

How long does it take to fly to Chicago?

Cheap Massachusetts to Chicago flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying 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?

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

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

Popular cities in the United States

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

Fly to other destinations from Massachusetts

According to popular flight searches on momondo this year

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Explore popular destinations other users love

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