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 52m on average, while flying from Worcester to Chicago O'Hare Intl Airport is 5h 33m on average. Chicago O'Hare Intl Airport is the most popular airport in 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 many flights depart from Massachusetts to Chicago on average per week?

343 flights are operational weekly from Massachusetts to Chicago as of September 2026. The most popular departure day for this route is Mon, with 22% of flights per week taking off on this day.

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

49 flights are operational daily from Massachusetts to Chicago as of September 2026. The most popular departure time for this route is 7:00AM, with 47% of flights per day taking off in the afternoon.

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

Delta, United Airlines, and JetBlue are the most popular carriers operating 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 September 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.

$100 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.

5:16 pm - 10:30 pmORH Worcester-ORD Chicago O'Hare Intl

6h 14m1 stop Philadelphia

8:29 am - 4:49 pmORD Chicago O'Hare Intl-ORH Worcester

7h 20m1 stop Philadelphia

$204American Airlines

Wed, Oct 14 - Wed, Oct 21

4:15 pm - 10:17 pmORH Worcester-ORD Chicago O'Hare Intl

7h 02m1 stop New York LaGuardia

7:00 am - 2:58 pmORD Chicago O'Hare Intl-ORH Worcester

6h 58m1 stop New York LaGuardia

$204Delta

Tue, Oct 13 - Tue, Oct 20

4:15 pm - 8:43 pmORH Worcester-ORD Chicago O'Hare Intl

5h 28m1 stop New York LaGuardia

8:36 am - 2:58 pmORD Chicago O'Hare Intl-ORH Worcester

5h 22m1 stop New York LaGuardia

$204Delta

Tue, Oct 13 - Wed, Oct 21

6:55 am - 8:47 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

6:10 am - 2:29 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

7h 19m1 stop New York John F Kennedy Intl

$212JetBlue

Thu, Oct 15 - Tue, Oct 20

6:55 am - 8:47 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

6:10 am - 2:29 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

7h 19m1 stop New York John F Kennedy Intl

$212JetBlue

Tue, Oct 13 - Mon, Oct 19

11:55 am - 1:59 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 04mnonstop

6:59 am - 12:26 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

4h 27m1 stop Newark

$212United Airlines

Wed, Oct 28 - Thu, Oct 29

11:55 am - 1:59 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 04mnonstop

7:00 am - 12:26 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

4h 26m1 stop Newark

$212United Airlines

Thu, Nov 5 - Wed, Nov 11

10:00 pm - 11:40 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 40mnonstop

8:10 am - 2:55 pmMDW Chicago Midway-BOS Boston Logan Intl

5h 45m1 stop Baltimore/Washington

$212Southwest

Thu, Oct 15 - Tue, Oct 20

11:45 am - 5:10 pmBOS Boston Logan Intl-MDW Chicago Midway

6h 25m1 stop Lambert-St Louis

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

2h 20mnonstop

$212Southwest

Tue, Oct 27 - Thu, Oct 29

7:00 am - 9:05 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 05mnonstop

8:00 pm - 11:36 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 36mnonstop

$214American Airlines

Sat, Oct 17 - Thu, Oct 22

Cheap last minute flights

Enter your travel dates to find the best prices.

4:10 pm - 10:00 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 50m1 stop New York John F Kennedy Intl

5:30 pm - 8:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 29mnonstop

$232JetBlue

Mon, Oct 5 - Mon, Nov 30

4:11 pm - 9:59 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 48m1 stop New York John F Kennedy Intl

8:00 pm - 11:58 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 58mnonstop

$237JetBlue

Fri, Oct 2 - Mon, Oct 12

12:54 pm - 6:23 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 29m1 stop Atlanta Hartsfield-Jackson

1:00 pm - 4:48 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 48mnonstop

$254Multiple Airlines

Thu, Oct 1 - Wed, Nov 4

12:54 pm - 6:23 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 29m1 stop Atlanta Hartsfield-Jackson

8:04 pm - 11:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 55mnonstop

$254Multiple Airlines

Thu, Oct 1 - Tue, Oct 20

5:16 pm - 10:56 amORH Worcester-ORD Chicago O'Hare Intl

18h 40m1 stop Philadelphia

6:29 am - 4:49 pmORD Chicago O'Hare Intl-ORH Worcester

9h 20m1 stop Philadelphia

$286American Airlines

Sat, Oct 3 - Sat, Oct 10

4:29 pm - 6:42 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 13mnonstop

7:13 pm - 10:42 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 29mnonstop

$303American Airlines

Thu, Oct 1 - Wed, Nov 4

6:35 pm - 8:10 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

7:50 am - 11:10 amMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

$303Southwest

Thu, Oct 1 - Tue, Oct 20

7:05 am - 8:40 amBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

7:15 pm - 10:30 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 15mnonstop

$303Southwest

Thu, Oct 1 - Wed, Nov 4

7:30 am - 9:24 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

7:10 pm - 10:53 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 43mnonstop

$303Delta

Mon, Oct 5 - Tue, Oct 13

8:50 pm - 10:32 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 42mnonstop

10:24 am - 1:54 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 30mnonstop

$303Delta

Mon, Oct 5 - Wed, Oct 14

Cheap direct flights

Enter your travel dates to find the best prices.

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

3h 12mnonstop

1:00 pm - 4:49 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 49mnonstop

$213JetBlue

Thu, Nov 5 - Tue, Nov 10

6:55 am - 8:47 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

8:04 pm - 11:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 55mnonstop

$213JetBlue

Wed, Oct 21 - Sat, Oct 24

7:00 am - 9:05 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 05mnonstop

8:00 pm - 11:36 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 36mnonstop

$214American Airlines

Sat, Oct 17 - Thu, Oct 22

8:23 am - 10:30 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 07mnonstop

7:03 pm - 10:37 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 34mnonstop

$215American Airlines

Thu, Oct 15 - Mon, Oct 19

7:01 am - 9:00 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

9:24 pm - 12:54 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 30mnonstop

$215United Airlines

Sat, Oct 17 - Thu, Oct 22

12:45 pm - 2:37 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

1:59 pm - 5:24 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 25mnonstop

$215United Airlines

Sat, Oct 24 - Sat, Oct 31

10:00 pm - 11:40 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 40mnonstop

5:30 am - 8:55 amMDW Chicago Midway-BOS Boston Logan Intl

2h 25mnonstop

$215Southwest

Thu, Oct 15 - Mon, Oct 19

5:50 am - 7:25 amBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

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

2h 20mnonstop

$215Southwest

Thu, Oct 29 - Thu, Oct 29

1:35 pm - 3:27 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

10:24 am - 1:54 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 30mnonstop

$222Delta

Sat, Oct 24 - Tue, Oct 27

7:50 am - 9:48 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 58mnonstop

7:25 am - 11:00 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

$222Delta

Sat, Oct 31 - Wed, Nov 4

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Delta flights from Massachusetts to Chicago

Our best Delta deals on Massachusetts to Chicago flight tickets

Delta

Oct 13

ORH4:15 pmWorcester

7h 02m

1 stop

ORD10:17 pmChicago O'Hare Intl

Oct 20

ORD7:00 amChicago O'Hare Intl

6h 58m

1 stop

ORH2:58 pmWorcester

$204

Delta

Oct 13

ORH4:15 pmWorcester

5h 28m

1 stop

ORD8:43 pmChicago O'Hare Intl

Oct 21

ORD7:00 amChicago O'Hare Intl

6h 58m

2 stops

ORH2:58 pmWorcester

$214

Delta

Oct 12

ORH4:15 pmWorcester

7h 02m

1 stop

ORD10:17 pmChicago O'Hare Intl

Oct 20

ORD8:36 amChicago O'Hare Intl

5h 22m

1 stop

ORH2:58 pmWorcester

$217

JetBlue flights from Massachusetts to Chicago

Our best JetBlue deals on Massachusetts to Chicago flight tickets

JetBlue

Oct 13

BOS6:55 amBoston Logan Intl

5h 29m

1 stop

ORD11:24 amChicago O'Hare Intl

Oct 19

ORD6:10 amChicago O'Hare Intl

7h 19m

1 stop

BOS2:29 pmBoston Logan Intl

$212

JetBlue

Oct 21

BOS5:12 pmBoston Logan Intl

3h 02m

ORD7:14 pmChicago O'Hare Intl

Oct 26

ORD1:00 pmChicago O'Hare Intl

2h 48m

BOS4:48 pmBoston Logan Intl

$213

JetBlue

Oct 15

BOS6:55 amBoston Logan Intl

2h 52m

ORD8:47 amChicago O'Hare Intl

Oct 19

ORD9:38 amChicago O'Hare Intl

2h 28m

BOS1:06 pmBoston Logan Intl

$217

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WorcesterChicago

ORH Worcester - ORD Chicago O'Hare Intl

ORHORD

Worcester

Wed 10/14

5:16 pm-10:30 pm

1 stop6h 14m

Chicago O'Hare Intl

Wed 10/21

8:29 am-4:49 pm

1 stop7h 20m

$204

WorcesterChicago

ORH Worcester - ORD Chicago O'Hare Intl

ORHORD

Worcester

Tue 10/13

4:15 pm-10:17 pm

1 stop7h 02m

Chicago O'Hare Intl

Tue 10/20

7:00 am-2:58 pm

1 stop6h 58m

$204

WorcesterChicago

ORH Worcester - ORD Chicago O'Hare Intl

ORHORD

Worcester

Tue 10/13

4:15 pm-8:43 pm

1 stop5h 28m

Chicago O'Hare Intl

Wed 10/21

8:36 am-2:58 pm

1 stop5h 22m

$204

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Thu 10/15

6:55 am-8:47 am

Nonstop2h 52m

Chicago O'Hare Intl

Tue 10/20

6:10 am-2:29 pm

1 stop7h 19m

$212

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Tue 10/13

6:55 am-8:47 am

Nonstop2h 52m

Chicago O'Hare Intl

Mon 10/19

6:10 am-2:29 pm

1 stop7h 19m

$212

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Wed 10/28

11:55 am-1:59 pm

Nonstop3h 04m

Chicago O'Hare Intl

Thu 10/29

6:59 am-12:26 pm

1 stop4h 27m

$212

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Thu 11/5

11:55 am-1:59 pm

Nonstop3h 04m

Chicago O'Hare Intl

Wed 11/11

7:00 am-12:26 pm

1 stop4h 26m

$212

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Thu 10/15

10:00 pm-11:40 pm

Nonstop2h 40m

Chicago Midway

Tue 10/20

8:10 am-2:55 pm

1 stop5h 45m

$212

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Tue 10/27

11:45 am-5:10 pm

1 stop6h 25m

Chicago Midway

Thu 10/29

6:45 pm-10:05 pm

Nonstop2h 20m

$212

Quickest round-trip

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sat 10/17

7:00 am-9:05 am

Nonstop3h 05m

Chicago O'Hare Intl

Thu 10/22

8:00 pm-11:36 pm

Nonstop2h 36m

$214

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 $197. 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 $217.

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 $326. 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 $424.

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 $293. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $369.

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 $267 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 $225 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.

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	$100
Fastest flight time	2h 10m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Massachusetts in the past 72 hours is $100. The best round-trip flight deal from Massachusetts to Chicago found on momondo in the last 72 hours is $204.

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

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 September 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 18.50% of the total bookings. Other popular models include Airbus A321neo with 11.54%, Boeing 737 MAX 8 with 11.45%, and Boeing 737 MAX 9 with 10.51%.

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 $72	Free Cancellation	Rating 7.1 3,040 reviews	Search JetBlue flights
Delta	PriceFrom $88	Free Cancellation	Rating 7.8 8,611 reviews	Search Delta flights
United Airlines	PriceFrom $134	Free Cancellation	Rating 7.4 10,251 reviews	Search United Airlines flights
Southwest	PriceFrom $145	Free Cancellation	Rating 8.0 4,201 reviews	Search Southwest flights
American Airlines	PriceFrom $147	Free Cancellation	Rating 7.0 12,099 reviews	Search American Airlines flights

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Saint Joseph

Lansing

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Schererville

Munster

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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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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 $100

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 10/21. 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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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

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?

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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