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 West Tisbury to Chicago O'Hare Intl Airport is 5h 03m 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?

84 flights are operational daily from Massachusetts to Chicago as of November 2025. The most popular departure time for this route is 4:00PM, with 47% of flights per day taking off in the afternoon.

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

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

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

591 flights are operational weekly from Massachusetts to Chicago as of November 2025. The most popular departure day for this route is Sun, with 21% of flights per week taking off on this day.

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 39% 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.

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 November 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.

$59 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

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Cheap round-trip flights

Enter your travel dates to find the best prices.

5:20 am - 7:05 amBOS-MDW

2h 45mnonstop

6:15 pm - 9:35 pmMDW-BOS

2h 20mnonstop

$117Southwest

Find Deal

Sat, Dec 13 - Wed, Dec 17

8:30 am - 10:35 amBOS-ORD

3h 05mnonstop

8:38 pm - 12:06 amORD-BOS

2h 28mnonstop

$117JetBlue

Find Deal

Wed, Dec 3 - Thu, Dec 4

6:00 am - 8:17 amBOS-ORD

3h 17mnonstop

7:00 am - 10:29 amORD-BOS

2h 29mnonstop

$123American Airlines

Find Deal

Sat, Dec 13 - Sun, Dec 14

6:00 am - 11:31 amBOS-MDW

6h 31m1 stop

12:41 pm - 1:19 amMDW-BOS

11h 38m1 stop

$124Frontier

Find Deal

Thu, Jan 8 - Sun, Jan 11

11:28 am - 10:24 pmBOS-ORD

11h 56m1 stop

6:00 am - 12:02 pmORD-BOS

5h 02m1 stop

$124Frontier

Find Deal

Thu, Dec 11 - Sun, Dec 14

6:23 pm - 8:23 pmBOS-ORD

3h 00mnonstop

7:30 am - 10:49 amORD-BOS

2h 19mnonstop

$127United Airlines

Find Deal

Fri, Dec 5 - Sun, Dec 7

8:11 pm - 9:48 amBOS-RFD

14h 37m1 stop

10:38 am - 9:52 amRFD-BOS

22h 14m1 stop

$217Multiple Airlines

Find Deal

Sun, Dec 14 - Wed, Dec 17

4:26 pm - 10:48 pmORH-ORD

7h 22m1 stop

8:47 pm - 2:53 pmORD-ORH

17h 06m1 stop

$224American Airlines

Find Deal

Wed, Apr 15 - Sat, Apr 25

12:57 pm - 9:48 amBOS-RFD

21h 51m1 stop

10:38 am - 9:52 amRFD-BOS

22h 14m1 stop

$227Multiple Airlines

Find Deal

Sun, Dec 14 - Wed, Dec 17

6:10 am - 8:01 amBDL-ORD

2h 51mnonstop

1:05 pm - 6:53 pmORD-BDL

4h 48m1 stop

$245United Airlines

Find Deal

Thu, Dec 11 - Sat, Dec 13

JetBlue flights from Massachusetts to Chicago

Our best JetBlue deals on Massachusetts to Chicago flight tickets

JetBlue

Dec 3

BOS8:30 amBoston Logan Intl

3h 05m

ORD10:35 amChicago O'Hare Intl

Dec 6

ORD11:25 amChicago O'Hare Intl

2h 24m

BOS2:49 pmBoston Logan Intl

$117

Find similar

JetBlue

Apr 25

BOS3:39 pmBoston Logan Intl

2h 52m

ORD5:31 pmChicago O'Hare Intl

Apr 28

ORD11:30 amChicago O'Hare Intl

2h 26m

BOS2:56 pmBoston Logan Intl

$119

Find similar

JetBlue

Jan 21

BOS3:35 pmBoston Logan Intl

3h 09m

ORD5:44 pmChicago O'Hare Intl

Jan 26

ORD7:45 amChicago O'Hare Intl

2h 25m

BOS11:10 amBoston Logan Intl

$121

Find similar

American Airlines flights from Massachusetts to Chicago

Our best American Airlines deals on Massachusetts to Chicago flight tickets

American Airlines

Dec 13

BOS6:00 amBoston Logan Intl

3h 17m

ORD8:17 amChicago O'Hare Intl

Dec 14

ORD7:00 amChicago O'Hare Intl

2h 29m

BOS10:29 amBoston Logan Intl

$123

Find similar

American Airlines

Dec 13

BOS6:00 amBoston Logan Intl

3h 17m

ORD8:17 amChicago O'Hare Intl

Dec 20

ORD8:53 pmChicago O'Hare Intl

2h 27m

BOS12:20 amBoston Logan Intl

$129

Find similar

American Airlines

Nov 22

BOS6:45 amBoston Logan Intl

3h 07m

ORD8:52 amChicago O'Hare Intl

Nov 24

ORD8:08 pmChicago O'Hare Intl

2h 33m

BOS11:41 pmBoston Logan Intl

$149

Find similar

Fly from

Fly to

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 12/13

5:20 am-7:05 am

Nonstop2h 45m

Chicago Midway

Wed 12/17

6:15 pm-9:35 pm

Nonstop2h 20m

$117

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 12/3

8:30 am-10:35 am

Nonstop3h 05m

Chicago O'Hare Intl

Thu 12/4

8:38 pm-12:06 am

Nonstop2h 28m

$117

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 12/13

6:00 am-8:17 am

Nonstop3h 17m

Chicago O'Hare Intl

Sun 12/14

7:00 am-10:29 am

Nonstop2h 29m

$123

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 1/8

6:00 am-11:31 am

1 stop6h 31m

Chicago Midway

Sun 1/11

12:41 pm-1:19 am

1 stop11h 38m

$124

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 12/11

11:28 am-10:24 pm

1 stop11h 56m

Chicago O'Hare Intl

Sun 12/14

6:00 am-12:02 pm

1 stop5h 02m

$124

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 12/5

6:23 pm-8:23 pm

Nonstop3h 00m

Chicago O'Hare Intl

Sun 12/7

7:30 am-10:49 am

Nonstop2h 19m

$127

BostonChicago

BOS - RFD

BOSRFD

Boston Logan Intl

Sun 12/14

8:11 pm-9:48 am

1 stop14h 37m

Chicago Greater Rockford

Wed 12/17

10:38 am-9:52 am

1 stop22h 14m

$217

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 4/15

4:26 pm-10:48 pm

1 stop7h 22m

Chicago O'Hare Intl

Sat 4/25

8:47 pm-2:53 pm

1 stop17h 06m

$224

BostonChicago

BOS - RFD

BOSRFD

Boston Logan Intl

Sun 12/14

12:57 pm-9:48 am

1 stop21h 51m

Chicago Greater Rockford

Wed 12/17

10:38 am-9:52 am

1 stop22h 14m

$227

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 12/11

6:10 am-8:01 am

Nonstop2h 51m

Chicago O'Hare Intl

Sat 12/13

1:05 pm-6:53 pm

1 stop4h 48m

$245

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 September is, on average, the cheapest month to fly to Chicago from Massachusetts, with most prices found around $187. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Massachusetts to Chicago during January average around $192.

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 Wednesday 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 $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 $272. 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 Midway 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 $222 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	$123
Fastest flight time	2h 10m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Massachusetts in the past 72 hours is $123. The best round-trip flight deal from Massachusetts to Chicago found on momondo in the last 72 hours is $191.

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

Direct flights go from Massachusetts to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), 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 November 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 25.65% of the total bookings. Other popular models include Boeing 737-900 with 12.29%, Boeing 737 MAX 8 with 11.16%, and Airbus A220-300 with 9.71%.

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 $71	Free Cancellation	Rating 6.3 8,142 reviews	Search Spirit Airlines flights
JetBlue	PriceFrom $79	Free Cancellation	Rating 7.2 2,904 reviews	Search JetBlue flights
Frontier	PriceFrom $89	Free Cancellation	Rating 5.8 3,109 reviews	Search Frontier flights
Delta	PriceFrom $116	Free Cancellation	Rating 7.9 8,010 reviews	Search Delta flights
Southwest	PriceFrom $117	Free Cancellation	Rating 8.0 4,245 reviews	Search Southwest flights
United Airlines	PriceFrom $126	Free Cancellation	Rating 7.4 9,016 reviews	Search United Airlines flights
American Airlines	PriceFrom $135	Free Cancellation	Rating 7.2 11,051 reviews	Search American Airlines flights

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Saint Joseph

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Schererville

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 $59

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 1/6. 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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Filter for what you want

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JetBlue flights from Massachusetts to Chicago

Our best JetBlue deals on Massachusetts to Chicago flight tickets

American Airlines flights from Massachusetts to Chicago

Our best American Airlines 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.

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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

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 $272. 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 Midway 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?

JetBlue, Frontier, and Southwest 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?

84 flights are operational daily from Massachusetts to Chicago as of November 2025. The most popular departure time for this route is 4:00PM, with 47% of flights per day taking off in the afternoon.

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

591 flights are operational weekly from Massachusetts to Chicago as of November 2025. The most popular departure day for this route is Sun, with 21% 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