What is the cheapest airline that flies from Massachusetts to Chicago O'Hare Intl?

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

How long does it take to fly to Chicago O'Hare Intl Airport?

On average, it takes 2h 47m to fly from Massachusetts to Chicago O'Hare Intl Airport if you fly out of Boston (the most popular airport in Massachusetts) and into Chicago O'Hare Intl Airport (the most popular airport in Chicago O'Hare Intl Airport). If you’re flying out of Worcester and into Chicago O'Hare Intl Airport, then the flight time is around 4h 43m.

What airlines fly to Chicago O'Hare Intl Airport?

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

How many flights depart from Massachusetts to Chicago O'Hare Intl Airport on average per day?

As of November 2025, there are 72 flights per day flying from Massachusetts to Chicago O'Hare Intl Airport. The most common time of day flights depart is 4:00PM, with 47% of flights taking off in the afternoon.

How many operators does momondo search for flights from Massachusetts to Chicago O'Hare Intl Airport?

There are 7 operators available for flights from Massachusetts to Chicago O'Hare Intl Airport as of November 2025.

How old do you have to be to fly from Massachusetts to Chicago O'Hare Intl Airport?

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 O'Hare Intl Airport.

What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$59 Cheap Flights from Massachusetts to Chicago O'Hare Intl Airport in 2025/26

Q: How many flights depart from Massachusetts to Chicago O'Hare Intl Airport on average per week?

As of November 2025, 509 flights take off from Massachusetts and land in Chicago O'Hare Intl Airport each week. The most common flight departure day for this route is Tue, with 19% of weekly flights taking off on this day.

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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.

8:30 am - 10:35 amBOS-ORD

3h 05mnonstop

11:25 am - 2:49 pmORD-BOS

2h 24mnonstop

$117JetBlue

Find Deal

Wed, Dec 3 - Tue, Dec 9

8:30 am - 10:35 amBOS-ORD

3h 05mnonstop

8:38 pm - 12:06 amORD-BOS

2h 28mnonstop

$122JetBlue

Find Deal

Tue, Dec 9 - Fri, Dec 12

6:00 am - 8:17 amBOS-ORD

3h 17mnonstop

8:20 pm - 11:51 pmORD-BOS

2h 31mnonstop

$124American Airlines

Find Deal

Wed, Dec 17 - Thu, Dec 18

6:36 am - 8:47 amBOS-ORD

3h 11mnonstop

8:20 pm - 11:51 pmORD-BOS

2h 31mnonstop

$125American Airlines

Find Deal

Thu, Jan 1 - Mon, Jan 5

6:00 am - 8:00 amBOS-ORD

3h 00mnonstop

7:30 am - 10:49 amORD-BOS

2h 19mnonstop

$127United Airlines

Find Deal

Fri, Dec 5 - Sun, Dec 7

11:28 am - 5:27 pmBOS-ORD

6h 59m1 stop

6:00 am - 12:02 pmORD-BOS

5h 02m1 stop

$128Frontier

Find Deal

Thu, Dec 4 - Sun, Dec 7

6:00 am - 12:08 pmBOS-ORD

7h 08m1 stop

8:51 pm - 11:10 amORD-BOS

13h 19m1 stop

$130Frontier

Find Deal

Fri, Jan 16 - Sun, Jan 18

7:05 am - 9:17 amBDL-ORD

27h 12m2 stops

1:24 pm - 11:30 amORD-BDL

21h 06m1 stop

$239Multiple Airlines

Find Deal

Tue, Dec 2 - Sat, Dec 6

7:45 am - 8:42 pmBDL-ORD

13h 57m1 stop

8:45 am - 12:45 pmORD-BDL

27h 00m1 stop

$241Multiple Airlines

Find Deal

Fri, Dec 5 - Sun, Dec 7

6:10 am - 8:01 amBDL-ORD

2h 51mnonstop

6:13 pm - 9:31 pmORD-BDL

2h 18mnonstop

$247United Airlines

Find Deal

Sun, Dec 7 - Sun, Dec 14

American Airlines flights from Massachusetts to Chicago O'Hare Intl Airport

Our best American Airlines deals on Massachusetts to Chicago O'Hare Intl Airport flight tickets

American Airlines

Jan 1

BOS6:36 amBoston Logan Intl

3h 11m

ORD8:47 amChicago O'Hare Intl

Jan 5

ORD8:20 pmChicago O'Hare Intl

2h 31m

BOS11:51 pmBoston Logan Intl

$125

Find similar

American Airlines

Dec 14

BOS6:00 amBoston Logan Intl

3h 17m

ORD8:17 amChicago O'Hare Intl

Dec 18

ORD8:20 pmChicago O'Hare Intl

2h 31m

BOS11:51 pmBoston Logan Intl

$129

Find similar

American Airlines

Dec 12

BOS7:01 pmBoston Logan Intl

3h 13m

ORD9:14 pmChicago O'Hare Intl

Dec 14

ORD7:00 amChicago O'Hare Intl

2h 29m

BOS10:29 amBoston Logan Intl

$152

Find similar

United Airlines flights from Massachusetts to Chicago O'Hare Intl Airport

Our best United Airlines deals on Massachusetts to Chicago O'Hare Intl Airport flight tickets

United Airlines

Dec 9

BOS6:00 amBoston Logan Intl

3h 00m

ORD8:00 amChicago O'Hare Intl

Dec 12

ORD1:55 pmChicago O'Hare Intl

2h 20m

BOS5:15 pmBoston Logan Intl

$122

Find similar

United Airlines

Dec 5

BOS6:00 amBoston Logan Intl

3h 00m

ORD8:00 amChicago O'Hare Intl

Dec 7

ORD7:30 amChicago O'Hare Intl

2h 19m

BOS10:49 amBoston Logan Intl

$127

Find similar

United Airlines

Dec 13

BOS6:23 pmBoston Logan Intl

3h 00m

ORD8:23 pmChicago O'Hare Intl

Dec 20

ORD9:12 pmChicago O'Hare Intl

2h 33m

BOS12:45 amBoston Logan Intl

$132

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Massachusetts to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 12/3

8:30 am-10:35 am

Nonstop3h 05m

Chicago O'Hare Intl

Tue 12/9

11:25 am-2:49 pm

Nonstop2h 24m

$117

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 12/9

8:30 am-10:35 am

Nonstop3h 05m

Chicago O'Hare Intl

Fri 12/12

8:38 pm-12:06 am

Nonstop2h 28m

$122

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 12/17

6:00 am-8:17 am

Nonstop3h 17m

Chicago O'Hare Intl

Thu 12/18

8:20 pm-11:51 pm

Nonstop2h 31m

$124

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 1/1

6:36 am-8:47 am

Nonstop3h 11m

Chicago O'Hare Intl

Mon 1/5

8:20 pm-11:51 pm

Nonstop2h 31m

$125

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 12/5

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Sun 12/7

7:30 am-10:49 am

Nonstop2h 19m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 12/4

11:28 am-5:27 pm

1 stop6h 59m

Chicago O'Hare Intl

Sun 12/7

6:00 am-12:02 pm

1 stop5h 02m

$128

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 1/16

6:00 am-12:08 pm

1 stop7h 08m

Chicago O'Hare Intl

Sun 1/18

8:51 pm-11:10 am

1 stop13h 19m

$130

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Tue 12/2

7:05 am-9:17 am

2 stops27h 12m

Chicago O'Hare Intl

Sat 12/6

1:24 pm-11:30 am

1 stop21h 06m

$239

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Fri 12/5

7:45 am-8:42 pm

1 stop13h 57m

Chicago O'Hare Intl

Sun 12/7

8:45 am-12:45 pm

1 stop27h 00m

$241

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sun 12/7

6:10 am-8:01 am

Nonstop2h 51m

Chicago O'Hare Intl

Sun 12/14

6:13 pm-9:31 pm

Nonstop2h 18m

$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 O'Hare Intl Airport

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 O'Hare Intl Airport?

The month of January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Massachusetts averaging around $212.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $323. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Massachusetts because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $430.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Massachusetts in the evening is the least expensive time of day to depart. momondo users have found prices as low as $268 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $356. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Massachusetts to Chicago O'Hare Intl flight route?

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

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport from Massachusetts for as low as $222 on momondo.

What cabin class options are available on Massachusetts to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Massachusetts to Chicago O'Hare Intl 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 O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between Massachusetts to Chicago O'Hare Intl Airport.

Cheap Massachusetts to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Massachusetts to Chicago O'Hare Intl Airport

Best Price Found	$123
Fastest flight time	2h 26m
Direct flights	Every day

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

The fastest flight from Massachusetts to Chicago O'Hare Intl Airport takes 2h 26m

Direct flights go from Massachusetts to Chicago O'Hare Intl Airport every day.

Search flight deals

When did momondo last update prices for flights from Massachusetts to Chicago O'Hare Intl Airport?
Prices for flights from Massachusetts to Chicago O'Hare Intl Airport were last updated today.
How many operators does momondo search for flights from Massachusetts to Chicago O'Hare Intl Airport?
There are 7 operators available for flights from Massachusetts to Chicago O'Hare Intl Airport as of November 2025.
How old do you have to be to fly from Massachusetts to Chicago O'Hare Intl Airport?
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 O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Massachusetts to Chicago O'Hare Intl Airport?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Massachusetts to Chicago O'Hare Intl Airport is Boeing 737-800 (26.35% of total bookings). The next most popular plane models are Boeing 737-900 (12.55%), Boeing 737 MAX 8 (10.82%), and Airbus A220-300 (9.88%).

Best airlines flying from Massachusetts to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Massachusetts to Chicago O'Hare Intl Airport with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $71	Free Cancellation	Rating 6.3 8,146 reviews	Search Spirit Airlines flights
JetBlue	PriceFrom $79	Free Cancellation	Rating 7.2 2,905 reviews	Search JetBlue flights
Frontier	PriceFrom $89	Free Cancellation	Rating 5.8 3,103 reviews	Search Frontier flights
Delta	PriceFrom $116	Free Cancellation	Rating 7.9 8,008 reviews	Search Delta flights
United Airlines	PriceFrom $126	Free Cancellation	Rating 7.4 9,015 reviews	Search United Airlines flights
American Airlines	PriceFrom $135	Free Cancellation	Rating 7.2 11,047 reviews	Search American Airlines flights
Southwest	PriceFrom $156	Free Cancellation	Rating 8.0 4,245 reviews	Search Southwest flights

Lake Geneva

South Haven

Schaumburg

Rockford

Merrillville

Gurnee

Naperville

Rosemont

Kenosha

New Buffalo

Joliet

Oak Brook

Orland Park

Racine

Hammond

Tinley Park

Janesville

Aurora

Elgin

Benton Harbor

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Massachusetts to Chicago for you.

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

All flight searches from Massachusetts to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Massachusetts and alert you when they change.

An easier way to manage your Chicago O'Hare Intl Airport trip

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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 1/1. 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

Filter for what you want

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Find the cheapest flights from Massachusetts to Chicago

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American Airlines flights from Massachusetts to Chicago O'Hare Intl Airport

Our best American Airlines deals on Massachusetts to Chicago O'Hare Intl Airport flight tickets

United Airlines flights from Massachusetts to Chicago O'Hare Intl Airport

Our best United Airlines deals on Massachusetts to Chicago O'Hare Intl Airport flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Massachusetts to Chicago O'Hare Intl Airport that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Massachusetts to Chicago O'Hare Intl Airport

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 O'Hare Intl Airport?

The month of January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Massachusetts averaging around $212.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

What is the cheapest Massachusetts to Chicago O'Hare Intl flight route?

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

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

What cabin class options are available on Massachusetts to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Massachusetts to Chicago O'Hare Intl 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 O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between Massachusetts to Chicago O'Hare Intl Airport.

What is the cheapest airline that flies from Massachusetts to Chicago O'Hare Intl?

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

What airlines fly to Chicago O'Hare Intl Airport?

How many flights depart from Massachusetts to Chicago O'Hare Intl Airport on average per day?

As of November 2025, there are 72 flights per day flying from Massachusetts to Chicago O'Hare Intl Airport. The most common time of day flights depart is 4:00PM, with 47% of flights taking off in the afternoon.

How many flights depart from Massachusetts to Chicago O'Hare Intl Airport on average per week?

As of November 2025, 509 flights take off from Massachusetts and land in Chicago O'Hare Intl Airport each week. The most common flight departure day for this route is Tue, with 19% of weekly flights taking off on this day.

How long does it take to fly to Chicago O'Hare Intl Airport?

Cheap Massachusetts to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Massachusetts to Chicago O'Hare Intl Airport

Best Price Found

Fastest flight time

Direct flights

When did momondo last update prices for flights from Massachusetts to Chicago O'Hare Intl Airport?

How many operators does momondo search for flights from Massachusetts to Chicago O'Hare Intl Airport?

How old do you have to be to fly from Massachusetts to Chicago O'Hare Intl Airport?

What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

What is the most popular plane model from Massachusetts to Chicago O'Hare Intl Airport?

Best airlines flying from Massachusetts to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Massachusetts to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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 Chicago

Popular cities in the United States

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