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 5 different airlines that fly to Chicago O'Hare Intl Airport 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 O'Hare Intl?

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

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

As of June 2026, there are 103 flights per day flying from Massachusetts to Chicago O'Hare Intl Airport. The most common time of day flights depart is 3:00PM, with 49% of flights taking off in the afternoon.

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

On average, it takes 2h 50m 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 West Tisbury and into Chicago O'Hare Intl Airport, then the flight time is around 4h 28m.

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

There are 5 operators available for flights from Massachusetts to Chicago O'Hare Intl Airport as of June 2026.

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.

$79 Cheap Flights from Massachusetts to Chicago O'Hare Intl Airport in 2026

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

As of June 2026, 723 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 Fri, with 16% of weekly flights taking off on this day.

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.

5:26 pm - 9:58 pm

MVY

ORD

5h 32m

1 stop

9:40 am - 4:10 pm

ORD

MVY

5h 30m

1 stop

$158JetBlue

Tue, Jul 14 - Wed, Jul 15

5:05 pm - 9:55 pm

MVY

ORD

5h 50m

1 stop

9:39 am - 4:09 pm

ORD

MVY

5h 30m

1 stop

$166JetBlue

Thu, Aug 20 - Tue, Aug 25

7:19 am - 9:17 am

BOS

ORD

2h 58mnonstop

6:05 am - 9:29 am

ORD

BOS

2h 24mnonstop

$182United Airlines

Wed, Jul 1 - Sun, Jul 5

1:30 pm - 3:23 pm

BOS

ORD

2h 53mnonstop

4:30 pm - 8:11 pm

ORD

BOS

2h 41mnonstop

$183Delta

Sat, Jul 11 - Sat, Jul 25

5:45 am - 9:36 am

BOS

ORD

4h 51m

1 stop

6:05 am - 9:29 am

ORD

BOS

2h 24mnonstop

$189United Airlines

Fri, Jul 10 - Tue, Jul 14

7:30 am - 9:26 am

BOS

ORD

2h 56mnonstop

7:25 pm - 11:00 pm

ORD

BOS

2h 35mnonstop

$191Delta

Sat, Jul 11 - Mon, Jul 13

5:16 pm - 11:30 pm

ORH

ORD

7h 14m

1 stop

5:00 am - 4:51 pm

ORD

ORH

10h 51m

1 stop

$192American Airlines

Sat, Jul 11 - Sat, Jul 18

5:16 pm - 2:15 pm

ORH

ORD

21h 59m

1 stop

6:37 am - 4:51 pm

ORD

ORH

9h 14m

1 stop

$200American Airlines

Mon, Jul 13 - Fri, Jul 17

8:02 pm - 12:15 pm

ALB

ORD

17h 13m

1 stop

5:29 pm - 10:25 am

ORD

ALB

39h 56m

2 stops

$335Multiple Airlines

Mon, Aug 10 - Fri, Aug 28

4:36 pm - 12:15 pm

ALB

ORD

20h 39m

2 stops

8:05 am - 7:12 pm

ORD

ALB

10h 07m

1 stop

$341Multiple Airlines

Thu, Aug 13 - Mon, Aug 17

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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

American Airlines

Jun 25

BOS10:29 amBoston Logan Intl

3h 01m

ORD12:30 pmChicago O'Hare Intl

Jul 3

ORD4:03 pmChicago O'Hare Intl

2h 51m

BOS7:54 pmBoston Logan Intl

$187

American Airlines

Oct 21

BOS5:24 amBoston Logan Intl

3h 01m

ORD7:25 amChicago O'Hare Intl

Oct 25

ORD6:45 amChicago O'Hare Intl

2h 21m

BOS10:06 amBoston Logan Intl

$190

American Airlines

Jul 11

ORH5:16 pmWorcester

7h 14m

1 stop

ORD11:30 pmChicago O'Hare Intl

Jul 18

ORD5:00 amChicago O'Hare Intl

10h 51m

1 stop

ORH4:51 pmWorcester

$192

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

Jul 1

BOS7:19 amBoston Logan Intl

2h 58m

ORD9:17 amChicago O'Hare Intl

Jul 5

ORD6:05 amChicago O'Hare Intl

2h 24m

BOS9:29 amBoston Logan Intl

$182

United Airlines

Sep 23

BOS8:31 pmBoston Logan Intl

2h 59m

ORD10:30 pmChicago O'Hare Intl

Sep 27

ORD6:00 amChicago O'Hare Intl

4h 24m

1 stop

BOS11:24 amBoston Logan Intl

$184

United Airlines

Sep 17

BOS9:00 amBoston Logan Intl

2h 59m

ORD10:59 amChicago O'Hare Intl

Sep 20

ORD6:10 amChicago O'Hare Intl

2h 23m

BOS9:33 amBoston Logan Intl

$188

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

Cheapest round-trip

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Tue 7/14

5:26 pm-9:58 pm

1 stop5h 32m

Chicago O'Hare Intl

Wed 7/15

9:40 am-4:10 pm

1 stop5h 30m

$158

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Thu 8/20

5:05 pm-9:55 pm

1 stop5h 50m

Chicago O'Hare Intl

Tue 8/25

9:39 am-4:09 pm

1 stop5h 30m

$166

Quickest round-trip

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 7/1

7:19 am-9:17 am

Nonstop2h 58m

Chicago O'Hare Intl

Sun 7/5

6:05 am-9:29 am

Nonstop2h 24m

$182

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 7/11

1:30 pm-3:23 pm

Nonstop2h 53m

Chicago O'Hare Intl

Sat 7/25

4:30 pm-8:11 pm

Nonstop2h 41m

$183

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 7/10

5:45 am-9:36 am

1 stop4h 51m

Chicago O'Hare Intl

Tue 7/14

6:05 am-9:29 am

Nonstop2h 24m

$189

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 7/11

7:30 am-9:26 am

Nonstop2h 56m

Chicago O'Hare Intl

Mon 7/13

7:25 pm-11:00 pm

Nonstop2h 35m

$191

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Sat 7/11

5:16 pm-11:30 pm

1 stop7h 14m

Chicago O'Hare Intl

Sat 7/18

5:00 am-4:51 pm

1 stop10h 51m

$192

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Mon 7/13

5:16 pm-2:15 pm

1 stop21h 59m

Chicago O'Hare Intl

Fri 7/17

6:37 am-4:51 pm

1 stop9h 14m

$200

AlbanyChicago

ALB - ORD

ALBORD

Albany Intl

Mon 8/10

8:02 pm-12:15 pm

1 stop17h 13m

Chicago O'Hare Intl

Fri 8/28

5:29 pm-10:25 am

2 stops39h 56m

$335

AlbanyChicago

ALB - ORD

ALBORD

Albany Intl

Thu 8/13

4:36 pm-12:15 pm

2 stops20h 39m

Chicago O'Hare Intl

Mon 8/17

8:05 am-7:12 pm

1 stop10h 07m

$341

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 February is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Massachusetts averaging around $68.

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 $315. 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 $405.

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 $269 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $389. 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 from Massachusetts 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 $252 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 $202 on momondo.

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

There are 4 cabin classes available to choose from on Massachusetts to Chicago O'Hare Intl Airport 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	$138
Fastest flight time	2h 23m
Direct flights	Every day

The best one-way flight to Chicago O'Hare Intl Airport from Massachusetts in the past 72 hours is $138. The best round-trip flight deal from Massachusetts to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $247.

The fastest flight from Massachusetts to Chicago O'Hare Intl Airport takes 2h 23m

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

Search flight deals

Frequently asked questions about flying from Massachusetts to Chicago O'Hare Intl Airport

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 5 operators available for flights from Massachusetts to Chicago O'Hare Intl Airport as of June 2026.
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 (19.71% of total bookings). The next most popular plane models are Airbus A321neo (11.95%), Airbus A319 (11.18%), and Boeing 737-900 (10.89%).

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
JetBlue	PriceFrom $68	Free Cancellation	Rating 7.1 2,981 reviews	Search JetBlue flights
Delta	PriceFrom $88	Free Cancellation	Rating 7.9 8,403 reviews	Search Delta flights
United Airlines	PriceFrom $124	Free Cancellation	Rating 7.4 9,820 reviews	Search United Airlines flights
American Airlines	PriceFrom $137	Free Cancellation	Rating 7.1 11,657 reviews	Search American Airlines flights
Southwest	PriceFrom $156	Free Cancellation	Rating 7.9 4,234 reviews	Search Southwest flights

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Schaumburg

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Rockford

Merrillville

Gurnee

Rosemont

Naperville

Orland Park

Oak Brook

New Buffalo

Joliet

Kenosha

Aurora

Hammond

Racine

Janesville

Evanston

Elgin

South Holland

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.

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Cheap flights from Massachusetts to Chicago from $79

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 7/8. 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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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

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

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

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

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?

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

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

Can stopping save me money on Massachusetts to Chicago O'Hare Intl Airport flights?

What is the cheapest airline that flies 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?

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

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

Frequently asked questions about flying 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?

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

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

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