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

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

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

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

What airlines fly to Massachusetts?

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Massachusetts from Chicago according to our data. United Airlines is the first choice among our users, with 36% of people opting to fly with this airline when traveling to Massachusetts. Keep in mind that there are 6 different airlines that fly to Massachusetts on a routine basis, so you have a few additional options to choose from.

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

As of February 2026, there are 74 flights per day flying from Chicago to Massachusetts. The most common time of day flights depart is 7:00AM, with 47% of flights taking off at noon.

When did momondo last update prices for flights from Chicago to Massachusetts?

Prices for flights from Chicago to Massachusetts were last updated today.

How many operators does momondo search for flights from Chicago to Massachusetts?

The number of operators available for flights from Chicago to Massachusetts is 6 as of February 2026.

How old do you have to be to fly from Chicago to Massachusetts?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Massachusetts.

What documentation or ID do you need to fly to Massachusetts?

The travel and health documents required for your trip to Massachusetts can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Massachusetts. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$69 Cheap Flights from Chicago to Massachusetts in 2026

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Find the cheapest flights from Chicago to Massachusetts

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:00 am - 9:27 am

ORD

BOS

2h 27mnonstop

7:40 pm - 9:50 pm

BOS

ORD

3h 10mnonstop

$130American Airlines

Sat, May 2 - Mon, May 4

6:23 pm - 9:59 pm

ORD

BOS

2h 36mnonstop

10:44 am - 12:31 pm

BOS

ORD

2h 47mnonstop

$131United Airlines

Sat, May 9 - Thu, Aug 20

3:55 pm - 7:30 pm

ORD

BOS

2h 35mnonstop

3:08 pm - 5:00 pm

BOS

ORD

2h 52mnonstop

$132United Airlines

Sat, May 30 - Wed, Jun 3

9:26 pm - 12:59 am

ORD

BOS

2h 33mnonstop

6:00 am - 7:58 am

BOS

ORD

2h 58mnonstop

$133United Airlines

Fri, Jun 5 - Sun, Jun 7

11:00 am - 2:24 pm

ORD

BOS

2h 24mnonstop

8:00 am - 10:10 am

BOS

ORD

3h 10mnonstop

$135JetBlue

Thu, Mar 12 - Tue, Mar 17

10:11 am - 1:35 pm

ORD

BOS

2h 24mnonstop

4:25 pm - 6:31 pm

BOS

ORD

3h 06mnonstop

$136Delta

Wed, Mar 4 - Wed, Mar 11

6:50 am - 10:11 am

ORD

BOS

2h 21mnonstop

7:35 pm - 9:29 pm

BOS

ORD

2h 54mnonstop

$137Delta

Thu, Apr 30 - Tue, May 5

7:55 am - 11:10 am

MDW

BOS

2h 15mnonstop

7:05 am - 9:00 am

BOS

MDW

2h 55mnonstop

$137Southwest

Fri, Mar 6 - Sun, Mar 8

4:35 pm - 11:55 pm

MDW

BOS

6h 20m

1 stop

7:05 am - 9:00 am

BOS

MDW

2h 55mnonstop

$142Southwest

Sat, Apr 4 - Sun, Apr 5

6:48 pm - 1:05 pm

ORD

ORH

17h 17m

1 stop

1:44 pm - 9:18 pm

ORH

ORD

8h 34m

1 stop

$162American Airlines

Wed, Mar 4 - Sun, Mar 8

JetBlue flights from Chicago to Massachusetts

Our best JetBlue deals on Chicago to Massachusetts flight tickets

JetBlue

Mar 12

ORD11:00 amChicago O'Hare Intl

2h 24m

BOS2:24 pmBoston Logan Intl

Mar 17

BOS8:00 amBoston Logan Intl

3h 10m

ORD10:10 amChicago O'Hare Intl

$135

JetBlue

Mar 12

ORD6:20 pmChicago O'Hare Intl

2h 33m

BOS9:53 pmBoston Logan Intl

Mar 16

BOS3:20 pmBoston Logan Intl

3h 04m

ORD5:24 pmChicago O'Hare Intl

$146

JetBlue

Feb 26

ORD10:00 amChicago O'Hare Intl

2h 20m

BOS1:20 pmBoston Logan Intl

Mar 11

BOS7:00 amBoston Logan Intl

3h 10m

ORD9:10 amChicago O'Hare Intl

$152

Delta flights from Chicago to Massachusetts

Our best Delta deals on Chicago to Massachusetts flight tickets

Delta

Mar 4

ORD10:11 amChicago O'Hare Intl

2h 24m

BOS1:35 pmBoston Logan Intl

Mar 11

BOS4:25 pmBoston Logan Intl

3h 06m

ORD6:31 pmChicago O'Hare Intl

$136

Delta

Apr 30

ORD6:50 amChicago O'Hare Intl

2h 21m

BOS10:11 amBoston Logan Intl

May 5

BOS7:35 pmBoston Logan Intl

2h 54m

ORD9:29 pmChicago O'Hare Intl

$137

Delta

Mar 2

ORD7:05 amChicago O'Hare Intl

2h 32m

BOS10:37 amBoston Logan Intl

Mar 5

BOS7:15 amBoston Logan Intl

3h 13m

ORD9:28 amChicago O'Hare Intl

$145

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/2

6:00 am-9:27 am

Nonstop2h 27m

Boston Logan Intl

Mon 5/4

7:40 pm-9:50 pm

Nonstop3h 10m

$130

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/9

6:23 pm-9:59 pm

Nonstop2h 36m

Boston Logan Intl

Thu 8/20

10:44 am-12:31 pm

Nonstop2h 47m

$131

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/30

3:55 pm-7:30 pm

Nonstop2h 35m

Boston Logan Intl

Wed 6/3

3:08 pm-5:00 pm

Nonstop2h 52m

$132

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 6/5

9:26 pm-12:59 am

Nonstop2h 33m

Boston Logan Intl

Sun 6/7

6:00 am-7:58 am

Nonstop2h 58m

$133

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 3/12

11:00 am-2:24 pm

Nonstop2h 24m

Boston Logan Intl

Tue 3/17

8:00 am-10:10 am

Nonstop3h 10m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 3/4

10:11 am-1:35 pm

Nonstop2h 24m

Boston Logan Intl

Wed 3/11

4:25 pm-6:31 pm

Nonstop3h 06m

$136

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 4/30

6:50 am-10:11 am

Nonstop2h 21m

Boston Logan Intl

Tue 5/5

7:35 pm-9:29 pm

Nonstop2h 54m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 3/6

7:55 am-11:10 am

Nonstop2h 15m

Boston Logan Intl

Sun 3/8

7:05 am-9:00 am

Nonstop2h 55m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 4/4

4:35 pm-11:55 pm

1 stop6h 20m

Boston Logan Intl

Sun 4/5

7:05 am-9:00 am

Nonstop2h 55m

$142

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Wed 3/4

6:48 pm-1:05 pm

1 stop17h 17m

Worcester

Sun 3/8

1:44 pm-9:18 pm

1 stop8h 34m

$162

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 Chicago to Massachusetts

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 Massachusetts?

In general, January is the cheapest month to fly from Chicago to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $190. If you aren’t able to travel to Massachusetts during the month of January, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $207.

What is the cheapest day to depart on your flight to Massachusetts?

According to our data, Wednesday is the cheapest day to fly to Massachusetts from Chicago. The lowest ticket price found for a Wednesday departure recently was $236. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $296.

What is the cheapest time of day to depart on your flight to Massachusetts?

Our data shows that the cheapest Chicago to Massachusetts flights are usually those with departure times in the evening. Our users have found flights to Massachusetts in the evening for as low as $211. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $291 on average. Flights to Massachusetts from Chicago at noon are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Chicago to Massachusetts flight route?

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

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

You are more likely to see cheaper flights to Massachusetts from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around $229 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from Chicago for as low as $189 on momondo.

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

There are 4 cabin classes available to choose from on Chicago to Massachusetts 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 Chicago to Massachusetts flights?

No. A direct flight is the cheapest option for a flight between Chicago to Massachusetts.

Cheap Chicago to Massachusetts flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Massachusetts

Best Price Found	$78
Fastest flight time	1h 50m
Direct flights	Every day
Airports in Massachusetts	140 airports

The best one-way flight to Massachusetts from Chicago in the past 72 hours is $78. The best round-trip flight deal from Chicago to Massachusetts found on momondo in the last 72 hours is $156.

The fastest flight from Chicago to Massachusetts takes 1h 50m

Direct flights go from Chicago to Massachusetts every day.

There are 140 airports in Massachusetts. From Chicago there are direct flights to Albany Intl (ALB), Hartford Bradley Intl (BDL).

Search flight deals

When did momondo last update prices for flights from Chicago to Massachusetts?
Prices for flights from Chicago to Massachusetts were last updated today.
How many operators does momondo search for flights from Chicago to Massachusetts?
The number of operators available for flights from Chicago to Massachusetts is 6 as of February 2026.
How old do you have to be to fly from Chicago to Massachusetts?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Massachusetts.
What documentation or ID do you need to fly to Massachusetts?
The travel and health documents required for your trip to Massachusetts can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Massachusetts. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to Massachusetts?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to Massachusetts is Boeing 737-800 (19.98% of total bookings). The next most popular plane models are Embraer 175 (17.61%), Boeing 737 MAX 9 (9.04%), and Airbus A220-300 (8.83%).

Best airlines flying from Chicago to Massachusetts

Compare and see reviews for airlines that fly from Chicago to Massachusetts with momondo

Airline	Rating	Free Cancellation	Price
JetBlue	PriceFrom $62	Free Cancellation	Rating 7.2 2,900 reviews	Search JetBlue flights
Spirit Airlines	PriceFrom $79	Free Cancellation	Rating 6.3 8,470 reviews	Search Spirit Airlines flights
Delta	PriceFrom $91	Free Cancellation	Rating 7.9 8,207 reviews	Search Delta flights
American Airlines	PriceFrom $117	Free Cancellation	Rating 7.2 11,304 reviews	Search American Airlines flights
United Airlines	PriceFrom $117	Free Cancellation	Rating 7.4 9,314 reviews	Search United Airlines flights
Southwest	PriceFrom $127	Free Cancellation	Rating 8.0 4,294 reviews	Search Southwest flights

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Massachusetts from Chicago.

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

Yes. momondo enables you to select and highlight flights to Massachusetts from Chicago with this policy.

How can momondo help me find flights from Chicago to Massachusetts?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Massachusetts.

I’m not ready to book a flight from Chicago to Massachusetts right now. Can momondo alert me if prices change?

Price alerts on flights to Massachusetts from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Massachusetts trip

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Cheap flights from Chicago to Massachusetts from $69

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Massachusetts departing on 4/21. 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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Our best JetBlue deals on Chicago to Massachusetts flight tickets

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See travel insights to Massachusetts from

How to get the cheapest flight ticket from Chicago to Massachusetts

What is the cheapest month to fly to Massachusetts?

What is the cheapest day to depart on your flight to Massachusetts?

What is the cheapest time of day to depart on your flight to Massachusetts?

What is the cheapest Chicago to Massachusetts flight route?

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

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

Can stopping save me money on Chicago to Massachusetts flights?

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

What airlines fly to Massachusetts?

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

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

Cheap Chicago to Massachusetts flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Massachusetts

Best Price Found

Fastest flight time

Direct flights

Airports in Massachusetts

Best airlines flying from Chicago to Massachusetts

Compare and see reviews for airlines that fly from Chicago to Massachusetts with momondo

Why use momondo?

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

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

How can momondo help me find flights from Chicago to Massachusetts?

I’m not ready to book a flight from Chicago to Massachusetts right now. Can momondo alert me if prices change?

An easier way to manage your Massachusetts 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 Massachusetts

Popular cities in Massachusetts

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According to popular flight searches on momondo this year

Massachusetts flight routes

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