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Cheap flights from Chicago O'Hare Intl Airport to Massachusetts from $64

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 O'Hare Intl Airport to Massachusetts departing on 2/18. 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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Find the cheapest flights from Chicago O'Hare Intl Airport to Massachusetts

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
5:25 pm - 8:45 pm
ORD
-
BOS
2h 20mnonstop
American Airlines Logo
7:00 am - 9:05 am
BOS
-
ORD
3h 05mnonstop
$127American Airlines
Sat, Jan 17 - Sun, Jan 18
Frontier Logo
6:02 pm - 1:13 am
ORD
-
BOS
6h 11m1 stop
Frontier Logo
6:00 am - 4:52 pm
BOS
-
ORD
11h 52m1 stop
$128Frontier
Tue, Feb 24 - Wed, Feb 25
JetBlue Logo
10:00 am - 1:20 pm
ORD
-
BOS
2h 20mnonstop
JetBlue Logo
7:00 am - 9:10 am
BOS
-
ORD
3h 10mnonstop
$130JetBlue
Sat, Feb 14 - Tue, Feb 17
Multiple Airlines Logo
7:20 am - 4:28 pm
ORD
-
BOS
8h 08m1 stop
Multiple Airlines Logo
6:00 am - 1:58 pm
BOS
-
ORD
8h 58m1 stop
$131Multiple Airlines
Sat, Jan 24 - Tue, Jan 27
Multiple Airlines Logo
7:45 am - 11:10 am
ORD
-
BOS
2h 25mnonstop
Multiple Airlines Logo
7:00 am - 5:52 pm
BOS
-
ORD
11h 52m1 stop
$132Multiple Airlines
Fri, Feb 6 - Sat, Feb 7
JetBlue Logo
7:45 am - 11:10 am
ORD
-
BOS
2h 25mnonstop
JetBlue Logo
3:35 pm - 5:43 pm
BOS
-
ORD
3h 08mnonstop
$135JetBlue
Thu, Jan 22 - Mon, Jan 26
Delta Logo
7:05 am - 10:37 am
ORD
-
BOS
2h 32mnonstop
Delta Logo
11:35 am - 1:41 pm
BOS
-
ORD
3h 06mnonstop
$137Delta
Sat, Feb 28 - Wed, Mar 4
Delta Logo
12:30 pm - 8:08 pm
ORD
-
BDL
6h 38m1 stop
Delta Logo
5:40 am - 9:41 am
BDL
-
ORD
5h 01m1 stop
$177Delta
Sat, Jan 17 - Sun, Jan 18
United Airlines Logo
6:06 pm - 9:22 pm
ORD
-
ALB
2h 16mnonstop
United Airlines Logo
6:00 am - 7:46 am
ALB
-
ORD
2h 46mnonstop
$223United Airlines
Sat, Jan 17 - Sun, Jan 18
United Airlines Logo
10:55 am - 2:10 pm
ORD
-
BDL
2h 15mnonstop
United Airlines Logo
10:05 am - 11:57 am
BDL
-
ORD
2h 52mnonstop
$225United Airlines
Sat, Feb 14 - Tue, Feb 17

Delta flights from Chicago O'Hare Intl Airport to Massachusetts

Our best Delta deals on Chicago O'Hare Intl Airport to Massachusetts flight tickets
Delta
Feb 28
ORD7:05 amChicago O'Hare Intl
2h 32m
BOS10:37 amBoston Logan Intl
Mar 11
BOS4:25 pmBoston Logan Intl
3h 06m
ORD6:31 pmChicago O'Hare Intl
$137
Find similar
Delta
Jan 17
ORD12:30 pmChicago O'Hare Intl
6h 38m
1 stop
BDL8:08 pmHartford Bradley Intl
Jan 18
BDL5:40 amHartford Bradley Intl
5h 01m
1 stop
ORD9:41 amChicago O'Hare Intl
$177
Find similar
Delta
Jan 1
ORD7:05 amChicago O'Hare Intl
2h 31m
BOS10:36 amBoston Logan Intl
Jan 6
BOS7:55 pmBoston Logan Intl
3h 06m
ORD10:01 pmChicago O'Hare Intl
$197
Find similar

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

Our best United Airlines deals on Chicago O'Hare Intl Airport to Massachusetts flight tickets
United Airlines
Dec 31
ORD6:11 pmChicago O'Hare Intl
2h 33m
BOS9:44 pmBoston Logan Intl
Jan 1
BOS6:29 pmBoston Logan Intl
3h 06m
ORD8:35 pmChicago O'Hare Intl
$127
Find similar
United Airlines
Dec 31
ORD6:11 pmChicago O'Hare Intl
2h 33m
BOS9:44 pmBoston Logan Intl
Jan 1
BOS7:45 amBoston Logan Intl
3h 04m
ORD9:49 amChicago O'Hare Intl
$132
Find similar
United Airlines
Jan 6
ORD9:13 amChicago O'Hare Intl
2h 33m
BOS12:46 pmBoston Logan Intl
Jan 6
BOS4:49 pmBoston Logan Intl
3h 00m
ORD6:49 pmChicago O'Hare Intl
$147
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated December 26, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Massachusetts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/17

5:25 pm-8:45 pm

Nonstop2h 20m

Boston Logan Intl

Sun 1/18

7:00 am-9:05 am

Nonstop3h 05m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 2/24

6:02 pm-1:13 am

1 stop6h 11m

Boston Logan Intl

Wed 2/25

6:00 am-4:52 pm

1 stop11h 52m

$128

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 2/14

10:00 am-1:20 pm

Nonstop2h 20m

Boston Logan Intl

Tue 2/17

7:00 am-9:10 am

Nonstop3h 10m

$130

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/24

7:20 am-4:28 pm

1 stop8h 08m

Boston Logan Intl

Tue 1/27

6:00 am-1:58 pm

1 stop8h 58m

$131

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 2/6

7:45 am-11:10 am

Nonstop2h 25m

Boston Logan Intl

Sat 2/7

7:00 am-5:52 pm

1 stop11h 52m

$132

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/22

7:45 am-11:10 am

Nonstop2h 25m

Boston Logan Intl

Mon 1/26

3:35 pm-5:43 pm

Nonstop3h 08m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 2/28

7:05 am-10:37 am

Nonstop2h 32m

Boston Logan Intl

Wed 3/4

11:35 am-1:41 pm

Nonstop3h 06m

$137

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Sat 1/17

12:30 pm-8:08 pm

1 stop6h 38m

Hartford Bradley Intl

Sun 1/18

5:40 am-9:41 am

1 stop5h 01m

$177

ChicagoAlbany

ORD - ALB

ORDALB

Chicago O'Hare Intl

Sat 1/17

6:06 pm-9:22 pm

Nonstop2h 16m

Albany Intl

Sun 1/18

6:00 am-7:46 am

Nonstop2h 46m

$223

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Sat 2/14

10:55 am-2:10 pm

Nonstop2h 15m

Hartford Bradley Intl

Tue 2/17

10:05 am-11:57 am

Nonstop2h 52m

$225

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Massachusetts from

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

What is the cheapest month to fly to Massachusetts?

In general, September is the cheapest month to fly from Chicago O'Hare Intl Airport to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $192. If you aren’t able to travel to Massachusetts during the month of September, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $194.

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

According to our data, Thursday is the cheapest day to fly to Massachusetts from Chicago O'Hare Intl Airport. The lowest ticket price found for a Thursday departure recently was $241. 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 O'Hare Intl Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $306.

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

Our data shows that the cheapest Chicago O'Hare Intl Airport 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 $214. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $298 on average. Flights to Massachusetts from Chicago O'Hare Intl Airport at noon are generally more expensive because this time of day is more convenient for travelers’ schedules.

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

Fly from Chicago O'Hare Intl to Boston Logan Intl for the best Chicago O'Hare Intl - 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 O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around $231 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from Chicago O'Hare Intl Airport for as low as $183 on momondo.

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

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

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

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

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

Best Price Found

$90

Fastest flight time

1h 57m

Direct flights

Every day

Airports in Massachusetts

140 airports
The best one-way flight to Massachusetts from Chicago O'Hare Intl Airport in the past 72 hours is $90. The best round-trip flight deal from Chicago O'Hare Intl Airport to Massachusetts found on momondo in the last 72 hours is $188.
The fastest flight from Chicago O'Hare Intl Airport to Massachusetts takes 1h 57m
Direct flights go from Chicago O'Hare Intl Airport to Massachusetts every day.
There are 140 airports in Massachusetts. From Chicago O'Hare Intl Airport there are direct flights to Albany Intl (ALB), Boston Logan Intl (BOS), Hartford Bradley Intl (BDL).
Search flight deals

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

    Prices for flights from Chicago O'Hare Intl Airport to Massachusetts are updated daily.

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago O'Hare Intl Airport to Massachusetts.

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

    The travel and health documents you'll need for your trip to Massachusetts may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Massachusetts. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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

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

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Massachusetts with momondo
Airline
Rating
Free Cancellation
Price
JetBluePriceFrom $78Free CancellationRating
7.2
2,900 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $83Free CancellationRating
6.3
8,208 reviews
Search Spirit Airlines flights
DeltaPriceFrom $103Free CancellationRating
7.9
8,014 reviews
Search Delta flights
FrontierPriceFrom $104Free CancellationRating
5.8
3,070 reviews
Search Frontier flights
American AirlinesPriceFrom $117Free CancellationRating
7.2
11,064 reviews
Search American Airlines flights
United AirlinesPriceFrom $117Free CancellationRating
7.4
9,116 reviews
Search United Airlines flights
SouthwestPriceFrom $144Free CancellationRating
8.0
4,258 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?

momondo does allow users to show only those flights to Massachusetts from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

momondo provides multiple filters to help you find the best flight to Massachusetts from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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.

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