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Cheap flights from Chicago O'Hare Intl Airport to Massachusetts from $68

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 2/16. 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.
United Airlines Logo
9:30 pm - 12:59 am
ORD
-
BOS
2h 29mnonstop
United Airlines Logo
6:00 am - 8:00 am
BOS
-
ORD
3h 00mnonstop
$131United Airlines
Fri, May 8 - Sun, May 10
JetBlue Logo
12:41 pm - 7:58 pm
ORD
-
BOS
6h 17m
1 stop
JetBlue Logo
7:00 am - 9:10 am
BOS
-
ORD
3h 10mnonstop
$133JetBlue
Thu, Mar 5 - Sun, Mar 8
Multiple Airlines Logo
11:00 am - 2:24 pm
ORD
-
BOS
2h 24mnonstop
Multiple Airlines Logo
5:45 am - 5:15 pm
BOS
-
ORD
12h 30m
1 stop
$134Multiple Airlines
Thu, Mar 12 - Wed, Mar 18
American Airlines Logo
6:05 am - 9:32 am
ORD
-
BOS
2h 27mnonstop
American Airlines Logo
5:29 am - 7:25 am
BOS
-
ORD
2h 56mnonstop
$135American Airlines
Wed, Aug 5 - Tue, Aug 11
JetBlue Logo
10:00 am - 1:20 pm
ORD
-
BOS
2h 20mnonstop
JetBlue Logo
7:00 am - 9:10 am
BOS
-
ORD
3h 10mnonstop
$136JetBlue
Tue, Feb 24 - Wed, Mar 11
American Airlines Logo
6:00 am - 9:27 am
ORD
-
BOS
2h 27mnonstop
American Airlines Logo
7:40 pm - 9:50 pm
BOS
-
ORD
3h 10mnonstop
$137American Airlines
Fri, Apr 10 - Sun, Apr 12
Multiple Airlines Logo
10:00 am - 1:20 pm
ORD
-
BOS
2h 20mnonstop
Multiple Airlines Logo
5:27 am - 7:11 pm
BOS
-
ORD
14h 44m
1 stop
$138Multiple Airlines
Wed, Feb 25 - Wed, Mar 11
Spirit Airlines Logo
5:15 am - 5:15 pm
ORD
-
BOS
11h 00m
1 stop
Spirit Airlines Logo
5:27 am - 7:11 pm
BOS
-
ORD
14h 44m
1 stop
$140Spirit Airlines
Wed, Mar 4 - Tue, Mar 10
Delta Logo
7:10 am - 3:33 pm
ORD
-
ORH
7h 23m
1 stop
Delta Logo
4:30 pm - 8:39 pm
ORH
-
ORD
5h 09m
1 stop
$192Delta
Thu, Feb 26 - Wed, Mar 4
Delta Logo
5:25 am - 3:33 pm
ORD
-
ORH
9h 08m
2 stops
Delta Logo
4:30 pm - 8:39 pm
ORH
-
ORD
5h 09m
1 stop
$202Delta
Thu, Feb 26 - Wed, Mar 4

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
May 8
ORD9:30 pmChicago O'Hare Intl
2h 29m
BOS12:59 amBoston Logan Intl
May 10
BOS6:00 amBoston Logan Intl
3h 00m
ORD8:00 amChicago O'Hare Intl
$131
United Airlines
Feb 17
ORD9:17 amChicago O'Hare Intl
2h 29m
BOS12:46 pmBoston Logan Intl
Feb 20
BOS7:45 amBoston Logan Intl
3h 05m
ORD9:50 amChicago O'Hare Intl
$145
United Airlines
Feb 13
ORD9:17 amChicago O'Hare Intl
2h 29m
BOS12:46 pmBoston Logan Intl
Feb 17
BOS9:40 amBoston Logan Intl
3h 06m
ORD11:46 amChicago O'Hare Intl
$149

JetBlue flights from Chicago O'Hare Intl Airport to Massachusetts

Our best JetBlue deals on Chicago O'Hare Intl Airport to Massachusetts flight tickets
JetBlue
Mar 5
ORD12:41 pmChicago O'Hare Intl
6h 17m
1 stop
BOS7:58 pmBoston Logan Intl
Mar 8
BOS7:00 amBoston Logan Intl
3h 10m
ORD9:10 amChicago O'Hare Intl
$133
JetBlue
Feb 15
ORD10:00 amChicago O'Hare Intl
2h 20m
BOS1:20 pmBoston Logan Intl
Feb 21
BOS7:00 amBoston Logan Intl
3h 10m
ORD9:10 amChicago O'Hare Intl
$134
JetBlue
Feb 15
ORD10:00 amChicago O'Hare Intl
2h 20m
BOS1:20 pmBoston Logan Intl
Feb 18
BOS7:00 amBoston Logan Intl
3h 10m
ORD9:10 amChicago O'Hare Intl
$135

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 February 11, 2026.
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

Fri 5/8

9:30 pm-12:59 am

Nonstop2h 29m

Boston Logan Intl

Sun 5/10

6:00 am-8:00 am

Nonstop3h 00m

$131

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 3/5

12:41 pm-7:58 pm

1 stop6h 17m

Boston Logan Intl

Sun 3/8

7:00 am-9:10 am

Nonstop3h 10m

$133

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 3/12

11:00 am-2:24 pm

Nonstop2h 24m

Boston Logan Intl

Wed 3/18

5:45 am-5:15 pm

1 stop12h 30m

$134

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 8/5

6:05 am-9:32 am

Nonstop2h 27m

Boston Logan Intl

Tue 8/11

5:29 am-7:25 am

Nonstop2h 56m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 2/24

10:00 am-1:20 pm

Nonstop2h 20m

Boston Logan Intl

Wed 3/11

7:00 am-9:10 am

Nonstop3h 10m

$136

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 4/10

6:00 am-9:27 am

Nonstop2h 27m

Boston Logan Intl

Sun 4/12

7:40 pm-9:50 pm

Nonstop3h 10m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 2/25

10:00 am-1:20 pm

Nonstop2h 20m

Boston Logan Intl

Wed 3/11

5:27 am-7:11 pm

1 stop14h 44m

$138

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 3/4

5:15 am-5:15 pm

1 stop11h 00m

Boston Logan Intl

Tue 3/10

5:27 am-7:11 pm

1 stop14h 44m

$140

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Thu 2/26

7:10 am-3:33 pm

1 stop7h 23m

Worcester

Wed 3/4

4:30 pm-8:39 pm

1 stop5h 09m

$192

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Thu 2/26

5:25 am-3:33 pm

2 stops9h 08m

Worcester

Wed 3/4

4:30 pm-8:39 pm

1 stop5h 09m

$202

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 $205.

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 O'Hare Intl Airport. 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 O'Hare Intl Airport 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 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 $211. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $292 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 $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 O'Hare Intl Airport for as low as $184 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

$86

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 $86. The best round-trip flight deal from Chicago O'Hare Intl Airport to Massachusetts found on momondo in the last 72 hours is $168.
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), 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 $61Free CancellationRating
7.2
2,895 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $79Free CancellationRating
6.3
8,444 reviews
Search Spirit Airlines flights
DeltaPriceFrom $92Free CancellationRating
7.9
8,180 reviews
Search Delta flights
American AirlinesPriceFrom $117Free CancellationRating
7.2
11,271 reviews
Search American Airlines flights
United AirlinesPriceFrom $117Free CancellationRating
7.4
9,279 reviews
Search United Airlines flights
SouthwestPriceFrom $144Free CancellationRating
8.0
4,280 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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