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Cheap flights from Chicago O'Hare Intl Airport to Massachusetts 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 Chicago O'Hare Intl Airport to Massachusetts 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.
1 adult
1 adult, Economy, 0 bags

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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.
JetBlue Logo
9:40 am - 4:10 pm
ORD
-
MVY
5h 30m
1 stop
JetBlue Logo
5:26 pm - 9:58 pm
MVY
-
ORD
5h 32m
1 stop
$158JetBlue
Tue, Jul 21 - Wed, Jul 22
JetBlue Logo
6:00 am - 3:24 pm
ORD
-
ACK
8h 24m
1 stop
JetBlue Logo
12:02 pm - 5:34 pm
ACK
-
ORD
6h 32m
1 stop
$158JetBlue
Tue, Jul 7 - Tue, Jul 14
Delta Logo
7:55 am - 11:24 am
ORD
-
BOS
2h 29mnonstop
Delta Logo
8:50 pm - 10:44 pm
BOS
-
ORD
2h 54mnonstop
$181Delta
Mon, Aug 10 - Mon, Aug 10
United Airlines Logo
9:41 pm - 1:14 am
ORD
-
BOS
2h 33mnonstop
United Airlines Logo
7:19 am - 9:17 am
BOS
-
ORD
2h 58mnonstop
$182United Airlines
Thu, Jul 2 - Tue, Jul 7
Delta Logo
7:25 pm - 11:02 pm
ORD
-
BOS
2h 37mnonstop
Delta Logo
7:30 am - 9:28 am
BOS
-
ORD
2h 58mnonstop
$187Delta
Fri, Jun 26 - Mon, Jun 29
United Airlines Logo
6:00 am - 11:16 am
ORD
-
BOS
4h 16m
1 stop
United Airlines Logo
7:19 am - 9:17 am
BOS
-
ORD
2h 58mnonstop
$188United Airlines
Tue, Jul 7 - Fri, Jul 10
American Airlines Logo
8:29 am - 4:51 pm
ORD
-
ORH
7h 22m
1 stop
American Airlines Logo
5:16 pm - 6:29 am
ORH
-
ORD
14h 13m
1 stop
$196American Airlines
Sat, Jul 4 - Fri, Jul 10
American Airlines Logo
6:29 am - 4:53 pm
ORD
-
ORH
9h 24m
1 stop
American Airlines Logo
5:18 pm - 6:56 am
ORH
-
ORD
14h 38m
1 stop
$220American Airlines
Tue, Jun 23 - Sat, Jun 27
Multiple Airlines Logo
12:20 pm - 8:20 pm
ORD
-
ALB
7h 00m
2 stops
Multiple Airlines Logo
7:53 pm - 12:15 pm
ALB
-
ORD
17h 22m
1 stop
$328Multiple Airlines
Mon, Jul 20 - Fri, Jul 24
Multiple Airlines Logo
5:22 pm - 11:59 pm
ORD
-
BDL
5h 37m
1 stop
Multiple Airlines Logo
2:10 pm - 11:29 pm
BDL
-
ORD
10h 19m
1 stop
$329Multiple Airlines
Thu, Jul 2 - Sat, Jul 4

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

Our best American Airlines deals on Chicago O'Hare Intl Airport to Massachusetts flight tickets
American Airlines
Jul 4
ORD8:29 amChicago O'Hare Intl
7h 22m
1 stop
ORH4:51 pmWorcester
Jul 10
ORH5:16 pmWorcester
14h 13m
1 stop
ORD6:29 amChicago O'Hare Intl
$196
American Airlines
Jun 20
ORD8:59 pmChicago O'Hare Intl
2h 29m
BOS12:28 amBoston Logan Intl
Jun 29
BOS7:00 amBoston Logan Intl
3h 03m
ORD9:03 amChicago O'Hare Intl
$197
American Airlines
Jul 15
ORD5:21 pmChicago O'Hare Intl
2h 39m
BOS9:00 pmBoston Logan Intl
Jul 18
BOS6:31 pmBoston Logan Intl
3h 29m
ORD9:00 pmChicago O'Hare Intl
$201

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
Aug 10
ORD7:33 amChicago O'Hare Intl
2h 32m
BOS11:05 amBoston Logan Intl
Aug 16
BOS7:05 amBoston Logan Intl
2h 58m
ORD9:03 amChicago O'Hare Intl
$181
United Airlines
Jul 2
ORD9:41 pmChicago O'Hare Intl
2h 33m
BOS1:14 amBoston Logan Intl
Jul 4
BOS8:15 amBoston Logan Intl
2h 57m
ORD10:12 amChicago O'Hare Intl
$182
United Airlines
Jul 7
ORD6:00 amChicago O'Hare Intl
4h 16m
1 stop
BOS11:16 amBoston Logan Intl
Jul 9
BOS7:19 amBoston Logan Intl
2h 58m
ORD9:17 amChicago O'Hare Intl
$188

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 June 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

Cheapest round-trip

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Tue 7/21

9:40 am-4:10 pm

1 stop5h 30m

West Tisbury Martha's Vineyard

Wed 7/22

5:26 pm-9:58 pm

1 stop5h 32m

$158

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Tue 7/7

6:00 am-3:24 pm

1 stop8h 24m

Nantucket Memorial

Tue 7/14

12:02 pm-5:34 pm

1 stop6h 32m

$158
Quickest round-trip

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 8/10

7:55 am-11:24 am

Nonstop2h 29m

Boston Logan Intl

Mon 8/10

8:50 pm-10:44 pm

Nonstop2h 54m

$181

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 7/2

9:41 pm-1:14 am

Nonstop2h 33m

Boston Logan Intl

Tue 7/7

7:19 am-9:17 am

Nonstop2h 58m

$182

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 6/26

7:25 pm-11:02 pm

Nonstop2h 37m

Boston Logan Intl

Mon 6/29

7:30 am-9:28 am

Nonstop2h 58m

$187

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 7/7

6:00 am-11:16 am

1 stop4h 16m

Boston Logan Intl

Fri 7/10

7:19 am-9:17 am

Nonstop2h 58m

$188

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Sat 7/4

8:29 am-4:51 pm

1 stop7h 22m

Worcester

Fri 7/10

5:16 pm-6:29 am

1 stop14h 13m

$196

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Tue 6/23

6:29 am-4:53 pm

1 stop9h 24m

Worcester

Sat 6/27

5:18 pm-6:56 am

1 stop14h 38m

$220

ChicagoAlbany

ORD - ALB

ORDALB

Chicago O'Hare Intl

Mon 7/20

12:20 pm-8:20 pm

2 stops7h 00m

Albany Intl

Fri 7/24

7:53 pm-12:15 pm

1 stop17h 22m

$328

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Thu 7/2

5:22 pm-11:59 pm

1 stop5h 37m

Hartford Bradley Intl

Sat 7/4

2:10 pm-11:29 pm

1 stop10h 19m

$329

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, January 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 $65. If you aren’t able to travel to Massachusetts during the month of January, then flying in December is also cheap. Prices for this month can be found on momondo for an average of $73.

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 $242. 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 $308.

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 $224. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are $299 on average. Flights to Massachusetts from Chicago O'Hare Intl Airport in the afternoon 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 from Chicago O'Hare Intl Airport 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 $241 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 $211 on momondo.

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

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

$126

Fastest flight time

1h 55m

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 $126. The best round-trip flight deal from Chicago O'Hare Intl Airport to Massachusetts found on momondo in the last 72 hours is $220.
The fastest flight from Chicago O'Hare Intl Airport to Massachusetts takes 1h 55m
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

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

  • 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 $68Free CancellationRating
7.1
2,980 reviews
Search JetBlue flights
DeltaPriceFrom $85Free CancellationRating
7.9
8,400 reviews
Search Delta flights
United AirlinesPriceFrom $126Free CancellationRating
7.4
9,804 reviews
Search United Airlines flights
American AirlinesPriceFrom $136Free CancellationRating
7.1
11,639 reviews
Search American Airlines flights
SouthwestPriceFrom $144Free CancellationRating
7.9
4,234 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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