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Cheap flights from Chicago O'Hare Intl Airport to Massachusetts from $70

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 4/20. 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.
JetBlue Logo
6:00 am - 9:15 am
ORD
-
BOS
2h 15mnonstop
JetBlue Logo
7:02 am - 8:59 am
BOS
-
ORD
2h 57mnonstop
$137JetBlue
Thu, Apr 30 - Sun, May 3
Frontier Logo
6:08 pm - 1:31 am
ORD
-
BOS
6h 23m
1 stop
Frontier Logo
9:18 am - 7:51 pm
BOS
-
ORD
11h 33m
1 stop
$140Frontier
Wed, Apr 29 - Tue, May 12
Multiple Airlines Logo
11:28 am - 11:45 am
ORD
-
BOS
23h 17m
1 stop
Multiple Airlines Logo
6:00 am - 5:00 pm
BOS
-
ORD
12h 00m
1 stop
$146Multiple Airlines
Mon, Apr 20 - Wed, Apr 22
Multiple Airlines Logo
11:28 am - 11:45 am
ORD
-
BOS
23h 17m
1 stop
Multiple Airlines Logo
12:31 pm - 11:01 pm
BOS
-
ORD
11h 30m
1 stop
$147Multiple Airlines
Mon, Apr 20 - Mon, Apr 27
Multiple Airlines Logo
11:28 am - 1:31 am
ORD
-
BOS
13h 03m
1 stop
Multiple Airlines Logo
12:52 pm - 10:23 am
BOS
-
ORD
22h 31m
1 stop
$148Multiple Airlines
Tue, Apr 21 - Tue, Apr 28
Multiple Airlines Logo
6:08 pm - 1:31 am
ORD
-
BOS
6h 23m
1 stop
Multiple Airlines Logo
7:35 pm - 9:39 pm
BOS
-
ORD
3h 04mnonstop
$149Multiple Airlines
Tue, Apr 21 - Wed, Apr 22
Delta Logo
9:35 am - 4:43 pm
ORD
-
ORH
6h 08m
1 stop
Delta Logo
5:24 pm - 10:15 pm
ORH
-
ORD
5h 51m
1 stop
$192Delta
Thu, Apr 30 - Mon, May 4
Delta Logo
5:15 am - 4:43 pm
ORD
-
ORH
10h 28m
2 stops
Delta Logo
5:24 pm - 10:19 pm
ORH
-
ORD
5h 55m
1 stop
$202Delta
Wed, Apr 29 - Wed, May 6
American Airlines Logo
5:00 am - 2:14 pm
ORD
-
ORH
8h 14m
2 stops
American Airlines Logo
2:39 pm - 11:54 pm
ORH
-
ORD
10h 15m
2 stops
$208American Airlines
Wed, Apr 29 - Wed, May 6
American Airlines Logo
7:00 am - 2:02 pm
ORD
-
ACK
6h 02m
1 stop
American Airlines Logo
12:16 pm - 2:24 pm
ACK
-
ORD
3h 08mnonstop
$272American Airlines
Sat, Jun 13 - Sat, Jun 20

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
Apr 11
ORD8:58 amChicago O'Hare Intl
2h 30m
BOS12:28 pmBoston Logan Intl
Apr 12
BOS6:05 amBoston Logan Intl
3h 03m
ORD8:08 amChicago O'Hare Intl
$137
JetBlue
May 2
ORD6:00 amChicago O'Hare Intl
2h 15m
BOS9:15 amBoston Logan Intl
May 3
BOS7:02 amBoston Logan Intl
2h 57m
ORD8:59 amChicago O'Hare Intl
$150
JetBlue
May 2
ORD6:00 amChicago O'Hare Intl
2h 15m
BOS9:15 amBoston Logan Intl
May 3
BOS7:02 amBoston Logan Intl
2h 57m
ORD8:59 amChicago O'Hare Intl
$151

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

Our best Spirit Airlines deals on Chicago O'Hare Intl Airport to Massachusetts flight tickets
Spirit Airlines
Apr 20
ORD7:15 pmChicago O'Hare Intl
14h 00m
1 stop
BOS10:15 amBoston Logan Intl
Apr 22
BOS8:16 pmBoston Logan Intl
14h 20m
1 stop
ORD9:36 amChicago O'Hare Intl
$168
Spirit Airlines
Apr 18
ORD7:15 pmChicago O'Hare Intl
14h 00m
1 stop
BOS10:15 amBoston Logan Intl
Apr 22
BOS8:16 pmBoston Logan Intl
14h 20m
1 stop
ORD9:36 amChicago O'Hare Intl
$173
Spirit Airlines
Apr 11
ORD5:05 amChicago O'Hare Intl
9h 23m
1 stop
BOS3:28 pmBoston Logan Intl
Apr 14
BOS5:45 amBoston Logan Intl
12h 30m
1 stop
ORD5:15 pmChicago O'Hare Intl
$178

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 April 2, 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
Quickest round-trip

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 4/30

6:00 am-9:15 am

Nonstop2h 15m

Boston Logan Intl

Sun 5/3

7:02 am-8:59 am

Nonstop2h 57m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 4/29

6:08 pm-1:31 am

1 stop6h 23m

Boston Logan Intl

Tue 5/12

9:18 am-7:51 pm

1 stop11h 33m

$140

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 4/20

11:28 am-11:45 am

1 stop23h 17m

Boston Logan Intl

Wed 4/22

6:00 am-5:00 pm

1 stop12h 00m

$146

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 4/20

11:28 am-11:45 am

1 stop23h 17m

Boston Logan Intl

Mon 4/27

12:31 pm-11:01 pm

1 stop11h 30m

$147

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 4/21

11:28 am-1:31 am

1 stop13h 03m

Boston Logan Intl

Tue 4/28

12:52 pm-10:23 am

1 stop22h 31m

$148

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 4/21

6:08 pm-1:31 am

1 stop6h 23m

Boston Logan Intl

Wed 4/22

7:35 pm-9:39 pm

Nonstop3h 04m

$149

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Thu 4/30

9:35 am-4:43 pm

1 stop6h 08m

Worcester

Mon 5/4

5:24 pm-10:15 pm

1 stop5h 51m

$192

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Wed 4/29

5:15 am-4:43 pm

2 stops10h 28m

Worcester

Wed 5/6

5:24 pm-10:19 pm

1 stop5h 55m

$202

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Wed 4/29

5:00 am-2:14 pm

2 stops8h 14m

Worcester

Wed 5/6

2:39 pm-11:54 pm

2 stops10h 15m

$208

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Sat 6/13

7:00 am-2:02 pm

1 stop6h 02m

Nantucket Memorial

Sat 6/20

12:16 pm-2:24 pm

Nonstop3h 08m

$272

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 $194. 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 $231. 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 $293.

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 $209. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $287 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 $192 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

$137

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 $137. The best round-trip flight deal from Chicago O'Hare Intl Airport to Massachusetts found on momondo in the last 72 hours is $183.
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

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 $62Free CancellationRating
7.2
2,915 reviews
Search JetBlue flights
DeltaPriceFrom $87Free CancellationRating
7.9
8,373 reviews
Search Delta flights
Spirit AirlinesPriceFrom $91Free CancellationRating
6.3
8,579 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $117Free CancellationRating
7.1
11,553 reviews
Search American Airlines flights
United AirlinesPriceFrom $117Free CancellationRating
7.4
9,537 reviews
Search United Airlines flights
SouthwestPriceFrom $144Free CancellationRating
8.0
4,341 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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