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Cheap flights from Chicago O'Hare Intl Airport to Massachusetts from $44

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 9/4. 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

Southwest Logo
1:50 pm - 9:10 pmORD-BOS
6h 20m1 stop
Southwest Logo
8:15 am - 11:50 amBOS-ORD
4h 35m1 stop
$87Southwest
Find Deal
Wed, Oct 29 - Sat, Nov 1
JetBlue Logo
11:30 am - 2:46 pmORD-BOS
2h 16mnonstop
JetBlue Logo
4:55 pm - 7:05 pmBOS-ORD
3h 10mnonstop
$88JetBlue
Find Deal
Tue, Nov 4 - Tue, Nov 4
American Airlines Logo
5:36 pm - 9:00 pmORD-BOS
2h 24mnonstop
American Airlines Logo
5:00 am - 6:51 amBOS-ORD
2h 51mnonstop
$92American Airlines
Find Deal
Sat, Sep 6 - Mon, Sep 8
American Airlines Logo
8:25 pm - 11:53 pmORD-BOS
2h 28mnonstop
American Airlines Logo
5:00 am - 6:51 amBOS-ORD
2h 51mnonstop
$94American Airlines
Find Deal
Thu, Sep 4 - Mon, Sep 8
United Airlines Logo
6:30 am - 9:56 amORD-BOS
2h 26mnonstop
United Airlines Logo
6:10 am - 8:05 amBOS-ORD
2h 55mnonstop
$111United Airlines
Find Deal
Fri, Sep 5 - Mon, Sep 15
Spirit Airlines Logo
11:36 am - 11:49 pmORD-BOS
11h 13m1 stop
Spirit Airlines Logo
6:05 am - 7:07 pmBOS-ORD
14h 02m1 stop
$112Spirit Airlines
Find Deal
Wed, Aug 27 - Wed, Sep 3
Delta Logo
10:15 am - 1:48 pmORD-BOS
2h 33mnonstop
Delta Logo
11:34 am - 1:27 pmBOS-ORD
2h 53mnonstop
$117Delta
Find Deal
Wed, Sep 3 - Sat, Sep 6
United Airlines Logo
9:32 pm - 12:59 amORD-BOS
2h 27mnonstop
United Airlines Logo
6:09 am - 8:05 amBOS-ORD
2h 56mnonstop
$118United Airlines
Find Deal
Fri, Aug 15 - Fri, Aug 22
Spirit Airlines Logo
11:36 am - 11:49 pmORD-BOS
11h 13m1 stop
Spirit Airlines Logo
3:00 pm - 10:48 pmBOS-ORD
8h 48m1 stop
$125Spirit Airlines
Find Deal
Wed, Sep 3 - Wed, Sep 10
Delta Logo
7:00 am - 10:29 amORD-BOS
2h 29mnonstop
Delta Logo
3:00 pm - 7:14 pmBOS-ORD
5h 14m1 stop
$137Delta
Find Deal
Tue, Aug 19 - Wed, Aug 27

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
Nov 4
ORD11:30 amChicago O'Hare Intl
2h 16m
BOS2:46 pmBoston Logan Intl
Nov 4
BOS4:55 pmBoston Logan Intl
3h 10m
ORD7:05 pmChicago O'Hare Intl
$88
Find similar
JetBlue
Jan 24
ORD9:50 amChicago O'Hare Intl
2h 26m
BOS1:16 pmBoston Logan Intl
Jan 26
BOS7:10 amBoston Logan Intl
2h 54m
ORD9:04 amChicago O'Hare Intl
$90
Find similar
JetBlue
Sep 6
ORD9:51 amChicago O'Hare Intl
2h 29m
BOS1:20 pmBoston Logan Intl
Sep 13
BOS7:00 amBoston Logan Intl
2h 56m
ORD8:56 amChicago O'Hare Intl
$91
Find similar

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
Sep 6
ORD5:36 pmChicago O'Hare Intl
2h 24m
BOS9:00 pmBoston Logan Intl
Sep 8
BOS5:00 amBoston Logan Intl
2h 51m
ORD6:51 amChicago O'Hare Intl
$92
Find similar
American Airlines
Sep 4
ORD8:25 pmChicago O'Hare Intl
2h 28m
BOS11:53 pmBoston Logan Intl
Sep 8
BOS5:00 amBoston Logan Intl
2h 51m
ORD6:51 amChicago O'Hare Intl
$94
Find similar
American Airlines
Sep 19
ORD7:10 pmChicago O'Hare Intl
2h 30m
BOS10:40 pmBoston Logan Intl
Sep 21
BOS5:00 amBoston Logan Intl
2h 51m
ORD6:51 amChicago O'Hare Intl
$99
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 August 5, 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

Wed 10/29

1:50 pm-9:10 pm

1 stop6h 20m

Boston Logan Intl

Sat 11/1

8:15 am-11:50 am

1 stop4h 35m

$87

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 11/4

11:30 am-2:46 pm

Nonstop2h 16m

Boston Logan Intl

Tue 11/4

4:55 pm-7:05 pm

Nonstop3h 10m

$88

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 9/6

5:36 pm-9:00 pm

Nonstop2h 24m

Boston Logan Intl

Mon 9/8

5:00 am-6:51 am

Nonstop2h 51m

$92

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 9/4

8:25 pm-11:53 pm

Nonstop2h 28m

Boston Logan Intl

Mon 9/8

5:00 am-6:51 am

Nonstop2h 51m

$94

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 9/5

6:30 am-9:56 am

Nonstop2h 26m

Boston Logan Intl

Mon 9/15

6:10 am-8:05 am

Nonstop2h 55m

$111

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 8/27

11:36 am-11:49 pm

1 stop11h 13m

Boston Logan Intl

Wed 9/3

6:05 am-7:07 pm

1 stop14h 02m

$112

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/3

10:15 am-1:48 pm

Nonstop2h 33m

Boston Logan Intl

Sat 9/6

11:34 am-1:27 pm

Nonstop2h 53m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 8/15

9:32 pm-12:59 am

Nonstop2h 27m

Boston Logan Intl

Fri 8/22

6:09 am-8:05 am

Nonstop2h 56m

$118

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/3

11:36 am-11:49 pm

1 stop11h 13m

Boston Logan Intl

Wed 9/10

3:00 pm-10:48 pm

1 stop8h 48m

$125

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 8/19

7:00 am-10:29 am

Nonstop2h 29m

Boston Logan Intl

Wed 8/27

3:00 pm-7:14 pm

1 stop5h 14m

$137

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 $177. 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 $210.

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 $238. 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, Sunday 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 $212. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are $284 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 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 $182 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

$44

Fastest flight time

1h 57m

Direct flights

Every day

Airports in Massachusetts

3 airports
The best one-way flight to Massachusetts from Chicago O'Hare Intl Airport in the past 72 hours is $44. The best round-trip flight deal from Chicago O'Hare Intl Airport to Massachusetts found on momondo in the last 72 hours is $87.
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 3 airports near Massachusetts: Boston Logan Intl (BOS), 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
Spirit AirlinesPriceFrom $34Free CancellationRating
6.3
8,051 reviews
Search Spirit Airlines flights
JetBluePriceFrom $78Free CancellationRating
7.2
2,914 reviews
Search JetBlue flights
DeltaPriceFrom $91Free CancellationRating
8.0
7,985 reviews
Search Delta flights
FrontierPriceFrom $100Free CancellationRating
5.8
3,232 reviews
Search Frontier flights
American AirlinesPriceFrom $122Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $131Free CancellationRating
7.4
8,916 reviews
Search United Airlines flights
SouthwestPriceFrom $156Free CancellationRating
8.0
4,246 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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