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Cheap flights from Chicago O'Hare Intl Airport to Massachusetts from $69

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 9/30. 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

United Airlines Logo
6:30 am - 9:56 amORD-BOS
2h 26mnonstop
United Airlines Logo
3:17 pm - 5:07 pmBOS-ORD
2h 50mnonstop
$127United Airlines
Find Deal
Sat, Oct 4 - Tue, Oct 7
United Airlines Logo
6:30 am - 9:56 amORD-BOS
2h 26mnonstop
United Airlines Logo
6:00 am - 7:56 amBOS-ORD
2h 56mnonstop
$131United Airlines
Find Deal
Sun, Oct 12 - Thu, Oct 16
JetBlue Logo
6:55 pm - 10:27 pmORD-BOS
2h 32mnonstop
JetBlue Logo
3:55 pm - 5:55 pmBOS-ORD
3h 00mnonstop
$135JetBlue
Find Deal
Fri, Nov 7 - Tue, Nov 11
JetBlue Logo
8:38 pm - 12:06 amORD-BOS
2h 28mnonstop
JetBlue Logo
5:29 pm - 7:43 pmBOS-ORD
3h 14mnonstop
$137JetBlue
Find Deal
Thu, Dec 4 - Mon, Dec 8
American Airlines Logo
7:00 am - 10:20 amORD-BOS
2h 20mnonstop
American Airlines Logo
7:02 am - 9:05 amBOS-ORD
3h 03mnonstop
$138American Airlines
Find Deal
Sat, Mar 7 - Mon, Mar 9
Spirit Airlines Logo
6:00 am - 1:20 pmORD-BOS
6h 20m1 stop
Spirit Airlines Logo
3:00 pm - 1:03 amBOS-ORD
11h 03m1 stop
$139Spirit Airlines
Find Deal
Tue, Oct 28 - Wed, Oct 29
Spirit Airlines Logo
10:49 am - 12:40 amORD-BOS
12h 51m1 stop
Spirit Airlines Logo
5:45 am - 6:23 pmBOS-ORD
13h 38m1 stop
$140Spirit Airlines
Find Deal
Tue, Nov 11 - Wed, Nov 12
American Airlines Logo
8:25 pm - 11:54 pmORD-BOS
2h 29mnonstop
American Airlines Logo
8:54 am - 10:59 amBOS-ORD
3h 05mnonstop
$145American Airlines
Find Deal
Fri, Oct 24 - Tue, Oct 28
Delta Logo
3:50 pm - 7:23 pmORD-BOS
2h 33mnonstop
Delta Logo
12:55 pm - 2:49 pmBOS-ORD
2h 54mnonstop
$157Delta
Find Deal
Fri, Oct 24 - Wed, Oct 29
Delta Logo
3:50 pm - 7:23 pmORD-BOS
2h 33mnonstop
Delta Logo
4:10 pm - 6:10 pmBOS-ORD
3h 00mnonstop
$167Delta
Find Deal
Sat, Oct 11 - Tue, Oct 21

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
Oct 4
ORD6:30 amChicago O'Hare Intl
2h 26m
BOS9:56 amBoston Logan Intl
Oct 7
BOS3:17 pmBoston Logan Intl
2h 50m
ORD5:07 pmChicago O'Hare Intl
$127
Find similar
United Airlines
Oct 12
ORD6:30 amChicago O'Hare Intl
2h 26m
BOS9:56 amBoston Logan Intl
Oct 16
BOS6:00 amBoston Logan Intl
2h 56m
ORD7:56 amChicago O'Hare Intl
$131
Find similar
United Airlines
Oct 12
ORD6:30 amChicago O'Hare Intl
2h 26m
BOS9:56 amBoston Logan Intl
Oct 18
BOS6:00 amBoston Logan Intl
2h 56m
ORD7:56 amChicago O'Hare Intl
$134
Find similar

Southwest flights from Chicago O'Hare Intl Airport to Massachusetts

Our best Southwest deals on Chicago O'Hare Intl Airport to Massachusetts flight tickets
Southwest
Oct 20
ORD1:50 pmChicago O'Hare Intl
6h 10m
1 stop
BOS9:00 pmBoston Logan Intl
Oct 22
BOS5:30 amBoston Logan Intl
10h 50m
2 stops
ORD3:20 pmChicago O'Hare Intl
$142
Find similar
Southwest
Sep 30
ORD3:10 pmChicago O'Hare Intl
6h 20m
1 stop
BOS10:30 pmBoston Logan Intl
Oct 2
BOS5:35 amBoston Logan Intl
8h 10m
1 stop
ORD12:45 pmChicago O'Hare Intl
$162
Find similar
Southwest
Oct 4
ORD1:30 pmChicago O'Hare Intl
4h 20m
1 stop
BOS6:50 pmBoston Logan Intl
Oct 5
BOS5:35 amBoston Logan Intl
7h 15m
1 stop
ORD11:50 amChicago O'Hare Intl
$207
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 September 24, 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 10/4

6:30 am-9:56 am

Nonstop2h 26m

Boston Logan Intl

Tue 10/7

3:17 pm-5:07 pm

Nonstop2h 50m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 10/12

6:30 am-9:56 am

Nonstop2h 26m

Boston Logan Intl

Thu 10/16

6:00 am-7:56 am

Nonstop2h 56m

$131

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 11/7

6:55 pm-10:27 pm

Nonstop2h 32m

Boston Logan Intl

Tue 11/11

3:55 pm-5:55 pm

Nonstop3h 00m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 12/4

8:38 pm-12:06 am

Nonstop2h 28m

Boston Logan Intl

Mon 12/8

5:29 pm-7:43 pm

Nonstop3h 14m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 3/7

7:00 am-10:20 am

Nonstop2h 20m

Boston Logan Intl

Mon 3/9

7:02 am-9:05 am

Nonstop3h 03m

$138

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 10/28

6:00 am-1:20 pm

1 stop6h 20m

Boston Logan Intl

Wed 10/29

3:00 pm-1:03 am

1 stop11h 03m

$139

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 11/11

10:49 am-12:40 am

1 stop12h 51m

Boston Logan Intl

Wed 11/12

5:45 am-6:23 pm

1 stop13h 38m

$140

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 10/24

8:25 pm-11:54 pm

Nonstop2h 29m

Boston Logan Intl

Tue 10/28

8:54 am-10:59 am

Nonstop3h 05m

$145

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 10/24

3:50 pm-7:23 pm

Nonstop2h 33m

Boston Logan Intl

Wed 10/29

12:55 pm-2:49 pm

Nonstop2h 54m

$157

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 10/11

3:50 pm-7:23 pm

Nonstop2h 33m

Boston Logan Intl

Tue 10/21

4:10 pm-6:10 pm

Nonstop3h 00m

$167

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 $197. 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 $209.

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 $243. 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 $309.

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 $225. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $302 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 $235 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 $190 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

$100

Fastest flight time

2h 01m

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 $100. The best round-trip flight deal from Chicago O'Hare Intl Airport to Massachusetts found on momondo in the last 72 hours is $167.
The fastest flight from Chicago O'Hare Intl Airport to Massachusetts takes 2h 01m
Direct flights go from Chicago O'Hare Intl Airport to Massachusetts every day.
There are 3 airports near Massachusetts: 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
Spirit AirlinesPriceFrom $46Free CancellationRating
6.3
8,042 reviews
Search Spirit Airlines flights
JetBluePriceFrom $78Free CancellationRating
7.2
2,911 reviews
Search JetBlue flights
DeltaPriceFrom $96Free CancellationRating
7.9
7,973 reviews
Search Delta flights
FrontierPriceFrom $100Free CancellationRating
5.8
3,163 reviews
Search Frontier flights
American AirlinesPriceFrom $118Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $127Free CancellationRating
7.4
8,928 reviews
Search United Airlines flights
SouthwestPriceFrom $156Free CancellationRating
8.0
4,244 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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