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Cheap flights from Chicago to Massachusetts from $92

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 to Massachusetts departing on 8/11. 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

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Massachusetts

Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
9:42 am - 5:31 pm
ORD
-
BOS
6h 49m
1 stop
JetBlue Logo
4:30 pm - 9:58 pm
BOS
-
ORD
6h 28m
1 stop
$192JetBlue
Fri, Aug 14 - Fri, Aug 21
JetBlue Logo
9:42 am - 5:31 pm
ORD
-
BOS
6h 49m
1 stop
JetBlue Logo
2:45 pm - 9:58 pm
BOS
-
ORD
8h 13m
1 stop
$193JetBlue
Fri, Aug 14 - Tue, Aug 18
Southwest Logo
6:00 pm - 9:20 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
10:05 am - 11:35 am
BOS
-
MDW
2h 30mnonstop
$197Southwest
Wed, Sep 9 - Tue, Sep 15
Southwest Logo
5:30 am - 8:55 am
MDW
-
BOS
2h 25mnonstop
Southwest Logo
9:40 am - 11:15 am
BOS
-
MDW
2h 35mnonstop
$206Southwest
Fri, Oct 9 - Sat, Oct 17
American Airlines Logo
7:35 pm - 10:54 pm
ORD
-
BDL
2h 19mnonstop
American Airlines Logo
7:24 pm - 11:44 pm
BDL
-
ORD
5h 20m
1 stop
$287American Airlines
Wed, Aug 19 - Tue, Aug 25
Delta Logo
11:22 am - 11:57 pm
ORD
-
ALB
11h 35m
2 stops
Delta Logo
5:50 am - 12:59 pm
ALB
-
ORD
8h 09m
2 stops
$288Delta
Sat, Sep 5 - Tue, Sep 8
American Airlines Logo
11:15 am - 2:57 pm
ORD
-
HYA
2h 42mnonstop
American Airlines Logo
12:42 pm - 7:46 pm
HYA
-
ORD
8h 04m
1 stop
$290American Airlines
Sat, Sep 5 - Tue, Sep 8
United Airlines Logo
7:15 am - 10:38 am
ORD
-
BDL
2h 23mnonstop
United Airlines Logo
6:00 am - 7:46 am
BDL
-
ORD
2h 46mnonstop
$291United Airlines
Fri, Sep 11 - Mon, Sep 14
Delta Logo
6:42 pm - 11:51 pm
MDW
-
BDL
4h 09m
1 stop
Delta Logo
5:30 am - 9:17 am
BDL
-
MDW
4h 47m
1 stop
$297Delta
Sat, Aug 8 - Wed, Aug 12
United Airlines Logo
7:15 am - 10:24 am
ORD
-
ALB
2h 09mnonstop
United Airlines Logo
8:10 am - 9:45 am
ALB
-
ORD
2h 35mnonstop
$303United Airlines
Fri, Sep 4 - Mon, Sep 7

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JetBlue flights from Chicago to Massachusetts

Our best JetBlue deals on Chicago to Massachusetts flight tickets
JetBlue
Sep 11
ORD1:00 pmChicago O'Hare Intl
6h 49m
1 stop
BOS8:49 pmBoston Logan Intl
Sep 14
BOS6:55 amBoston Logan Intl
5h 52m
1 stop
ORD11:47 amChicago O'Hare Intl
$183
JetBlue
Aug 14
ORD9:42 amChicago O'Hare Intl
6h 49m
1 stop
BOS5:31 pmBoston Logan Intl
Aug 21
BOS4:30 pmBoston Logan Intl
6h 28m
1 stop
ORD9:58 pmChicago O'Hare Intl
$192
JetBlue
Aug 14
ORD9:42 amChicago O'Hare Intl
6h 49m
1 stop
BOS5:31 pmBoston Logan Intl
Aug 18
BOS2:45 pmBoston Logan Intl
8h 13m
1 stop
ORD9:58 pmChicago O'Hare Intl
$193

Southwest flights from Chicago to Massachusetts

Our best Southwest deals on Chicago to Massachusetts flight tickets
Southwest
Sep 9
MDW6:00 pmChicago Midway
2h 20m
BOS9:20 pmBoston Logan Intl
Sep 15
BOS10:05 amBoston Logan Intl
2h 30m
MDW11:35 amChicago Midway
$197
Southwest
Sep 11
MDW11:35 amChicago Midway
2h 20m
BOS2:55 pmBoston Logan Intl
Sep 12
BOS7:05 amBoston Logan Intl
2h 35m
MDW8:40 amChicago Midway
$206
Southwest
Sep 30
MDW6:40 amChicago Midway
2h 15m
BOS9:55 amBoston Logan Intl
Oct 6
BOS10:55 amBoston Logan Intl
2h 35m
MDW12:30 pmChicago Midway
$207

momondo Fare Finder

 
Customize your flight search to find flights from Chicago 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 July 20, 2026.
Use the filters below to find and compare flights from Chicago to Massachusetts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 8/14

9:42 am-5:31 pm

1 stop6h 49m

Boston Logan Intl

Fri 8/21

4:30 pm-9:58 pm

1 stop6h 28m

$192

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 8/14

9:42 am-5:31 pm

1 stop6h 49m

Boston Logan Intl

Tue 8/18

2:45 pm-9:58 pm

1 stop8h 13m

$193

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 9/9

6:00 pm-9:20 pm

Nonstop2h 20m

Boston Logan Intl

Tue 9/15

10:05 am-11:35 am

Nonstop2h 30m

$197

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 10/9

5:30 am-8:55 am

Nonstop2h 25m

Boston Logan Intl

Sat 10/17

9:40 am-11:15 am

Nonstop2h 35m

$206

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Wed 8/19

7:35 pm-10:54 pm

Nonstop2h 19m

Hartford Bradley Intl

Tue 8/25

7:24 pm-11:44 pm

1 stop5h 20m

$287

ChicagoAlbany

ORD - ALB

ORDALB

Chicago O'Hare Intl

Sat 9/5

11:22 am-11:57 pm

2 stops11h 35m

Albany Intl

Tue 9/8

5:50 am-12:59 pm

2 stops8h 09m

$288

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Sat 9/5

11:15 am-2:57 pm

Nonstop2h 42m

Hyannis Barnstable

Tue 9/8

12:42 pm-7:46 pm

1 stop8h 04m

$290

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Fri 9/11

7:15 am-10:38 am

Nonstop2h 23m

Hartford Bradley Intl

Mon 9/14

6:00 am-7:46 am

Nonstop2h 46m

$291

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Sat 8/8

6:42 pm-11:51 pm

1 stop4h 09m

Hartford Bradley Intl

Wed 8/12

5:30 am-9:17 am

1 stop4h 47m

$297
Quickest round-trip

ChicagoAlbany

ORD - ALB

ORDALB

Chicago O'Hare Intl

Fri 9/4

7:15 am-10:24 am

Nonstop2h 09m

Albany Intl

Mon 9/7

8:10 am-9:45 am

Nonstop2h 35m

$303

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 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 to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $199. If you aren’t able to travel to Massachusetts during the month of January, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $221.

What is the cheapest day to depart on your flight to Massachusetts?

According to our data, Saturday is the cheapest day to fly to Massachusetts from Chicago. The lowest ticket price found for a Saturday 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 because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $318.

What is the cheapest time of day to depart on your flight to Massachusetts?

Our data shows that the cheapest Chicago 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 $229. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are $300 on average. Flights to Massachusetts from Chicago in the afternoon are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Chicago to Massachusetts flight route?

Fly from Chicago O'Hare Intl to Boston Logan Intl for the best Chicago - Massachusetts flight prices

How far in advance should I book a flight from Chicago to Massachusetts?

You are more likely to see cheaper flights to Massachusetts from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around $245 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from Chicago for as low as $213 on momondo.

What cabin class options are available on Chicago to Massachusetts flights?

There are 4 cabin classes available to choose from on Chicago 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 to Massachusetts flights?

No. A direct flight is the cheapest option for a flight between Chicago to Massachusetts.

Cheap Chicago to Massachusetts flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Massachusetts

Best Price Found

$133

Fastest flight time

1h 50m

Direct flights

Every day

Airports in Massachusetts

140 airports
The best one-way flight to Massachusetts from Chicago in the past 72 hours is $133. The best round-trip flight deal from Chicago to Massachusetts found on momondo in the last 72 hours is $210.
The fastest flight from Chicago to Massachusetts takes 1h 50m
Direct flights go from Chicago to Massachusetts every day.
There are 140 airports in Massachusetts. From Chicago 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 to Massachusetts

  • When did momondo last update prices for flights from Chicago to Massachusetts?

    Prices for flights from Chicago to Massachusetts were last updated today.

  • How many operators does momondo search for flights from Chicago to Massachusetts?

  • How old do you have to be to fly from Chicago to Massachusetts?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Massachusetts.

  • What documentation or ID do you need to fly to Massachusetts?

    The travel and health documents required for your trip to Massachusetts can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Massachusetts. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Chicago to Massachusetts?

Best airlines flying from Chicago to Massachusetts

Compare and see reviews for airlines that fly from Chicago to Massachusetts with momondo
Airline
Rating
Free Cancellation
Price
JetBluePriceFrom $68Free CancellationRating
7.1
3,012 reviews
Search JetBlue flights
DeltaPriceFrom $86Free CancellationRating
7.8
8,476 reviews
Search Delta flights
SouthwestPriceFrom $114Free CancellationRating
8.0
4,241 reviews
Search Southwest flights
United AirlinesPriceFrom $127Free CancellationRating
7.4
10,014 reviews
Search United Airlines flights
American AirlinesPriceFrom $136Free CancellationRating
7.1
11,826 reviews
Search American Airlines 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?

Yes. momondo enables you to select and highlight flights to Massachusetts from Chicago with this policy.

How can momondo help me find flights from Chicago to Massachusetts?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Massachusetts.

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.

An easier way to manage your Massachusetts trip

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