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Cheap flights from Chicago 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 to Massachusetts departing on 9/23. 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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Cheap round-trip flights

JetBlue Logo
7:50 pm - 11:25 pmORD-BOS
2h 35mnonstop
JetBlue Logo
7:00 am - 8:56 amBOS-ORD
2h 56mnonstop
$127JetBlue
Find Deal
lun., sep. 29 - sáb., oct. 4
Southwest Logo
12:40 pm - 6:00 pmMDW-BOS
4h 20m1 stop
Southwest Logo
10:25 am - 12:10 pmBOS-MDW
2h 45mnonstop
$127Southwest
Find Deal
mar., oct. 21 - jue., oct. 23
United Airlines Logo
9:25 pm - 12:45 amORD-BOS
2h 20mnonstop
United Airlines Logo
6:23 pm - 8:23 pmBOS-ORD
3h 00mnonstop
$133United Airlines
Find Deal
vie., nov. 7 - lun., nov. 10
Spirit Airlines Logo
6:00 am - 1:20 pmORD-BOS
6h 20m1 stop
Spirit Airlines Logo
6:16 am - 11:45 pmBOS-ORD
18h 29m1 stop
$136Spirit Airlines
Find Deal
mié., oct. 8 - mié., oct. 15
United Airlines Logo
9:25 pm - 12:45 amORD-BOS
2h 20mnonstop
United Airlines Logo
6:26 pm - 8:25 pmBOS-ORD
2h 59mnonstop
$138United Airlines
Find Deal
jue., oct. 30 - sáb., nov. 1
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
mar., oct. 28 - mar., oct. 28
Delta Logo
7:10 pm - 10:45 pmORD-BOS
2h 35mnonstop
Delta Logo
7:20 am - 9:22 amBOS-ORD
3h 02mnonstop
$147Delta
Find Deal
vie., oct. 17 - sáb., oct. 25
American Airlines Logo
7:00 am - 3:59 pmORD-ORH
7h 59m1 stop
American Airlines Logo
4:24 pm - 8:43 pmORH-ORD
5h 19m1 stop
$154American Airlines
Find Deal
mar., sep. 30 - sáb., oct. 4
Delta Logo
7:10 am - 10:36 amORD-BOS
2h 26mnonstop
Delta Logo
4:05 pm - 6:05 pmBOS-ORD
3h 00mnonstop
$157Delta
Find Deal
lun., nov. 24 - mar., dic. 2
American Airlines Logo
7:32 pm - 11:02 pmORD-BOS
2h 30mnonstop
American Airlines Logo
5:24 am - 7:25 amBOS-ORD
3h 01mnonstop
$162American Airlines
Find Deal
sáb., oct. 18 - dom., oct. 26

American Airlines flights from Chicago to Massachusetts

Our best American Airlines deals on Chicago to Massachusetts flight tickets
American Airlines
Sep 28
ORD6:05 amChicago O'Hare Intl
2h 27m
BOS9:32 amBoston Logan Intl
Oct 4
BOS8:35 amBoston Logan Intl
2h 57m
ORD10:32 amChicago O'Hare Intl
$147
Find similar
American Airlines
Sep 30
ORD7:00 amChicago O'Hare Intl
7h 59m
1 stop
ORH3:59 pmWorcester
Oct 4
ORH4:24 pmWorcester
5h 19m
1 stop
ORD8:43 pmChicago O'Hare Intl
$154
Find similar
American Airlines
Oct 18
ORD7:32 pmChicago O'Hare Intl
2h 30m
BOS11:02 pmBoston Logan Intl
Oct 26
BOS5:24 amBoston Logan Intl
3h 01m
ORD7:25 amChicago O'Hare Intl
$162
Find similar

JetBlue flights from Chicago to Massachusetts

Our best JetBlue deals on Chicago to Massachusetts flight tickets
JetBlue
Sep 29
ORD7:50 pmChicago O'Hare Intl
2h 35m
BOS11:25 pmBoston Logan Intl
Oct 4
BOS7:00 amBoston Logan Intl
2h 56m
ORD8:56 amChicago O'Hare Intl
$127
Find similar
JetBlue
Oct 1
ORD9:51 amChicago O'Hare Intl
2h 29m
BOS1:20 pmBoston Logan Intl
Oct 1
BOS4:40 pmBoston Logan Intl
3h 15m
ORD6:55 pmChicago O'Hare Intl
$130
Find similar
JetBlue
Oct 1
ORD9:51 amChicago O'Hare Intl
2h 29m
BOS1:20 pmBoston Logan Intl
Oct 15
BOS7:09 amBoston Logan Intl
3h 13m
ORD9:22 amChicago O'Hare Intl
$135
Find similar

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 septiembre 17, 2025.
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

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

lun. 9/29

7:50 pm-11:25 pm

Nonstop2h 35m

Boston Logan Intl

sáb. 10/4

7:00 am-8:56 am

Nonstop2h 56m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

mar. 10/21

12:40 pm-6:00 pm

1 stop4h 20m

Boston Logan Intl

jue. 10/23

10:25 am-12:10 pm

Nonstop2h 45m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

vie. 11/7

9:25 pm-12:45 am

Nonstop2h 20m

Boston Logan Intl

lun. 11/10

6:23 pm-8:23 pm

Nonstop3h 00m

$133

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mié. 10/8

6:00 am-1:20 pm

1 stop6h 20m

Boston Logan Intl

mié. 10/15

6:16 am-11:45 pm

1 stop18h 29m

$136

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 10/30

9:25 pm-12:45 am

Nonstop2h 20m

Boston Logan Intl

sáb. 11/1

6:26 pm-8:25 pm

Nonstop2h 59m

$138

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mar. 10/28

6:00 am-1:20 pm

1 stop6h 20m

Boston Logan Intl

mar. 10/28

3:00 pm-1:03 am

1 stop11h 03m

$139

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

vie. 10/17

7:10 pm-10:45 pm

Nonstop2h 35m

Boston Logan Intl

sáb. 10/25

7:20 am-9:22 am

Nonstop3h 02m

$147

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

mar. 9/30

7:00 am-3:59 pm

1 stop7h 59m

Worcester

sáb. 10/4

4:24 pm-8:43 pm

1 stop5h 19m

$154

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

lun. 11/24

7:10 am-10:36 am

Nonstop2h 26m

Boston Logan Intl

mar. 12/2

4:05 pm-6:05 pm

Nonstop3h 00m

$157

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 10/18

7:32 pm-11:02 pm

Nonstop2h 30m

Boston Logan Intl

dom. 10/26

5:24 am-7:25 am

Nonstop3h 01m

$162

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, September 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 $207. 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 $217.

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. 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 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 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 $299 on average. Flights to Massachusetts from Chicago at noon 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 Midway to Boston Logan Intl for the best Chicago - 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 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 for as low as $190 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

$68

Fastest flight time

1h 50m

Direct flights

Every day

Airports in Massachusetts

2 airports
The best one-way flight to Massachusetts from Chicago in the past 72 hours is $68. The best round-trip flight deal from Chicago to Massachusetts found on momondo in the last 72 hours is $168.
The fastest flight from Chicago to Massachusetts takes 1h 50m
Direct flights go from Chicago to Massachusetts every day.
There are 2 airports near Massachusetts: Albany Intl (ALB), Hartford Bradley Intl (BDL)
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  • 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
Spirit AirlinesPriceFrom $37Free CancellationRating
6.3
8,023 reviews
Search Spirit Airlines flights
JetBluePriceFrom $78Free CancellationRating
7.2
2,914 reviews
Search JetBlue flights
DeltaPriceFrom $95Free CancellationRating
7.9
7,961 reviews
Search Delta flights
FrontierPriceFrom $100Free CancellationRating
5.8
3,173 reviews
Search Frontier flights
American AirlinesPriceFrom $118Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $132Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
SouthwestPriceFrom $141Free CancellationRating
8.0
4,242 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?

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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1 adult
vie. 10/17
vie. 10/24
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