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Cheap flights from Chicago to Massachusetts from $59

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 12/3. 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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0 bags

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Find the cheapest flights from Chicago to Massachusetts

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
7:10 pm - 10:34 pmORD-BOS
2h 24mnonstop
Delta Logo
4:20 pm - 6:16 pmBOS-ORD
2h 56mnonstop
$117Delta
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Wed, Dec 10 - Sat, Dec 13
Southwest Logo
1:40 pm - 4:55 pmMDW-BOS
2h 15mnonstop
Southwest Logo
1:35 pm - 3:20 pmBOS-MDW
2h 45mnonstop
$117Southwest
Find Deal
Thu, Nov 27 - Wed, Dec 3
Delta Logo
7:10 am - 10:36 amORD-BOS
2h 26mnonstop
Delta Logo
4:05 pm - 6:02 pmBOS-ORD
2h 57mnonstop
$118Delta
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Thu, Dec 4 - Sun, Dec 7
JetBlue Logo
6:55 pm - 10:27 pmORD-BOS
2h 32mnonstop
JetBlue Logo
8:30 am - 10:35 amBOS-ORD
3h 05mnonstop
$120JetBlue
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Fri, Nov 14 - Tue, Nov 18
JetBlue Logo
8:45 pm - 12:13 amORD-BOS
2h 28mnonstop
JetBlue Logo
8:30 am - 10:35 amBOS-ORD
3h 05mnonstop
$122JetBlue
Find Deal
Wed, Nov 26 - Sat, Dec 6
United Airlines Logo
12:50 pm - 4:10 pmORD-BOS
2h 20mnonstop
United Airlines Logo
6:00 am - 8:00 amBOS-ORD
3h 00mnonstop
$132United Airlines
Find Deal
Wed, Nov 26 - Wed, Dec 3
United Airlines Logo
9:12 pm - 12:45 amORD-BOS
2h 33mnonstop
United Airlines Logo
4:16 pm - 6:16 pmBOS-ORD
3h 00mnonstop
$134United Airlines
Find Deal
Sun, Dec 21 - Sat, Jan 10
American Airlines Logo
7:00 am - 10:25 amORD-BOS
2h 25mnonstop
American Airlines Logo
7:02 am - 9:05 amBOS-ORD
3h 03mnonstop
$138American Airlines
Find Deal
Sat, Mar 7 - Mon, Mar 9
American Airlines Logo
1:04 pm - 4:32 pmORD-BOS
2h 28mnonstop
American Airlines Logo
6:45 am - 8:52 amBOS-ORD
3h 07mnonstop
$150American Airlines
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Thu, Nov 13 - Sun, Nov 16
Spirit Airlines Logo
3:26 pm - 11:56 pmORD-BOS
7h 30m1 stop
Spirit Airlines Logo
12:29 pm - 7:02 pmBOS-ORD
7h 33m1 stop
$163Spirit Airlines
Find Deal
Sat, Dec 6 - Wed, Dec 31

Delta flights from Chicago to Massachusetts

Our best Delta deals on Chicago to Massachusetts flight tickets
Delta
Dec 10
ORD7:10 pmChicago O'Hare Intl
2h 24m
BOS10:34 pmBoston Logan Intl
Dec 13
BOS4:20 pmBoston Logan Intl
2h 56m
ORD6:16 pmChicago O'Hare Intl
$117
Find similar
Delta
Dec 4
ORD7:10 amChicago O'Hare Intl
2h 26m
BOS10:36 amBoston Logan Intl
Dec 7
BOS4:05 pmBoston Logan Intl
2h 57m
ORD6:02 pmChicago O'Hare Intl
$118
Find similar
Delta
Nov 24
ORD7:10 amChicago O'Hare Intl
2h 25m
BOS10:35 amBoston Logan Intl
Dec 4
BOS4:05 pmBoston Logan Intl
2h 57m
ORD6:02 pmChicago O'Hare Intl
$127
Find similar

Southwest flights from Chicago to Massachusetts

Our best Southwest deals on Chicago to Massachusetts flight tickets
Southwest
Nov 27
MDW1:40 pmChicago Midway
2h 15m
BOS4:55 pmBoston Logan Intl
Dec 3
BOS1:35 pmBoston Logan Intl
2h 45m
MDW3:20 pmChicago Midway
$117
Find similar
Southwest
Dec 24
MDW6:15 pmChicago Midway
2h 20m
BOS9:35 pmBoston Logan Intl
Dec 28
BOS5:15 amBoston Logan Intl
2h 45m
MDW7:00 amChicago Midway
$124
Find similar
Southwest
Dec 4
MDW6:15 pmChicago Midway
2h 20m
BOS9:35 pmBoston Logan Intl
Dec 9
BOS6:00 pmBoston Logan Intl
5h 35m
1 stop
MDW10:35 pmChicago Midway
$127
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 November 3, 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

Wed 12/10

7:10 pm-10:34 pm

Nonstop2h 24m

Boston Logan Intl

Sat 12/13

4:20 pm-6:16 pm

Nonstop2h 56m

$117

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 11/27

1:40 pm-4:55 pm

Nonstop2h 15m

Boston Logan Intl

Wed 12/3

1:35 pm-3:20 pm

Nonstop2h 45m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 12/4

7:10 am-10:36 am

Nonstop2h 26m

Boston Logan Intl

Sun 12/7

4:05 pm-6:02 pm

Nonstop2h 57m

$118

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 11/14

6:55 pm-10:27 pm

Nonstop2h 32m

Boston Logan Intl

Tue 11/18

8:30 am-10:35 am

Nonstop3h 05m

$120

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 11/26

8:45 pm-12:13 am

Nonstop2h 28m

Boston Logan Intl

Sat 12/6

8:30 am-10:35 am

Nonstop3h 05m

$122

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 11/26

12:50 pm-4:10 pm

Nonstop2h 20m

Boston Logan Intl

Wed 12/3

6:00 am-8:00 am

Nonstop3h 00m

$132

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 12/21

9:12 pm-12:45 am

Nonstop2h 33m

Boston Logan Intl

Sat 1/10

4:16 pm-6:16 pm

Nonstop3h 00m

$134

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 3/7

7:00 am-10:25 am

Nonstop2h 25m

Boston Logan Intl

Mon 3/9

7:02 am-9:05 am

Nonstop3h 03m

$138

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 11/13

1:04 pm-4:32 pm

Nonstop2h 28m

Boston Logan Intl

Sun 11/16

6:45 am-8:52 am

Nonstop3h 07m

$150

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 12/6

3:26 pm-11:56 pm

1 stop7h 30m

Boston Logan Intl

Wed 12/31

12:29 pm-7:02 pm

1 stop7h 33m

$163

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 $317.

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 $218. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $308 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 O'Hare Intl 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 $188 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

$93

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 $93. The best round-trip flight deal from Chicago to Massachusetts found on momondo in the last 72 hours is $150.
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 $68Free CancellationRating
6.3
8,114 reviews
Search Spirit Airlines flights
JetBluePriceFrom $76Free CancellationRating
7.2
2,907 reviews
Search JetBlue flights
DeltaPriceFrom $102Free CancellationRating
7.9
8,001 reviews
Search Delta flights
FrontierPriceFrom $104Free CancellationRating
5.8
3,117 reviews
Search Frontier flights
American AirlinesPriceFrom $117Free CancellationRating
7.2
11,036 reviews
Search American Airlines flights
United AirlinesPriceFrom $118Free CancellationRating
7.4
8,997 reviews
Search United Airlines flights
SouthwestPriceFrom $137Free CancellationRating
8.0
4,238 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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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