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Cheap flights from Massachusetts to Chicago from $60

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Massachusetts to Chicago departing on 3/3. 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 Massachusetts to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
7:15 am - 9:10 am
BOS
-
MDW
2h 55mnonstop
Southwest Logo
3:30 pm - 6:45 pm
MDW
-
BOS
2h 15mnonstop
$132Southwest
Wed, Apr 1 - Fri, Apr 3
Multiple Airlines Logo
7:00 am - 9:10 am
BOS
-
ORD
3h 10mnonstop
Multiple Airlines Logo
6:02 pm - 1:13 am
ORD
-
BOS
6h 11m
1 stop
$132Multiple Airlines
Wed, Feb 18 - Tue, Feb 24
United Airlines Logo
6:28 pm - 8:30 pm
BOS
-
ORD
3h 02mnonstop
United Airlines Logo
6:05 pm - 9:28 pm
ORD
-
BOS
2h 23mnonstop
$134United Airlines
Mon, Mar 2 - Mon, Mar 9
American Airlines Logo
7:00 am - 9:05 am
BOS
-
ORD
3h 05mnonstop
American Airlines Logo
8:45 pm - 11:59 pm
ORD
-
BOS
2h 14mnonstop
$135American Airlines
Wed, Feb 11 - Sat, Feb 14
American Airlines Logo
6:52 am - 9:03 am
BOS
-
ORD
3h 11mnonstop
American Airlines Logo
7:40 pm - 11:01 pm
ORD
-
BOS
2h 21mnonstop
$136American Airlines
Thu, Feb 26 - Mon, Mar 2
JetBlue Logo
2:50 pm - 4:55 pm
BOS
-
ORD
3h 05mnonstop
JetBlue Logo
10:00 am - 1:20 pm
ORD
-
BOS
2h 20mnonstop
$137JetBlue
Wed, Feb 11 - Thu, Feb 12
Delta Logo
3:35 pm - 10:31 pm
BOS
-
MDW
7h 56m
1 stop
Delta Logo
6:20 pm - 11:26 pm
MDW
-
BOS
4h 06m
1 stop
$139Delta
Mon, Mar 2 - Wed, Mar 4
Delta Logo
6:45 pm - 11:56 pm
BOS
-
ORD
6h 11m
1 stop
Delta Logo
10:36 am - 6:21 pm
ORD
-
BOS
6h 45m
1 stop
$139Delta
Mon, Mar 2 - Wed, Mar 4
United Airlines Logo
7:45 am - 9:50 am
BOS
-
ORD
3h 05mnonstop
United Airlines Logo
7:30 am - 10:49 am
ORD
-
BOS
2h 19mnonstop
$140United Airlines
Wed, Feb 25 - Sun, Mar 1
JetBlue Logo
6:10 am - 11:54 am
BOS
-
ORD
6h 44m
1 stop
JetBlue Logo
10:00 am - 1:20 pm
ORD
-
BOS
2h 20mnonstop
$141JetBlue
Thu, Feb 26 - Tue, Mar 3

JetBlue flights from Massachusetts to Chicago

Our best JetBlue deals on Massachusetts to Chicago flight tickets
JetBlue
Feb 11
BOS2:50 pmBoston Logan Intl
3h 05m
ORD4:55 pmChicago O'Hare Intl
Feb 18
ORD10:00 amChicago O'Hare Intl
2h 20m
BOS1:20 pmBoston Logan Intl
$133
JetBlue
Feb 4
BOS3:35 pmBoston Logan Intl
3h 08m
ORD5:43 pmChicago O'Hare Intl
Feb 5
ORD7:40 amChicago O'Hare Intl
2h 25m
BOS11:05 amBoston Logan Intl
$134
JetBlue
Feb 28
BOS7:00 amBoston Logan Intl
3h 10m
ORD9:10 amChicago O'Hare Intl
Mar 1
ORD7:30 amChicago O'Hare Intl
2h 19m
BOS10:49 amBoston Logan Intl
$137

Frontier flights from Massachusetts to Chicago

Our best Frontier deals on Massachusetts to Chicago flight tickets
Frontier
Feb 25
BOS6:00 amBoston Logan Intl
11h 52m
1 stop
ORD4:52 pmChicago O'Hare Intl
Feb 26
ORD4:42 pmChicago O'Hare Intl
7h 31m
1 stop
BOS1:13 amBoston Logan Intl
$138
Frontier
Feb 28
BOS6:00 amBoston Logan Intl
17h 39m
1 stop
ORD10:39 pmChicago O'Hare Intl
Mar 2
ORD4:42 pmChicago O'Hare Intl
7h 31m
1 stop
BOS1:13 amBoston Logan Intl
$143
Frontier
Mar 2
BOS6:00 amBoston Logan Intl
29h 51m
1 stop
ORD10:51 amChicago O'Hare Intl
Mar 4
ORD6:02 pmChicago O'Hare Intl
15h 48m
2 stops
BOS10:50 amBoston Logan Intl
$145

momondo Fare Finder

 
Customize your flight search to find flights from Massachusetts to Chicago 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 February 1, 2026.
Use the filters below to find and compare flights from Massachusetts to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 4/1

7:15 am-9:10 am

Nonstop2h 55m

Chicago Midway

Fri 4/3

3:30 pm-6:45 pm

Nonstop2h 15m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 2/18

7:00 am-9:10 am

Nonstop3h 10m

Chicago O'Hare Intl

Tue 2/24

6:02 pm-1:13 am

1 stop6h 11m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 3/2

6:28 pm-8:30 pm

Nonstop3h 02m

Chicago O'Hare Intl

Mon 3/9

6:05 pm-9:28 pm

Nonstop2h 23m

$134

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 2/11

7:00 am-9:05 am

Nonstop3h 05m

Chicago O'Hare Intl

Sat 2/14

8:45 pm-11:59 pm

Nonstop2h 14m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 2/26

6:52 am-9:03 am

Nonstop3h 11m

Chicago O'Hare Intl

Mon 3/2

7:40 pm-11:01 pm

Nonstop2h 21m

$136

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 2/11

2:50 pm-4:55 pm

Nonstop3h 05m

Chicago O'Hare Intl

Thu 2/12

10:00 am-1:20 pm

Nonstop2h 20m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 3/2

3:35 pm-10:31 pm

1 stop7h 56m

Chicago Midway

Wed 3/4

6:20 pm-11:26 pm

1 stop4h 06m

$139

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 3/2

6:45 pm-11:56 pm

1 stop6h 11m

Chicago O'Hare Intl

Wed 3/4

10:36 am-6:21 pm

1 stop6h 45m

$139

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 2/25

7:45 am-9:50 am

Nonstop3h 05m

Chicago O'Hare Intl

Sun 3/1

7:30 am-10:49 am

Nonstop2h 19m

$140

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 2/26

6:10 am-11:54 am

1 stop6h 44m

Chicago O'Hare Intl

Tue 3/3

10:00 am-1:20 pm

Nonstop2h 20m

$141

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 Chicago from

How to get the cheapest flight ticket from Massachusetts to Chicago

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 Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Massachusetts, with most prices found around $187. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Massachusetts to Chicago during January average around $207.

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

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $308. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Massachusetts to Chicago for around $406.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Massachusetts to Chicago during this time can be as low as $271. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $364.

What is the cheapest Massachusetts to Chicago flight route?

Fly from Boston Logan Intl to Chicago Midway for the best Massachusetts - Chicago flight prices

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

You are more likely to see cheaper flights to Chicago from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $248 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Massachusetts for as low as $217 on momondo.

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

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

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

Cheap Massachusetts to Chicago flight deals and tips

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

Best Price Found

$109

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Massachusetts in the past 72 hours is $109. The best round-trip flight deal from Massachusetts to Chicago found on momondo in the last 72 hours is $213.
The fastest flight from Massachusetts to Chicago takes 2h 10m
Direct flights go from Massachusetts to Chicago every day.
There are 3 airports in Chicago. From Massachusetts there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

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

    Prices for flights from Massachusetts to Chicago are updated daily.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Massachusetts to Chicago.

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

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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

Best airlines flying from Massachusetts to Chicago

Compare and see reviews for airlines that fly from Massachusetts to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $45Free CancellationRating
6.3
8,393 reviews
Search Spirit Airlines flights
JetBluePriceFrom $68Free CancellationRating
7.2
2,891 reviews
Search JetBlue flights
DeltaPriceFrom $80Free CancellationRating
7.9
8,128 reviews
Search Delta flights
SouthwestPriceFrom $117Free CancellationRating
8.0
4,272 reviews
Search Southwest flights
United AirlinesPriceFrom $117Free CancellationRating
7.4
9,226 reviews
Search United Airlines flights
American AirlinesPriceFrom $128Free CancellationRating
7.2
11,211 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Massachusetts to Chicago?

It is quick and easy to find Massachusetts to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Massachusetts to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Massachusetts which offer a flexible booking policy as well as other useful filters and features.

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

Once all potential Massachusetts to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Massachusetts to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Massachusetts to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport