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Cheap flights from Massachusetts to Chicago from $68

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 2/20. 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
3:45 pm - 5:30 pm
BOS
-
MDW
2h 45mnonstop
Southwest Logo
7:00 pm - 10:20 pm
MDW
-
BOS
2h 20mnonstop
$132Southwest
Fri, May 1 - Mon, May 4
Southwest Logo
5:30 am - 7:20 am
BOS
-
MDW
2h 50mnonstop
Southwest Logo
7:40 am - 10:55 am
MDW
-
BOS
2h 15mnonstop
$133Southwest
Wed, Mar 4 - Sat, Mar 7
Southwest Logo
2:10 pm - 7:25 pm
BOS
-
MDW
6h 15m
1 stop
Southwest Logo
6:35 pm - 9:50 pm
MDW
-
BOS
2h 15mnonstop
$134Southwest
Sat, Feb 28 - Mon, Mar 2
Southwest Logo
6:25 pm - 8:25 pm
BOS
-
MDW
3h 00mnonstop
Southwest Logo
3:30 pm - 6:45 pm
MDW
-
BOS
2h 15mnonstop
$137Southwest
Mon, Mar 9 - Thu, Mar 12
Southwest Logo
9:00 am - 4:20 pm
BOS
-
MDW
8h 20m
2 stops
Southwest Logo
6:35 pm - 9:50 pm
MDW
-
BOS
2h 15mnonstop
$140Southwest
Sat, Feb 28 - Mon, Mar 2
Multiple Airlines Logo
5:50 pm - 1:56 pm
BOS
-
MDW
21h 06m
1 stop
Multiple Airlines Logo
5:16 pm - 1:13 am
MDW
-
BOS
6h 57m
1 stop
$145Multiple Airlines
Wed, Feb 25 - Thu, Feb 26
Frontier Logo
6:00 am - 4:16 pm
BOS
-
MDW
11h 16m
1 stop
Frontier Logo
2:19 pm - 1:13 am
MDW
-
BOS
9h 54m
1 stop
$148Frontier
Thu, Feb 26 - Mon, Mar 2
Multiple Airlines Logo
1:12 pm - 7:47 pm
BDL
-
MDW
7h 35m
1 stop
Multiple Airlines Logo
9:51 pm - 6:11 pm
MDW
-
BDL
19h 20m
2 stops
$290Multiple Airlines
Thu, Mar 12 - Mon, Mar 16
Frontier Logo
1:07 pm - 10:19 pm
BDL
-
MDW
10h 12m
1 stop
Frontier Logo
6:48 pm - 12:12 pm
MDW
-
BDL
16h 24m
2 stops
$298Frontier
Sun, Mar 22 - Wed, Mar 25
Delta Logo
6:00 am - 8:43 am
ALB
-
MDW
3h 43m
1 stop
Delta Logo
5:14 pm - 11:58 pm
MDW
-
ALB
5h 44m
1 stop
$299Delta
Thu, May 7 - Tue, May 12

Southwest flights from Massachusetts to Chicago Midway Airport

Our best Southwest deals on Massachusetts to Chicago Midway Airport flight tickets
Southwest
May 1
BOS3:45 pmBoston Logan Intl
2h 45m
MDW5:30 pmChicago Midway
May 4
MDW7:00 pmChicago Midway
2h 20m
BOS10:20 pmBoston Logan Intl
$132
Southwest
Mar 4
BOS5:30 amBoston Logan Intl
2h 50m
MDW7:20 amChicago Midway
Mar 7
MDW7:40 amChicago Midway
2h 15m
BOS10:55 amBoston Logan Intl
$133
Southwest
Feb 28
BOS2:10 pmBoston Logan Intl
6h 15m
1 stop
MDW7:25 pmChicago Midway
Mar 2
MDW6:35 pmChicago Midway
2h 15m
BOS9:50 pmBoston Logan Intl
$134

Delta flights from Massachusetts to Chicago Midway Airport

Our best Delta deals on Massachusetts to Chicago Midway Airport flight tickets
Delta
May 7
ALB6:00 amAlbany Intl
3h 43m
1 stop
MDW8:43 amChicago Midway
May 12
MDW5:14 pmChicago Midway
5h 44m
1 stop
ALB11:58 pmAlbany Intl
$299
Delta
Feb 25
BDL6:05 amHartford Bradley Intl
8h 00m
1 stop
MDW1:05 pmChicago Midway
Feb 25
MDW6:20 pmChicago Midway
4h 19m
1 stop
BDL11:39 pmHartford Bradley Intl
$309
Delta
Apr 19
ALB6:00 pmAlbany Intl
5h 28m
1 stop
MDW10:28 pmChicago Midway
Apr 22
MDW6:00 amChicago Midway
5h 13m
1 stop
ALB12:13 pmAlbany Intl
$319

momondo Fare Finder

 
Customize your flight search to find flights from Massachusetts to Chicago Midway Airport 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 7, 2026.
Use the filters below to find and compare flights from Massachusetts to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 5/1

3:45 pm-5:30 pm

Nonstop2h 45m

Chicago Midway

Mon 5/4

7:00 pm-10:20 pm

Nonstop2h 20m

$132

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 3/4

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Sat 3/7

7:40 am-10:55 am

Nonstop2h 15m

$133

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 2/28

2:10 pm-7:25 pm

1 stop6h 15m

Chicago Midway

Mon 3/2

6:35 pm-9:50 pm

Nonstop2h 15m

$134

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 3/9

6:25 pm-8:25 pm

Nonstop3h 00m

Chicago Midway

Thu 3/12

3:30 pm-6:45 pm

Nonstop2h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 2/28

9:00 am-4:20 pm

2 stops8h 20m

Chicago Midway

Mon 3/2

6:35 pm-9:50 pm

Nonstop2h 15m

$140

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 2/25

5:50 pm-1:56 pm

1 stop21h 06m

Chicago Midway

Thu 2/26

5:16 pm-1:13 am

1 stop6h 57m

$145

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 2/26

6:00 am-4:16 pm

1 stop11h 16m

Chicago Midway

Mon 3/2

2:19 pm-1:13 am

1 stop9h 54m

$148

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 3/12

1:12 pm-7:47 pm

1 stop7h 35m

Chicago Midway

Mon 3/16

9:51 pm-6:11 pm

2 stops19h 20m

$290

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sun 3/22

1:07 pm-10:19 pm

1 stop10h 12m

Chicago Midway

Wed 3/25

6:48 pm-12:12 pm

2 stops16h 24m

$298

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Thu 5/7

6:00 am-8:43 am

1 stop3h 43m

Chicago Midway

Tue 5/12

5:14 pm-11:58 pm

1 stop5h 44m

$299

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 Midway Airport

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 Midway Airport?

The month of December is, on average, the cheapest month to fly to Chicago Midway Airport from Massachusetts, with most prices found around $137. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Massachusetts during the month January is also very affordable. Most momondo users find prices during this month for around $183.

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

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Massachusetts. The lowest ticket price found for a Wednesday departure recently was $282. 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, Sunday is the most expensive day to depart from Massachusetts because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $401.

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

Flying to Chicago Midway Airport from Massachusetts in the evening is the least expensive time of day to depart. momondo users have found prices as low as $266 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $350. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Massachusetts to Chicago Midway flight route?

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

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

You are more likely to see cheaper flights to Chicago Midway Airport from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $256 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Massachusetts for as low as $161 on momondo.

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

There is only 1 cabin class available to choose from on Massachusetts to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap Massachusetts to Chicago Midway Airport flight deals and tips

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

Best Price Found

$155

Fastest flight time

2h 10m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Massachusetts in the past 72 hours is $155. The best round-trip flight deal from Massachusetts to Chicago Midway Airport found on momondo in the last 72 hours is $273.
The fastest flight from Massachusetts to Chicago Midway Airport takes 2h 10m
Direct flights go from Massachusetts to Chicago Midway Airport every day.
Search flight deals

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

    Prices for flights from Massachusetts to Chicago Midway Airport are refreshed on a daily basis.

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

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

    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 Massachusetts to Chicago Midway Airport.

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

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

Best airlines flying from Massachusetts to Chicago Midway Airport

Compare and see reviews for airlines that fly from Massachusetts to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $117Free CancellationRating
8.0
4,280 reviews
Search Southwest flights
DeltaPriceFrom $207Free CancellationRating
7.9
8,172 reviews
Search Delta 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?

Yes. All flights to Chicago from Massachusetts on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo helps you find the best flight between Massachusetts and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Price alerts on flights to Chicago from Massachusetts 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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