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Cheap flights from Massachusetts to Chicago from $99

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 9/16. 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 Massachusetts to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:35 am - 7:10 am
BOS
-
MDW
2h 35mnonstop
Southwest Logo
4:00 pm - 7:20 pm
MDW
-
BOS
2h 20mnonstop
$178Southwest
Wed, Jul 8 - Mon, Jul 13
Southwest Logo
5:35 am - 7:10 am
BOS
-
MDW
2h 35mnonstop
Southwest Logo
7:35 pm - 10:55 pm
MDW
-
BOS
2h 20mnonstop
$179Southwest
Tue, Jul 14 - Fri, Jul 17
Southwest Logo
8:45 am - 2:55 pm
BOS
-
MDW
7h 10m
1 stop
Southwest Logo
5:25 am - 8:40 am
MDW
-
BOS
2h 15mnonstop
$180Southwest
Sat, Jul 4 - Sat, Jul 11
Southwest Logo
5:35 am - 7:10 am
BOS
-
MDW
2h 35mnonstop
Southwest Logo
6:00 pm - 9:20 pm
MDW
-
BOS
2h 20mnonstop
$182Southwest
Tue, Jul 28 - Wed, Aug 5
Southwest Logo
5:20 am - 6:55 am
BOS
-
MDW
2h 35mnonstop
Southwest Logo
5:15 am - 8:25 am
MDW
-
BOS
2h 10mnonstop
$183Southwest
Sat, Jul 18 - Sun, Jul 19
Southwest Logo
8:45 am - 5:10 pm
BOS
-
MDW
9h 25m
2 stops
Southwest Logo
5:25 am - 8:40 am
MDW
-
BOS
2h 15mnonstop
$185Southwest
Sat, Jul 4 - Sat, Jul 11
Southwest Logo
5:25 am - 7:00 am
BOS
-
MDW
2h 35mnonstop
Southwest Logo
4:00 pm - 7:20 pm
MDW
-
BOS
2h 20mnonstop
$187Southwest
Thu, Jul 9 - Mon, Jul 13
Southwest Logo
5:35 am - 7:10 am
BOS
-
MDW
2h 35mnonstop
Southwest Logo
2:45 pm - 11:30 pm
MDW
-
BOS
7h 45m
1 stop
$189Southwest
Tue, Jul 14 - Fri, Jul 17
Delta Logo
5:30 am - 9:17 am
BDL
-
MDW
4h 47m
1 stop
Delta Logo
6:42 pm - 11:51 pm
MDW
-
BDL
4h 09m
1 stop
$358Delta
Tue, Aug 11 - Thu, Aug 13
Delta Logo
4:30 pm - 10:15 pm
BDL
-
MDW
6h 45m
1 stop
Delta Logo
5:10 pm - 11:54 pm
MDW
-
BDL
5h 44m
1 stop
$359Delta
Sat, Jul 18 - Tue, Jul 21

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Southwest flights from Massachusetts to Chicago Midway Airport

Our best Southwest deals on Massachusetts to Chicago Midway Airport flight tickets
Southwest
Aug 22
BOS7:05 amBoston Logan Intl
2h 35m
MDW8:40 amChicago Midway
Aug 29
MDW9:05 amChicago Midway
2h 20m
BOS12:25 pmBoston Logan Intl
$175
Southwest
Jul 8
BOS5:35 amBoston Logan Intl
2h 35m
MDW7:10 amChicago Midway
Jul 13
MDW4:00 pmChicago Midway
2h 20m
BOS7:20 pmBoston Logan Intl
$178
Southwest
Jul 14
BOS5:35 amBoston Logan Intl
2h 35m
MDW7:10 amChicago Midway
Jul 17
MDW7:35 pmChicago Midway
2h 20m
BOS10:55 pmBoston Logan Intl
$179

Delta flights from Massachusetts to Chicago Midway Airport

Our best Delta deals on Massachusetts to Chicago Midway Airport flight tickets
Delta
Oct 20
ALB1:59 pmAlbany Intl
19h 50m
2 stops
MDW8:49 amChicago Midway
Oct 27
MDW6:30 pmChicago Midway
3h 40m
1 stop
ALB11:10 pmAlbany Intl
$351
Delta
Oct 14
BDL1:00 pmHartford Bradley Intl
6h 37m
1 stop
MDW6:37 pmChicago Midway
Oct 19
MDW5:25 pmChicago Midway
5h 20m
1 stop
BDL11:45 pmHartford Bradley Intl
$358
Delta
Jul 18
BDL4:30 pmHartford Bradley Intl
6h 45m
1 stop
MDW10:15 pmChicago Midway
Jul 21
MDW5:10 pmChicago Midway
5h 44m
1 stop
BDL11:54 pmHartford Bradley Intl
$359

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 June 23, 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

Cheapest round-trip

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 7/8

5:35 am-7:10 am

Nonstop2h 35m

Chicago Midway

Mon 7/13

4:00 pm-7:20 pm

Nonstop2h 20m

$178

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 7/14

5:35 am-7:10 am

Nonstop2h 35m

Chicago Midway

Fri 7/17

7:35 pm-10:55 pm

Nonstop2h 20m

$179

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 7/4

8:45 am-2:55 pm

1 stop7h 10m

Chicago Midway

Sat 7/11

5:25 am-8:40 am

Nonstop2h 15m

$180

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 7/28

5:35 am-7:10 am

Nonstop2h 35m

Chicago Midway

Wed 8/5

6:00 pm-9:20 pm

Nonstop2h 20m

$182
Quickest round-trip

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 7/18

5:20 am-6:55 am

Nonstop2h 35m

Chicago Midway

Sun 7/19

5:15 am-8:25 am

Nonstop2h 10m

$183

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 7/4

8:45 am-5:10 pm

2 stops9h 25m

Chicago Midway

Sat 7/11

5:25 am-8:40 am

Nonstop2h 15m

$185

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 7/9

5:25 am-7:00 am

Nonstop2h 35m

Chicago Midway

Mon 7/13

4:00 pm-7:20 pm

Nonstop2h 20m

$187

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 7/14

5:35 am-7:10 am

Nonstop2h 35m

Chicago Midway

Fri 7/17

2:45 pm-11:30 pm

1 stop7h 45m

$189

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 8/11

5:30 am-9:17 am

1 stop4h 47m

Chicago Midway

Thu 8/13

6:42 pm-11:51 pm

1 stop4h 09m

$358

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 7/18

4:30 pm-10:15 pm

1 stop6h 45m

Chicago Midway

Tue 7/21

5:10 pm-11:54 pm

1 stop5h 44m

$359

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 October is, on average, the cheapest month to fly to Chicago Midway Airport from Massachusetts, with most prices found around $67. If you are unable to visit Chicago Midway Airport during the month of October, then departing from Massachusetts during the month November is also very affordable. Most momondo users find prices during this month for around $88.

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

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Massachusetts. The lowest ticket price found for a Thursday departure recently was $340. 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 $445.

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 $280 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $381. 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 from Massachusetts 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 $269 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 $130 on momondo.

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

There is only 1 cabin class available to choose from on Massachusetts to Chicago Midway Airport 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

$187

Fastest flight time

2h 05m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Massachusetts in the past 72 hours is $187. The best round-trip flight deal from Massachusetts to Chicago Midway Airport found on momondo in the last 72 hours is $267.
The fastest flight from Massachusetts to Chicago Midway Airport takes 2h 05m
Direct flights go from Massachusetts to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Massachusetts to Chicago Midway Airport

  • 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
DeltaPriceFrom $88Free CancellationRating
7.8
8,424 reviews
Search Delta flights
JetBluePriceFrom $117Free CancellationRating
7.1
2,998 reviews
Search JetBlue flights
SouthwestPriceFrom $131Free CancellationRating
7.9
4,241 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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New Buffalo
Hammond
Benton Harbor
Portage
Saint Joseph
Lansing
Valparaiso
Schererville
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.

An easier way to manage your Chicago Midway Airport trip

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