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Cheap flights from Massachusetts to Chicago from $61

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 12/11. 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

Enter your travel dates to find the best prices.
Southwest Logo
5:45 am - 1:00 pmBOS-MDW
8h 15m2 stops
Southwest Logo
6:15 pm - 9:35 pmMDW-BOS
2h 20mnonstop
$122Southwest
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Tue, Nov 11 - Wed, Nov 12
Frontier Logo
11:28 am - 6:08 pmBOS-MDW
7h 40m1 stop
Frontier Logo
6:00 am - 12:58 amMDW-BOS
17h 58m1 stop
$124Frontier
Find Deal
Thu, Dec 11 - Sun, Jan 18
Frontier Logo
11:28 am - 10:12 pmBOS-MDW
11h 44m1 stop
Frontier Logo
7:27 pm - 10:22 amMDW-BOS
13h 55m1 stop
$125Frontier
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Thu, Dec 4 - Sun, Dec 7
Southwest Logo
5:15 am - 7:00 amBOS-MDW
2h 45mnonstop
Southwest Logo
9:35 am - 12:50 pmMDW-BOS
2h 15mnonstop
$127Southwest
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Sun, Nov 9 - Thu, Nov 13
Frontier Logo
11:28 am - 6:08 pmBOS-MDW
7h 40m1 stop
Frontier Logo
6:15 am - 10:22 amMDW-BOS
27h 07m1 stop
$128Frontier
Find Deal
Thu, Dec 11 - Sun, Dec 14
Southwest Logo
9:05 am - 2:05 pmBOS-MDW
6h 00m2 stops
Southwest Logo
11:25 am - 5:20 pmMDW-BOS
4h 55m1 stop
$132Southwest
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Tue, Nov 11 - Wed, Nov 12
Frontier Logo
11:19 am - 10:12 pmBOS-MDW
11h 53m1 stop
Frontier Logo
7:27 pm - 10:22 amMDW-BOS
13h 55m1 stop
$133Frontier
Find Deal
Fri, Dec 5 - Sun, Dec 7
Frontier Logo
11:28 am - 6:08 pmBOS-MDW
7h 40m1 stop
Frontier Logo
8:15 am - 10:08 amMDW-BOS
24h 53m1 stop
$134Frontier
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Thu, Dec 11 - Wed, Dec 31
Delta Logo
1:01 pm - 6:00 pmBDL-MDW
5h 59m1 stop
Delta Logo
5:29 pm - 11:47 pmMDW-BDL
5h 18m1 stop
$235Delta
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Wed, Dec 3 - Tue, Dec 9
Delta Logo
6:58 pm - 11:40 pmALB-MDW
5h 42m1 stop
Delta Logo
10:49 am - 5:51 pmMDW-ALB
6h 02m1 stop
$244Delta
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Mon, Nov 24 - Wed, Dec 3

Frontier flights from Massachusetts to Chicago Midway Airport

Our best Frontier deals on Massachusetts to Chicago Midway Airport flight tickets
Frontier
Dec 11
BOS11:28 amBoston Logan Intl
7h 40m
1 stop
MDW6:08 pmChicago Midway
Jan 18
MDW6:00 amChicago Midway
17h 58m
1 stop
BOS12:58 amBoston Logan Intl
$124
Find similar
Frontier
Dec 4
BOS11:28 amBoston Logan Intl
11h 44m
1 stop
MDW10:12 pmChicago Midway
Dec 7
MDW7:27 pmChicago Midway
13h 55m
1 stop
BOS10:22 amBoston Logan Intl
$125
Find similar
Frontier
Dec 11
BOS11:28 amBoston Logan Intl
7h 40m
1 stop
MDW6:08 pmChicago Midway
Dec 14
MDW6:15 amChicago Midway
27h 07m
1 stop
BOS10:22 amBoston Logan Intl
$128
Find similar

Delta flights from Massachusetts to Chicago Midway Airport

Our best Delta deals on Massachusetts to Chicago Midway Airport flight tickets
Delta
Dec 3
BDL1:01 pmHartford Bradley Intl
5h 59m
1 stop
MDW6:00 pmChicago Midway
Dec 9
MDW5:29 pmChicago Midway
5h 18m
1 stop
BDL11:47 pmHartford Bradley Intl
$235
Find similar
Delta
Nov 24
ALB6:58 pmAlbany Intl
5h 42m
1 stop
MDW11:40 pmChicago Midway
Dec 3
MDW10:49 amChicago Midway
6h 02m
1 stop
ALB5:51 pmAlbany Intl
$244
Find similar
Delta
Dec 2
BDL5:23 amHartford Bradley Intl
4h 31m
1 stop
MDW8:54 amChicago Midway
Dec 9
MDW5:29 pmChicago Midway
5h 18m
1 stop
BDL11:47 pmHartford Bradley Intl
$245
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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 October 27, 2025.
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

Tue 11/11

5:45 am-1:00 pm

2 stops8h 15m

Chicago Midway

Wed 11/12

6:15 pm-9:35 pm

Nonstop2h 20m

$122

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 12/11

11:28 am-6:08 pm

1 stop7h 40m

Chicago Midway

Sun 1/18

6:00 am-12:58 am

1 stop17h 58m

$124

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 12/4

11:28 am-10:12 pm

1 stop11h 44m

Chicago Midway

Sun 12/7

7:27 pm-10:22 am

1 stop13h 55m

$125

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sun 11/9

5:15 am-7:00 am

Nonstop2h 45m

Chicago Midway

Thu 11/13

9:35 am-12:50 pm

Nonstop2h 15m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 12/11

11:28 am-6:08 pm

1 stop7h 40m

Chicago Midway

Sun 12/14

6:15 am-10:22 am

1 stop27h 07m

$128

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 11/11

9:05 am-2:05 pm

2 stops6h 00m

Chicago Midway

Wed 11/12

11:25 am-5:20 pm

1 stop4h 55m

$132

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 12/5

11:19 am-10:12 pm

1 stop11h 53m

Chicago Midway

Sun 12/7

7:27 pm-10:22 am

1 stop13h 55m

$133

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 12/11

11:28 am-6:08 pm

1 stop7h 40m

Chicago Midway

Wed 12/31

8:15 am-10:08 am

1 stop24h 53m

$134

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 12/3

1:01 pm-6:00 pm

1 stop5h 59m

Chicago Midway

Tue 12/9

5:29 pm-11:47 pm

1 stop5h 18m

$235

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Mon 11/24

6:58 pm-11:40 pm

1 stop5h 42m

Chicago Midway

Wed 12/3

10:49 am-5:51 pm

1 stop6h 02m

$244

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 January is, on average, the cheapest month to fly to Chicago Midway Airport from Massachusetts, with most prices found around $188. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Massachusetts during the month September is also very affordable. Most momondo users find prices during this month for around $213.

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 $292. 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 $438.

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

Flying to Chicago Midway Airport from Massachusetts at noon is the least expensive time of day to depart. momondo users have found prices as low as $311 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $347. 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 $263 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 $164 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

$198

Fastest flight time

2h 15m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Massachusetts in the past 72 hours is $198. The best round-trip flight deal from Massachusetts to Chicago Midway Airport found on momondo in the last 72 hours is $246.
The fastest flight from Massachusetts to Chicago Midway Airport takes 2h 15m
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
4,236 reviews
Search Southwest flights
DeltaPriceFrom $227Free CancellationRating
7.9
7,996 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
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
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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