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Cheap flights from Massachusetts to Chicago from $118

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
3:50 pm - 7:25 pmBOS  Boston Logan Intl-MDW Chicago Midway
4h 35m1 stop Baltimore/Washington
Southwest Logo
7:55 am - 4:05 pmMDW  Chicago Midway-BOS Boston Logan Intl
7h 10m2 stops Buffalo Baltimore/Washington
$214Southwest
Tue, Oct 27 - Wed, Oct 28
Southwest Logo
11:45 am - 5:10 pmBOS  Boston Logan Intl-MDW Chicago Midway
6h 25m1 stop Lambert-St Louis
Southwest Logo
7:55 am - 4:05 pmMDW  Chicago Midway-BOS Boston Logan Intl
7h 10m2 stops Buffalo Baltimore/Washington
$214Southwest
Tue, Oct 27 - Wed, Oct 28
Southwest Logo
6:45 am - 4:05 pmBOS  Boston Logan Intl-MDW Chicago Midway
10h 20m1 stop Baltimore/Washington
Southwest Logo
9:40 am - 4:50 pmMDW  Chicago Midway-BOS Boston Logan Intl
6h 10m1 stop Lambert-St Louis
$214Southwest
Tue, Oct 20 - Tue, Nov 3
Southwest Logo
6:45 am - 4:05 pmBOS  Boston Logan Intl-MDW Chicago Midway
10h 20m1 stop Baltimore/Washington
Southwest Logo
8:10 am - 4:05 pmMDW  Chicago Midway-BOS Boston Logan Intl
6h 55m1 stop Baltimore/Washington
$214Southwest
Tue, Oct 20 - Tue, Oct 27
Frontier Logo
12:15 pm - 11:47 pmBOS  Boston Logan Intl-MDW Chicago Midway
12h 32m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:42 pm - 10:11 amMDW  Chicago Midway-BOS Boston Logan Intl
12h 29m1 stop Orlando
$246Frontier
Tue, Nov 17 - Sun, Nov 22
Frontier Logo
12:39 pm - 11:47 pmBOS  Boston Logan Intl-MDW Chicago Midway
12h 08m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:42 pm - 7:41 amMDW  Chicago Midway-BOS Boston Logan Intl
11h 59m1 stop Atlanta Hartsfield-Jackson
$246Frontier
Wed, Nov 18 - Thu, Nov 19
Frontier Logo
12:15 pm - 5:47 pmBOS  Boston Logan Intl-MDW Chicago Midway
6h 32m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:42 pm - 10:11 amMDW  Chicago Midway-BOS Boston Logan Intl
12h 29m1 stop Orlando
$246Frontier
Tue, Nov 17 - Sat, Nov 21
Delta Logo
1:05 pm - 6:00 pmBOS  Boston Logan Intl-MDW Chicago Midway
5h 55m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:44 pm - 11:59 pmMDW  Chicago Midway-BOS Boston Logan Intl
4h 15m1 stop Detroit Metropolitan Wayne County
$291Delta
Wed, Nov 4 - Sat, Nov 7
Delta Logo
9:15 am - 12:47 pmBOS  Boston Logan Intl-MDW Chicago Midway
4h 32m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:44 pm - 11:59 pmMDW  Chicago Midway-BOS Boston Logan Intl
4h 15m1 stop Detroit Metropolitan Wayne County
$314Delta
Thu, Oct 15 - Mon, Oct 19
Delta Logo
5:35 am - 9:32 amBOS  Boston Logan Intl-MDW Chicago Midway
4h 57m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:44 pm - 11:59 pmMDW  Chicago Midway-BOS Boston Logan Intl
4h 15m1 stop Detroit Metropolitan Wayne County
$315Delta
Tue, Oct 6 - Sat, Oct 10

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Frontier flights from Massachusetts to Chicago Midway Airport

Our best Frontier deals on Massachusetts to Chicago Midway Airport flight tickets
Frontier
Nov 17
BOS12:15 pmBoston Logan Intl
6h 32m
1 stop
MDW5:47 pmChicago Midway
Nov 20
MDW8:42 pmChicago Midway
12h 29m
1 stop
BOS10:11 amBoston Logan Intl
$248
Frontier
Nov 17
BOS12:15 pmBoston Logan Intl
12h 32m
1 stop
MDW11:47 pmChicago Midway
Nov 19
MDW6:42 pmChicago Midway
11h 59m
1 stop
BOS7:41 amBoston Logan Intl
$250

Southwest flights from Massachusetts to Chicago Midway Airport

Our best Southwest deals on Massachusetts to Chicago Midway Airport flight tickets
Southwest
Nov 10
BOS5:20 amBoston Logan Intl
7h 45m
1 stop
MDW12:05 pmChicago Midway
Nov 11
MDW7:35 amChicago Midway
8h 35m
2 stops
BOS5:10 pmBoston Logan Intl
$214
Southwest
Oct 15
BOS10:00 pmBoston Logan Intl
2h 40m
MDW11:40 pmChicago Midway
Oct 19
MDW7:50 amChicago Midway
2h 20m
BOS11:10 amBoston Logan Intl
$215
Southwest
Oct 3
BOS7:40 amBoston Logan Intl
2h 35m
MDW9:15 amChicago Midway
Oct 7
MDW7:55 amChicago Midway
6h 00m
2 stops
BOS2:55 pmBoston Logan Intl
$217

momondo Fare Finder

 
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 Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Tue 10/27

3:50 pm-7:25 pm

1 stop4h 35m

Chicago Midway

Wed 10/28

7:55 am-4:05 pm

2 stops7h 10m

$214

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Tue 10/27

11:45 am-5:10 pm

1 stop6h 25m

Chicago Midway

Wed 10/28

7:55 am-4:05 pm

2 stops7h 10m

$214

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Tue 10/20

6:45 am-4:05 pm

1 stop10h 20m

Chicago Midway

Tue 11/3

9:40 am-4:50 pm

1 stop6h 10m

$214

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Tue 10/20

6:45 am-4:05 pm

1 stop10h 20m

Chicago Midway

Tue 10/27

8:10 am-4:05 pm

1 stop6h 55m

$214

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Tue 11/17

12:15 pm-11:47 pm

1 stop12h 32m

Chicago Midway

Sun 11/22

8:42 pm-10:11 am

1 stop12h 29m

$246

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Wed 11/18

12:39 pm-11:47 pm

1 stop12h 08m

Chicago Midway

Thu 11/19

6:42 pm-7:41 am

1 stop11h 59m

$246

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Tue 11/17

12:15 pm-5:47 pm

1 stop6h 32m

Chicago Midway

Sat 11/21

8:42 pm-10:11 am

1 stop12h 29m

$246

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Wed 11/4

1:05 pm-6:00 pm

1 stop5h 55m

Chicago Midway

Sat 11/7

6:44 pm-11:59 pm

1 stop4h 15m

$291
Quickest round-trip

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Thu 10/15

9:15 am-12:47 pm

1 stop4h 32m

Chicago Midway

Mon 10/19

6:44 pm-11:59 pm

1 stop4h 15m

$314

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Tue 10/6

5:35 am-9:32 am

1 stop4h 57m

Chicago Midway

Sat 10/10

6:44 pm-11:59 pm

1 stop4h 15m

$315

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 $162. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Massachusetts during the month December is also very affordable. Most momondo users find prices during this month for around $177.

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 $355. 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 $465.

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 $333 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $399. 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 $289 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 $238 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.

Can stopping save me money on Massachusetts to Chicago Midway Airport flights?

You could potentially save up to 1% on your flight if you consider stops on a Massachusetts to Chicago Midway Airport flight.

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

$118

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 $118. The best round-trip flight deal from Massachusetts to Chicago Midway Airport found on momondo in the last 72 hours is $214.
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

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
8,595 reviews
Search Delta flights
JetBluePriceFrom $117Free CancellationRating
7.1
3,037 reviews
Search JetBlue flights
SouthwestPriceFrom $144Free CancellationRating
8.0
4,196 reviews
Search Southwest flights
American AirlinesPriceFrom $181Free CancellationRating
7.0
12,080 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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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