Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Massachusetts to Chicago from $115

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.
Frontier Logo
9:35 am - 4:26 pmBOS  Boston Logan Intl-MDW Chicago Midway
7h 51m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:47 pm - 9:29 amMDW  Chicago Midway-BOS Boston Logan Intl
11h 42m1 stop Orlando
$217Frontier
Sat, Jan 9 - Mon, Jan 18
Frontier Logo
9:35 am - 4:26 pmBOS  Boston Logan Intl-MDW Chicago Midway
7h 51m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:47 pm - 9:29 amMDW  Chicago Midway-BOS Boston Logan Intl
11h 42m1 stop Orlando
$217Frontier
Sat, Jan 9 - Fri, Jan 15
Frontier Logo
9:35 am - 4:26 pmBOS  Boston Logan Intl-MDW Chicago Midway
7h 51m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:30 pm - 9:06 amMDW  Chicago Midway-BOS Boston Logan Intl
11h 36m1 stop Orlando
$217Frontier
Wed, Jan 6 - Thu, Jan 7
Southwest Logo
7:25 am - 9:15 amBOS  Boston Logan Intl-MDW Chicago Midway
2h 50mnonstop
Southwest Logo
8:20 am - 11:45 amMDW  Chicago Midway-BOS Boston Logan Intl
2h 25mnonstop
$247Southwest
Thu, Jan 14 - Tue, Jan 19
Southwest Logo
7:10 am - 8:55 amBOS  Boston Logan Intl-MDW Chicago Midway
2h 45mnonstop
Southwest Logo
6:25 pm - 9:45 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 20mnonstop
$247Southwest
Tue, Dec 1 - Thu, Dec 3
Southwest Logo
7:10 am - 8:55 amBOS  Boston Logan Intl-MDW Chicago Midway
2h 45mnonstop
Southwest Logo
8:30 am - 12:00 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 30mnonstop
$247Southwest
Thu, Dec 10 - Mon, Dec 14
Delta Logo
10:10 am - 4:16 pmBOS  Boston Logan Intl-MDW Chicago Midway
7h 06m1 stop Atlanta Hartsfield-Jackson
Delta Logo
10:24 am - 6:58 pmMDW  Chicago Midway-BOS Boston Logan Intl
7h 34m1 stop Minneapolis St Paul
$325Delta
Thu, Dec 10 - Mon, Dec 14
Delta Logo
5:27 am - 9:37 amBOS  Boston Logan Intl-MDW Chicago Midway
5h 10m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:41 pm - 11:58 pmMDW  Chicago Midway-BOS Boston Logan Intl
4h 17m1 stop Detroit Metropolitan Wayne County
$325Delta
Thu, Dec 10 - Sat, Dec 12
Delta Logo
5:30 am - 11:25 amBOS  Boston Logan Intl-MDW Chicago Midway
6h 55m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:37 am - 3:54 pmMDW  Chicago Midway-BOS Boston Logan Intl
5h 17m1 stop Detroit Metropolitan Wayne County
$326Delta
Thu, Nov 26 - Tue, Dec 1
JetBlue Logo
7:35 am - 9:20 amBOS  Boston Logan Intl-MDW Chicago Midway
2h 45mnonstop
JetBlue Logo
1:40 pm - 4:50 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 10mnonstop
$487JetBlue
Fri, Mar 12 - Sun, Mar 14

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Frontier flights from Massachusetts to Chicago Midway Airport

Our best Frontier deals on Massachusetts to Chicago Midway Airport flight tickets
Frontier
Jan 9
BOS9:35 amBoston Logan Intl
7h 51m
1 stop
MDW4:26 pmChicago Midway
Jan 18
MDW8:47 pmChicago Midway
11h 42m
1 stop
BOS9:29 amBoston Logan Intl
$217
Frontier
Nov 17
BOS12:15 pmBoston Logan Intl
6h 32m
1 stop
MDW5:47 pmChicago Midway
Nov 24
MDW8:42 pmChicago Midway
12h 29m
1 stop
BOS10:11 amBoston Logan Intl
$218
Frontier
Nov 19
BOS12:39 pmBoston Logan Intl
12h 08m
1 stop
MDW11:47 pmChicago Midway
Nov 25
MDW8:42 pmChicago Midway
12h 29m
1 stop
BOS10:11 amBoston Logan Intl
$226

Southwest flights from Massachusetts to Chicago Midway Airport

Our best Southwest deals on Massachusetts to Chicago Midway Airport flight tickets
Southwest
Dec 1
BOS7:10 amBoston Logan Intl
2h 45m
MDW8:55 amChicago Midway
Dec 3
MDW1:20 pmChicago Midway
7h 35m
2 stops
BOS9:55 pmBoston Logan Intl
$262
Southwest
Dec 1
BOS5:20 amBoston Logan Intl
7h 45m
1 stop
MDW12:05 pmChicago Midway
Dec 1
MDW3:50 pmChicago Midway
4h 55m
1 stop
BOS9:45 pmBoston Logan Intl
$267
Southwest
Dec 1
BOS5:35 pmBoston Logan Intl
4h 55m
1 stop
MDW9:30 pmChicago Midway
Dec 3
MDW1:20 pmChicago Midway
7h 35m
2 stops
BOS9:55 pmBoston Logan Intl
$272

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

Sat 1/9

9:35 am-4:26 pm

1 stop7h 51m

Chicago Midway

Mon 1/18

8:47 pm-9:29 am

1 stop11h 42m

$217

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Sat 1/9

9:35 am-4:26 pm

1 stop7h 51m

Chicago Midway

Fri 1/15

8:47 pm-9:29 am

1 stop11h 42m

$217

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Wed 1/6

9:35 am-4:26 pm

1 stop7h 51m

Chicago Midway

Thu 1/7

8:30 pm-9:06 am

1 stop11h 36m

$217

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Thu 1/14

7:25 am-9:15 am

Nonstop2h 50m

Chicago Midway

Tue 1/19

8:20 am-11:45 am

Nonstop2h 25m

$247

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Tue 12/1

7:10 am-8:55 am

Nonstop2h 45m

Chicago Midway

Thu 12/3

6:25 pm-9:45 pm

Nonstop2h 20m

$247

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Thu 12/10

7:10 am-8:55 am

Nonstop2h 45m

Chicago Midway

Mon 12/14

8:30 am-12:00 pm

Nonstop2h 30m

$247

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Thu 12/10

10:10 am-4:16 pm

1 stop7h 06m

Chicago Midway

Mon 12/14

10:24 am-6:58 pm

1 stop7h 34m

$325

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Thu 12/10

5:27 am-9:37 am

1 stop5h 10m

Chicago Midway

Sat 12/12

6:41 pm-11:58 pm

1 stop4h 17m

$325

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Thu 11/26

5:30 am-11:25 am

1 stop6h 55m

Chicago Midway

Tue 12/1

9:37 am-3:54 pm

1 stop5h 17m

$326
Quickest round-trip

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Fri 3/12

7:35 am-9:20 am

Nonstop2h 45m

Chicago Midway

Sun 3/14

1:40 pm-4:50 pm

Nonstop2h 10m

$487

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $134. 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 $167.

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 $359. 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 $461.

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 $352 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $401. 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 $282 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.

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

$115

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 $115. The best round-trip flight deal from Massachusetts to Chicago Midway Airport found on momondo in the last 72 hours is $217.
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

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
8,698 reviews
Search Delta flights
JetBluePriceFrom $150Free CancellationRating
7.1
3,065 reviews
Search JetBlue flights
SouthwestPriceFrom $157Free CancellationRating
8.0
4,215 reviews
Search Southwest flights
American AirlinesPriceFrom $181Free CancellationRating
7.0
12,233 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
Lansing
Saint Joseph
Benton Harbor
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.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 12/3
Thu 12/10
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago