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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 11/4. 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
10:55 am - 12:30 pmBOS  Boston Logan Intl-MDW Chicago Midway
2h 35mnonstop
Southwest Logo
1:15 pm - 4:20 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 05mnonstop
$207Southwest
Wed, Oct 28 - Tue, Nov 3
Southwest Logo
10:05 am - 11:35 amBOS  Boston Logan Intl-MDW Chicago Midway
2h 30mnonstop
Southwest Logo
6:00 pm - 9:25 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 25mnonstop
$207Southwest
Tue, Sep 15 - Tue, Sep 15
Southwest Logo
8:40 am - 10:15 amBOS  Boston Logan Intl-MDW Chicago Midway
2h 35mnonstop
Southwest Logo
6:00 pm - 9:25 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 25mnonstop
$207Southwest
Sat, Sep 12 - Tue, Sep 15
Southwest Logo
10:55 am - 12:30 pmBOS  Boston Logan Intl-MDW Chicago Midway
2h 35mnonstop
Southwest Logo
4:05 pm - 7:25 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 20mnonstop
$207Southwest
Tue, Oct 27 - Sat, Oct 31
Multiple Airlines Logo
12:35 pm - 9:53 pmBOS  Boston Logan Intl-MDW Chicago Midway
10h 18m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
1:26 pm - 10:42 amMDW  Chicago Midway-BOS Boston Logan Intl
20h 16m1 stop Knoxville McGhee Tyson
$213Multiple Airlines
Wed, Oct 28 - Mon, Nov 2
Multiple Airlines Logo
11:28 am - 9:58 pmBOS  Boston Logan Intl-MDW Chicago Midway
11h 30m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
1:26 pm - 10:42 amMDW  Chicago Midway-BOS Boston Logan Intl
20h 16m1 stop Knoxville McGhee Tyson
$232Multiple Airlines
Wed, Oct 21 - Mon, Oct 26
Multiple Airlines Logo
11:28 am - 9:58 pmBOS  Boston Logan Intl-MDW Chicago Midway
11h 30m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
2:26 pm - 8:12 amMDW  Chicago Midway-BOS Boston Logan Intl
16h 46m1 stop Knoxville McGhee Tyson
$251Multiple Airlines
Wed, Oct 21 - Fri, Oct 23
Delta Logo
6:00 am - 9:17 amALB  Albany Intl-MDW Chicago Midway
4h 17m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:05 am - 1:26 pmMDW  Chicago Midway-ALB Albany Intl
6h 21m1 stop Atlanta Hartsfield-Jackson
$277Delta
Sat, Sep 5 - Sun, Sep 6
Delta Logo
6:00 am - 9:07 amALB  Albany Intl-MDW Chicago Midway
4h 07m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:37 pm - 11:22 pmMDW  Chicago Midway-ALB Albany Intl
4h 45m1 stop Detroit Metropolitan Wayne County
$288Delta
Fri, Sep 11 - Sat, Sep 12
Delta Logo
8:55 am - 3:24 pmBOS  Boston Logan Intl-MDW Chicago Midway
7h 29m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:01 pm - 11:58 pmMDW  Chicago Midway-BOS Boston Logan Intl
3h 57m1 stop Detroit Metropolitan Wayne County
$315Delta
Sat, Sep 12 - Mon, Sep 14

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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
Sep 9
BOS7:30 amBoston Logan Intl
2h 35m
MDW9:05 amChicago Midway
Sep 12
MDW7:40 amChicago Midway
2h 20m
BOS11:00 amBoston Logan Intl
$207
Southwest
Sep 9
BOS8:30 amBoston Logan Intl
6h 00m
1 stop
MDW1:30 pmChicago Midway
Sep 12
MDW3:10 pmChicago Midway
2h 25m
BOS6:35 pmBoston Logan Intl
$217
Southwest
Oct 28
BOS5:55 pmBoston Logan Intl
2h 35m
MDW7:30 pmChicago Midway
Nov 4
MDW7:35 amChicago Midway
8h 35m
2 stops
BOS5:10 pmBoston Logan Intl
$222

Delta flights from Massachusetts to Chicago Midway Airport

Our best Delta deals on Massachusetts to Chicago Midway Airport flight tickets
Delta
Sep 11
ALB6:00 amAlbany Intl
4h 07m
1 stop
MDW9:07 amChicago Midway
Sep 12
MDW5:37 pmChicago Midway
4h 45m
1 stop
ALB11:22 pmAlbany Intl
$288
Delta
Sep 5
BDL1:09 pmHartford Bradley Intl
4h 50m
1 stop
MDW4:59 pmChicago Midway
Sep 8
MDW5:37 pmChicago Midway
4h 35m
1 stop
BDL11:12 pmHartford Bradley Intl
$316
Delta
Oct 27
ALB6:10 amAlbany Intl
6h 40m
1 stop
MDW11:50 amChicago Midway
Oct 30
MDW10:59 amChicago Midway
6h 12m
1 stop
ALB6:11 pmAlbany Intl
$317

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 August 8, 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
Quickest round-trip

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Wed 10/28

10:55 am-12:30 pm

Nonstop2h 35m

Chicago Midway

Tue 11/3

1:15 pm-4:20 pm

Nonstop2h 05m

$207

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Tue 9/15

10:05 am-11:35 am

Nonstop2h 30m

Chicago Midway

Tue 9/15

6:00 pm-9:25 pm

Nonstop2h 25m

$207

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Sat 9/12

8:40 am-10:15 am

Nonstop2h 35m

Chicago Midway

Tue 9/15

6:00 pm-9:25 pm

Nonstop2h 25m

$207

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Tue 10/27

10:55 am-12:30 pm

Nonstop2h 35m

Chicago Midway

Sat 10/31

4:05 pm-7:25 pm

Nonstop2h 20m

$207

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Wed 10/28

12:35 pm-9:53 pm

1 stop10h 18m

Chicago Midway

Mon 11/2

1:26 pm-10:42 am

1 stop20h 16m

$213

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Wed 10/21

11:28 am-9:58 pm

1 stop11h 30m

Chicago Midway

Mon 10/26

1:26 pm-10:42 am

1 stop20h 16m

$232

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Wed 10/21

11:28 am-9:58 pm

1 stop11h 30m

Chicago Midway

Fri 10/23

2:26 pm-8:12 am

1 stop16h 46m

$251

AlbanyChicago

ALB Albany Intl - MDW Chicago Midway

ALBMDW

Albany Intl

Sat 9/5

6:00 am-9:17 am

1 stop4h 17m

Chicago Midway

Sun 9/6

6:05 am-1:26 pm

1 stop6h 21m

$277

AlbanyChicago

ALB Albany Intl - MDW Chicago Midway

ALBMDW

Albany Intl

Fri 9/11

6:00 am-9:07 am

1 stop4h 07m

Chicago Midway

Sat 9/12

5:37 pm-11:22 pm

1 stop4h 45m

$288

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Sat 9/12

8:55 am-3:24 pm

1 stop7h 29m

Chicago Midway

Mon 9/14

7:01 pm-11:58 pm

1 stop3h 57m

$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 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 $162.

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 $346. 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 $454.

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 $296 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $397. 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 $274 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 $233 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

$185

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 $185. The best round-trip flight deal from Massachusetts to Chicago Midway Airport found on momondo in the last 72 hours is $262.
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
8,505 reviews
Search Delta flights
JetBluePriceFrom $117Free CancellationRating
7.1
3,030 reviews
Search JetBlue flights
SouthwestPriceFrom $135Free CancellationRating
8.0
4,216 reviews
Search Southwest flights
American AirlinesPriceFrom $181Free CancellationRating
7.1
11,885 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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