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Cheap flights from Massachusetts to Chicago from $69

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 10/23. 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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0 bags

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Find the cheapest flights from Massachusetts to Chicago

Cheap round-trip flights

Southwest Logo
5:35 am - 9:00 amBOS-MDW
4h 25m1 stop
Southwest Logo
7:15 am - 4:25 pmMDW-BOS
8h 10m1 stop
$132Southwest
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Thu, Sep 18 - Mon, Sep 22
Southwest Logo
5:15 am - 6:45 amBOS-MDW
2h 30mnonstop
Southwest Logo
6:45 pm - 10:05 pmMDW-BOS
2h 20mnonstop
$137Southwest
Find Deal
Thu, Sep 18 - Mon, Sep 22
Frontier Logo
9:28 am - 7:11 amBOS-MDW
22h 43m1 stop
Frontier Logo
6:15 am - 9:58 amMDW-BOS
26h 43m1 stop
$161Frontier
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Thu, Sep 4 - Sat, Sep 6
Frontier Logo
10:53 am - 3:58 pmBOS-MDW
6h 05m1 stop
Frontier Logo
5:15 pm - 7:43 amMDW-BOS
13h 28m1 stop
$166Frontier
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Thu, Sep 4 - Fri, Sep 5
Logo
12:20 pm - 9:18 amBOS-MDW
21h 58m1 stop
Logo
6:21 am - 11:13 amMDW-BOS
27h 52m2 stops
$210
Find Deal
Sat, Sep 6 - Mon, Sep 8
Logo
2:53 pm - 9:51 amBOS-MDW
19h 58m1 stop
Logo
2:32 pm - 10:47 pmMDW-BOS
31h 15m2 stops
$211
Find Deal
Fri, Sep 19 - Tue, Sep 23
Allegiant Air Logo
8:59 am - 4:43 pmBOS-MDW
8h 44m1 stop
Allegiant Air Logo
7:50 pm - 9:43 amMDW-BOS
12h 53m1 stop
$221Allegiant Air
Find Deal
Fri, Sep 5 - Mon, Sep 8
Allegiant Air Logo
8:59 am - 4:43 pmBOS-MDW
8h 44m1 stop
Allegiant Air Logo
7:50 pm - 9:43 amMDW-BOS
12h 53m1 stop
$224Allegiant Air
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Fri, Sep 5 - Mon, Sep 8
Delta Logo
6:08 am - 8:40 amALB-MDW
3h 32m1 stop
Delta Logo
5:59 pm - 11:08 pmMDW-ALB
4h 09m1 stop
$237Delta
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Wed, Oct 29 - Tue, Nov 11
Delta Logo
6:00 am - 1:03 pmBDL-MDW
8h 03m1 stop
Delta Logo
6:00 am - 1:31 pmMDW-BDL
6h 31m1 stop
$245Delta
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Sat, Sep 13 - Tue, Sep 16

Allegiant Air flights from Massachusetts to Chicago Midway Airport

Our best Allegiant Air deals on Massachusetts to Chicago Midway Airport flight tickets
Allegiant Air
Sep 5
BOS8:59 amBoston Logan Intl
8h 44m
1 stop
MDW4:43 pmChicago Midway
Sep 8
MDW7:50 pmChicago Midway
12h 53m
1 stop
BOS9:43 amBoston Logan Intl
$221
Find similar
Allegiant Air
Sep 5
BOS8:59 amBoston Logan Intl
8h 44m
1 stop
MDW4:43 pmChicago Midway
Sep 8
MDW7:50 pmChicago Midway
12h 53m
1 stop
BOS9:43 amBoston Logan Intl
$224
Find similar
Allegiant Air
Sep 5
BOS8:59 amBoston Logan Intl
8h 44m
1 stop
MDW4:43 pmChicago Midway
Sep 8
MDW7:50 pmChicago Midway
12h 53m
1 stop
BOS9:43 amBoston Logan Intl
$226
Find similar

Southwest flights from Massachusetts to Chicago Midway Airport

Our best Southwest deals on Massachusetts to Chicago Midway Airport flight tickets
Southwest
Sep 18
BOS5:35 amBoston Logan Intl
4h 25m
1 stop
MDW9:00 amChicago Midway
Sep 22
MDW7:15 amChicago Midway
8h 10m
1 stop
BOS4:25 pmBoston Logan Intl
$132
Find similar
Southwest
Sep 18
BOS5:15 amBoston Logan Intl
2h 30m
MDW6:45 amChicago Midway
Sep 22
MDW6:45 pmChicago Midway
2h 20m
BOS10:05 pmBoston Logan Intl
$137
Find similar
Southwest
Sep 22
BOS5:35 amBoston Logan Intl
8h 35m
2 stops
MDW1:10 pmChicago Midway
Sep 24
MDW6:25 amChicago Midway
8h 00m
1 stop
BOS3:25 pmBoston Logan Intl
$138
Find similar

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 20, 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

Thu 9/18

5:35 am-9:00 am

1 stop4h 25m

Chicago Midway

Mon 9/22

7:15 am-4:25 pm

1 stop8h 10m

$132

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 9/18

5:15 am-6:45 am

Nonstop2h 30m

Chicago Midway

Mon 9/22

6:45 pm-10:05 pm

Nonstop2h 20m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 9/4

9:28 am-7:11 am

1 stop22h 43m

Chicago Midway

Sat 9/6

6:15 am-9:58 am

1 stop26h 43m

$161

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 9/4

10:53 am-3:58 pm

1 stop6h 05m

Chicago Midway

Fri 9/5

5:15 pm-7:43 am

1 stop13h 28m

$166

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 9/6

12:20 pm-9:18 am

1 stop21h 58m

Chicago Midway

Mon 9/8

6:21 am-11:13 am

2 stops27h 52m

$210

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 9/19

2:53 pm-9:51 am

1 stop19h 58m

Chicago Midway

Tue 9/23

2:32 pm-10:47 pm

2 stops31h 15m

$211

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 9/5

8:59 am-4:43 pm

1 stop8h 44m

Chicago Midway

Mon 9/8

7:50 pm-9:43 am

1 stop12h 53m

$221

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 9/5

8:59 am-4:43 pm

1 stop8h 44m

Chicago Midway

Mon 9/8

7:50 pm-9:43 am

1 stop12h 53m

$224

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Wed 10/29

6:08 am-8:40 am

1 stop3h 32m

Chicago Midway

Tue 11/11

5:59 pm-11:08 pm

1 stop4h 09m

$237

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 9/13

6:00 am-1:03 pm

1 stop8h 03m

Chicago Midway

Tue 9/16

6:00 am-1:31 pm

1 stop6h 31m

$245

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 $200. 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 $206.

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 $291. 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 $424.

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 $315 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $341. 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 $252 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 $170 on momondo.

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

There are 1 cabin classes 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

$162

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 $162. The best round-trip flight deal from Massachusetts to Chicago Midway Airport found on momondo in the last 72 hours is $194.
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

  • 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
United AirlinesPriceFrom $97Free CancellationRating
7.4
8,928 reviews
Search United Airlines flights
FrontierPriceFrom $100Free CancellationRating
5.8
3,207 reviews
Search Frontier flights
SouthwestPriceFrom $120Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
DeltaPriceFrom $227Free CancellationRating
7.9
7,982 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.

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