Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to Massachusetts from $59

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Massachusetts departing on 12/4. 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
0 bags

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

Find the cheapest flights from Chicago Midway Airport to Massachusetts

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:15 pm - 9:35 pmMDW-BOS
2h 20mnonstop
Southwest Logo
6:55 pm - 8:45 pmBOS-MDW
2h 50mnonstop
$117Southwest
Find Deal
Thu, Dec 4 - Sun, Dec 7
Southwest Logo
6:15 pm - 9:35 pmMDW-BOS
2h 20mnonstop
Southwest Logo
6:55 pm - 8:45 pmBOS-MDW
2h 50mnonstop
$122Southwest
Find Deal
Wed, Dec 3 - Sun, Dec 7
Southwest Logo
6:15 pm - 9:35 pmMDW-BOS
2h 20mnonstop
Southwest Logo
5:15 am - 7:00 amBOS-MDW
2h 45mnonstop
$124Southwest
Find Deal
Wed, Dec 24 - Sun, Dec 28
Southwest Logo
6:15 pm - 9:35 pmMDW-BOS
2h 20mnonstop
Southwest Logo
6:00 pm - 10:35 pmBOS-MDW
5h 35m1 stop
$127Southwest
Find Deal
Thu, Dec 4 - Thu, Dec 11
Multiple Airlines Logo
3:52 pm - 10:01 amMDW-BOS
17h 09m1 stop
Multiple Airlines Logo
6:00 am - 5:38 pmBOS-MDW
12h 38m1 stop
$128Multiple Airlines
Find Deal
Fri, Dec 5 - Thu, Jan 1
Frontier Logo
7:23 pm - 10:22 amMDW-BOS
13h 59m1 stop
Frontier Logo
11:28 am - 6:08 pmBOS-MDW
7h 40m1 stop
$129Frontier
Find Deal
Thu, Dec 4 - Thu, Dec 11
Frontier Logo
2:49 pm - 10:22 amMDW-BOS
18h 33m1 stop
Frontier Logo
11:23 am - 8:46 amBOS-MDW
22h 23m1 stop
$130Frontier
Find Deal
Wed, Dec 3 - Mon, Dec 8
Multiple Airlines Logo
3:52 pm - 10:01 amMDW-BOS
17h 09m1 stop
Multiple Airlines Logo
11:09 am - 10:12 pmBOS-MDW
12h 03m1 stop
$135Multiple Airlines
Find Deal
Fri, Dec 5 - Wed, Dec 31
Delta Logo
4:30 pm - 10:34 pmMDW-BDL
5h 04m1 stop
Delta Logo
5:30 am - 8:54 amBDL-MDW
4h 24m1 stop
$177Delta
Find Deal
Sat, Jan 31 - Sun, Feb 1
Delta Logo
9:34 am - 4:22 pmMDW-BDL
5h 48m1 stop
Delta Logo
5:30 am - 8:54 amBDL-MDW
4h 24m1 stop
$245Delta
Find Deal
Tue, Mar 3 - Wed, Mar 4

Frontier flights from Chicago Midway Airport to Massachusetts

Our best Frontier deals on Chicago Midway Airport to Massachusetts flight tickets
Frontier
Dec 4
MDW7:23 pmChicago Midway
13h 59m
1 stop
BOS10:22 amBoston Logan Intl
Dec 11
BOS11:28 amBoston Logan Intl
7h 40m
1 stop
MDW6:08 pmChicago Midway
$129
Find similar
Frontier
Dec 3
MDW2:49 pmChicago Midway
18h 33m
1 stop
BOS10:22 amBoston Logan Intl
Dec 8
BOS11:23 amBoston Logan Intl
22h 23m
1 stop
MDW8:46 amChicago Midway
$130
Find similar
Frontier
Jan 22
MDW6:00 amChicago Midway
18h 04m
1 stop
BOS1:04 amBoston Logan Intl
Jan 26
BOS6:00 amBoston Logan Intl
18h 25m
1 stop
MDW11:25 pmChicago Midway
$133
Find similar

Southwest flights from Chicago Midway Airport to Massachusetts

Our best Southwest deals on Chicago Midway Airport to Massachusetts flight tickets
Southwest
Dec 4
MDW6:15 pmChicago Midway
2h 20m
BOS9:35 pmBoston Logan Intl
Dec 7
BOS6:55 pmBoston Logan Intl
2h 50m
MDW8:45 pmChicago Midway
$117
Find similar
Southwest
Dec 3
MDW6:15 pmChicago Midway
2h 20m
BOS9:35 pmBoston Logan Intl
Dec 7
BOS6:55 pmBoston Logan Intl
2h 50m
MDW8:45 pmChicago Midway
$122
Find similar
Southwest
Dec 24
MDW6:15 pmChicago Midway
2h 20m
BOS9:35 pmBoston Logan Intl
Dec 28
BOS5:15 amBoston Logan Intl
2h 45m
MDW7:00 amChicago Midway
$124
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Massachusetts 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 November 4, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Massachusetts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 12/4

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Sun 12/7

6:55 pm-8:45 pm

Nonstop2h 50m

$117

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 12/3

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Sun 12/7

6:55 pm-8:45 pm

Nonstop2h 50m

$122

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 12/24

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Sun 12/28

5:15 am-7:00 am

Nonstop2h 45m

$124

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 12/4

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Thu 12/11

6:00 pm-10:35 pm

1 stop5h 35m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 12/5

3:52 pm-10:01 am

1 stop17h 09m

Boston Logan Intl

Thu 1/1

6:00 am-5:38 pm

1 stop12h 38m

$128

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 12/4

7:23 pm-10:22 am

1 stop13h 59m

Boston Logan Intl

Thu 12/11

11:28 am-6:08 pm

1 stop7h 40m

$129

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 12/3

2:49 pm-10:22 am

1 stop18h 33m

Boston Logan Intl

Mon 12/8

11:23 am-8:46 am

1 stop22h 23m

$130

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 12/5

3:52 pm-10:01 am

1 stop17h 09m

Boston Logan Intl

Wed 12/31

11:09 am-10:12 pm

1 stop12h 03m

$135

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Sat 1/31

4:30 pm-10:34 pm

1 stop5h 04m

Hartford Bradley Intl

Sun 2/1

5:30 am-8:54 am

1 stop4h 24m

$177

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Tue 3/3

9:34 am-4:22 pm

1 stop5h 48m

Hartford Bradley Intl

Wed 3/4

5:30 am-8:54 am

1 stop4h 24m

$245

Flights are sorted by cheapest round-trip flights first.

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

See travel insights to Massachusetts from

How to get the cheapest flight ticket from Chicago Midway Airport to Massachusetts

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 Massachusetts?

In general, January is the cheapest month to fly from Chicago Midway Airport to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $173. If you aren’t able to travel to Massachusetts during the month of January, then flying in March is also cheap. Prices for this month can be found on momondo for an average of $237.

What is the cheapest day to depart on your flight to Massachusetts?

According to our data, Tuesday is the cheapest day to fly to Massachusetts from Chicago Midway Airport. The lowest ticket price found for a Tuesday departure recently was $219. 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 Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $292.

What is the cheapest time of day to depart on your flight to Massachusetts?

Our data shows that the cheapest Chicago Midway Airport to Massachusetts flights are usually those with departure times in the afternoon. Our users have found flights to Massachusetts in the afternoon for as low as $223. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $287 on average. Flights to Massachusetts from Chicago Midway Airport at noon are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Chicago Midway to Massachusetts flight route?

Fly from Chicago Midway to Boston Logan Intl for the best Chicago Midway - Massachusetts flight prices

How far in advance should I book a flight to Massachusetts?

You are more likely to see cheaper flights to Massachusetts from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around $287 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from Chicago Midway Airport for as low as $183 on momondo.

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

There is only 1 cabin class available to choose from on Chicago Midway to Massachusetts flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap Chicago Midway Airport to Massachusetts flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Massachusetts

Best Price Found

$93

Fastest flight time

1h 50m

Direct flights

Every day

Airports in Massachusetts

2 airports
The best one-way flight to Massachusetts from Chicago Midway Airport in the past 72 hours is $93. The best round-trip flight deal from Chicago Midway Airport to Massachusetts found on momondo in the last 72 hours is $232.
The fastest flight from Chicago Midway Airport to Massachusetts takes 1h 50m
Direct flights go from Chicago Midway Airport to Massachusetts every day.
There are 2 airports near Massachusetts: Albany Intl (ALB), Hartford Bradley Intl (BDL)
Search flight deals

  • When did momondo last update prices for flights from Chicago Midway Airport to Massachusetts?

    Prices for flights from Chicago Midway Airport to Massachusetts are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago Midway Airport to Massachusetts?

  • How old do you have to be to fly from Chicago Midway Airport to Massachusetts?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Massachusetts.

  • What documentation or ID do you need to fly to Massachusetts?

    The travel and health documents required for your trip to Massachusetts can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Massachusetts. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Chicago Midway Airport to Massachusetts?

Best airlines flying from Chicago Midway Airport to Massachusetts

Compare and see reviews for airlines that fly from Chicago Midway Airport to Massachusetts with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $137Free CancellationRating
8.0
4,239 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Massachusetts?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Massachusetts from Chicago.

Can I find flights from Chicago to Massachusetts with flexible booking policies on momondo?

Yes. All flights to Massachusetts from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Massachusetts?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Massachusetts.

I’m not ready to book a flight from Chicago to Massachusetts right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Massachusetts now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Massachusetts and let you know when they change.

An easier way to manage your Massachusetts 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 12/4
Thu 12/11
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Massachusetts

Popular cities in Massachusetts

Popular flights according to clicks in the last 7 days on momondo
Flights to New Yorkfrom $49
Flights to Los Angelesfrom $49
Flights to Miamifrom $49
Flights to Chicagofrom $54
Flights to Orlandofrom $47
Flights to Las Vegasfrom $49
Flights to San Franciscofrom $54
Flights to Washington, D.C.from $54
Flights to Bostonfrom $40
Flights to Atlantafrom $40
Flights to Dallasfrom $49
Flights to Seattlefrom $68