How many flights depart from Chicago Midway Airport to Massachusetts on average per week?

4 flights are operational weekly from Chicago Midway Airport to Massachusetts as of October 2026. The most popular departure day for this route is Wed, with 100% of flights per week taking off on this day.

What is the cheapest airline that flies from Chicago Midway to Massachusetts?

Southwest and Delta are the most popular carriers operating from Chicago Midway to Massachusetts

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?

As of October 2026, there is 1 operator available to choose from 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.

$115 Cheap Flights from Chicago Midway Airport to Massachusetts in 2026/27

Find the cheapest flights from Chicago Midway Airport to Massachusetts

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

4:45 pm - 10:45 pmMDW Chicago Midway-BOS Boston Logan Intl

5h 00m1 stop Baltimore/Washington

5:55 pm - 7:40 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 45mnonstop

$219Southwest

Wed, Oct 28 - Wed, Nov 4

1:10 pm - 4:30 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

5:35 am - 11:20 amBOS Boston Logan Intl-MDW Chicago Midway

6h 45m1 stop Baltimore/Washington

$219Southwest

Wed, Oct 21 - Tue, Oct 27

6:10 pm - 9:30 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

5:05 pm - 9:35 pmBOS Boston Logan Intl-MDW Chicago Midway

5h 30m1 stop Lambert-St Louis

$219Southwest

Tue, Oct 27 - Wed, Nov 4

7:50 am - 11:10 amMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

4:15 pm - 10:15 pmBOS Boston Logan Intl-MDW Chicago Midway

7h 00m1 stop Nashville Intl

$219Southwest

Tue, Oct 20 - Tue, Oct 27

1:10 pm - 4:30 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

5:30 pm - 11:50 pmBOS Boston Logan Intl-MDW Chicago Midway

7h 20m1 stop Dallas Love Field

$219Southwest

Tue, Oct 27 - Wed, Oct 28

3:50 pm - 9:45 pmMDW Chicago Midway-BOS Boston Logan Intl

4h 55m1 stop Lambert-St Louis

7:10 am - 8:55 amBOS Boston Logan Intl-MDW Chicago Midway

2h 45mnonstop

$219Southwest

Wed, Nov 11 - Wed, Nov 18

3:15 pm - 6:35 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

2:25 pm - 7:05 pmBOS Boston Logan Intl-MDW Chicago Midway

5h 40m1 stop Nashville Intl

$219Southwest

Wed, Oct 14 - Wed, Nov 4

1:15 pm - 4:20 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 05mnonstop

5:45 pm - 10:45 pmBOS Boston Logan Intl-MDW Chicago Midway

6h 00m1 stop Nashville Intl

$219Southwest

Wed, Nov 11 - Wed, Nov 11

9:37 pm - 10:13 amMDW Chicago Midway-BOS Boston Logan Intl

11h 36m1 stop Orlando

11:08 am - 8:42 pmBOS Boston Logan Intl-MDW Chicago Midway

10h 34m1 stop Orlando

$234Frontier

Fri, Dec 11 - Sun, Dec 13

9:37 pm - 10:13 amMDW Chicago Midway-BOS Boston Logan Intl

11h 36m1 stop Orlando

11:08 am - 8:42 pmBOS Boston Logan Intl-MDW Chicago Midway

10h 34m1 stop Orlando

$234Frontier

Thu, Dec 10 - Sun, Dec 13

Cheap last minute flights

Enter your travel dates to find the best prices.

1:10 pm - 4:30 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

10:55 am - 12:30 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

$316Southwest

Wed, Oct 7 - Tue, Oct 13

1:10 pm - 4:30 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

10:55 am - 12:30 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

$316Southwest

Wed, Oct 7 - Tue, Oct 13

7:50 am - 3:35 pmMDW Chicago Midway-BOS Boston Logan Intl

6h 45m1 stop Kansas City

10:55 am - 12:30 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

$326Southwest

Wed, Oct 7 - Tue, Oct 13

7:50 am - 3:35 pmMDW Chicago Midway-BOS Boston Logan Intl

6h 45m1 stop Kansas City

10:55 am - 12:30 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

$326Southwest

Wed, Oct 7 - Tue, Oct 13

7:55 am - 4:05 pmMDW Chicago Midway-BOS Boston Logan Intl

7h 10m2 stops Raleigh-Durham Baltimore/Washington

10:55 am - 12:30 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

$331Southwest

Wed, Oct 7 - Tue, Oct 13

7:55 am - 4:05 pmMDW Chicago Midway-BOS Boston Logan Intl

7h 10m2 stops Raleigh-Durham Baltimore/Washington

10:55 am - 12:30 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

$331Southwest

Wed, Oct 7 - Tue, Oct 13

6:10 pm - 9:30 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

10:55 am - 12:30 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

$337Southwest

Tue, Oct 6 - Tue, Oct 13

1:10 pm - 4:30 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

10:55 am - 12:30 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

$337Southwest

Wed, Oct 7 - Tue, Oct 13

1:19 pm - 7:46 pmMDW Chicago Midway-BOS Boston Logan Intl

5h 27m1 stop Detroit Metropolitan Wayne County

5:50 am - 11:47 amBOS Boston Logan Intl-MDW Chicago Midway

6h 57m1 stop Minneapolis St Paul

$396Delta

Fri, Oct 2 - Sun, Nov 8

10:48 am - 6:00 pmMDW Chicago Midway-BOS Boston Logan Intl

6h 12m1 stop Atlanta Hartsfield-Jackson

5:30 am - 10:03 amBOS Boston Logan Intl-MDW Chicago Midway

5h 33m1 stop Atlanta Hartsfield-Jackson

$417Delta

Mon, Oct 5 - Thu, Oct 8

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Southwest flights from Chicago Midway Airport to Massachusetts

Our best Southwest deals on Chicago Midway Airport to Massachusetts flight tickets

Southwest

Oct 27

MDW6:10 pmChicago Midway

2h 20m

BOS9:30 pmBoston Logan Intl

Nov 4

BOS5:05 pmBoston Logan Intl

5h 30m

1 stop

MDW9:35 pmChicago Midway

$219

Southwest

Oct 14

MDW3:15 pmChicago Midway

2h 20m

BOS6:35 pmBoston Logan Intl

Oct 15

BOS5:50 amBoston Logan Intl

2h 35m

MDW7:25 amChicago Midway

$222

Southwest

Oct 27

MDW3:05 pmChicago Midway

6h 40m

2 stops

BOS10:45 pmBoston Logan Intl

Nov 3

BOS5:55 pmBoston Logan Intl

2h 45m

MDW7:40 pmChicago Midway

$224

Delta flights from Chicago Midway Airport to Massachusetts

Our best Delta deals on Chicago Midway Airport to Massachusetts flight tickets

Delta

Oct 14

MDW6:44 pmChicago Midway

4h 15m

1 stop

BOS11:59 pmBoston Logan Intl

Oct 20

BOS5:39 amBoston Logan Intl

4h 53m

1 stop

MDW9:32 amChicago Midway

$317

Delta

Oct 10

MDW6:44 pmChicago Midway

4h 15m

1 stop

BOS11:59 pmBoston Logan Intl

Oct 13

BOS1:05 pmBoston Logan Intl

5h 55m

1 stop

MDW6:00 pmChicago Midway

$327

Delta

Oct 11

MDW12:27 pmChicago Midway

5h 27m

1 stop

BOS6:54 pmBoston Logan Intl

Oct 13

BOS9:15 amBoston Logan Intl

4h 32m

1 stop

MDW12:47 pmChicago Midway

$335

momondo Fare Finder

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

Cheapest round-trip

ChicagoBoston

MDW Chicago Midway - BOS Boston Logan Intl

MDWBOS

Chicago Midway

Wed 10/28

4:45 pm-10:45 pm

1 stop5h 00m

Boston Logan Intl

Wed 11/4

5:55 pm-7:40 pm

Nonstop2h 45m

$219

ChicagoBoston

MDW Chicago Midway - BOS Boston Logan Intl

MDWBOS

Chicago Midway

Wed 10/21

1:10 pm-4:30 pm

Nonstop2h 20m

Boston Logan Intl

Tue 10/27

5:35 am-11:20 am

1 stop6h 45m

$219

ChicagoBoston

MDW Chicago Midway - BOS Boston Logan Intl

MDWBOS

Chicago Midway

Tue 10/27

6:10 pm-9:30 pm

Nonstop2h 20m

Boston Logan Intl

Wed 11/4

5:05 pm-9:35 pm

1 stop5h 30m

$219

ChicagoBoston

MDW Chicago Midway - BOS Boston Logan Intl

MDWBOS

Chicago Midway

Tue 10/20

7:50 am-11:10 am

Nonstop2h 20m

Boston Logan Intl

Tue 10/27

4:15 pm-10:15 pm

1 stop7h 00m

$219

ChicagoBoston

MDW Chicago Midway - BOS Boston Logan Intl

MDWBOS

Chicago Midway

Tue 10/27

1:10 pm-4:30 pm

Nonstop2h 20m

Boston Logan Intl

Wed 10/28

5:30 pm-11:50 pm

1 stop7h 20m

$219

Quickest round-trip

ChicagoBoston

MDW Chicago Midway - BOS Boston Logan Intl

MDWBOS

Chicago Midway

Wed 11/11

3:50 pm-9:45 pm

1 stop4h 55m

Boston Logan Intl

Wed 11/18

7:10 am-8:55 am

Nonstop2h 45m

$219

ChicagoBoston

MDW Chicago Midway - BOS Boston Logan Intl

MDWBOS

Chicago Midway

Wed 10/14

3:15 pm-6:35 pm

Nonstop2h 20m

Boston Logan Intl

Wed 11/4

2:25 pm-7:05 pm

1 stop5h 40m

$219

ChicagoBoston

MDW Chicago Midway - BOS Boston Logan Intl

MDWBOS

Chicago Midway

Wed 11/11

1:15 pm-4:20 pm

Nonstop2h 05m

Boston Logan Intl

Wed 11/11

5:45 pm-10:45 pm

1 stop6h 00m

$219

ChicagoBoston

MDW Chicago Midway - BOS Boston Logan Intl

MDWBOS

Chicago Midway

Fri 12/11

9:37 pm-10:13 am

1 stop11h 36m

Boston Logan Intl

Sun 12/13

11:08 am-8:42 pm

1 stop10h 34m

$234

ChicagoBoston

MDW Chicago Midway - BOS Boston Logan Intl

MDWBOS

Chicago Midway

Thu 12/10

9:37 pm-10:13 am

1 stop11h 36m

Boston Logan Intl

Sun 12/13

11:08 am-8:42 pm

1 stop10h 34m

$234

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

What is the cheapest month to fly to Massachusetts?

In general, December 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 $267. If you aren’t able to travel to Massachusetts during the month of December, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $277.

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

According to our data, Friday is the cheapest day to fly to Massachusetts from Chicago Midway Airport. The lowest ticket price found for a Friday departure recently was $260. 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, Monday 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 $337.

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 at noon. Our users have found flights to Massachusetts at noon for as low as $261. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $301 on average. Flights to Massachusetts from Chicago Midway Airport in the morning 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 from Chicago Midway Airport 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 $336 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 $246 on momondo.

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

There is only 1 cabin class available to choose from on Chicago Midway Airport 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	$115
Fastest flight time	1h 50m
Direct flights	Every day
Airports in Massachusetts	140 airports

The best one-way flight to Massachusetts from Chicago Midway Airport in the past 72 hours is $115. The best round-trip flight deal from Chicago Midway Airport to Massachusetts found on momondo in the last 72 hours is $219.

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 140 airports in Massachusetts. From Chicago Midway Airport there are direct flights to Boston Logan Intl (BOS).

Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Massachusetts

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?
As of October 2026, there is 1 operator available to choose from 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?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago Midway Airport to Massachusetts is Boeing 737 MAX 8 (16.17% of total bookings). The next most popular plane models are Airbus A220-300 (15.44%), Boeing 737-800 (14.05%), and Boeing 737 MAX 9 (9.73%).

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
Southwest	PriceFrom $141	Free Cancellation	Rating 8.0 4,212 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.