Cheap flights from Boston (BOS) to Midway (MDW)

BOS — MDW
Dec 12 — Dec 191

How to find the cheapest flight from Boston (BOS) to Midway (MDW)

All the information you need to plan the best BOS to MDW flight in 2022: compare Boston to Midway flight prices with the expected peak season, weather and rainfall in Midway.

BOS - MDW

Price

$132 - $456

MDW

Temperature

23 - 73.4 °F

MDW

Rainfall

1.7 - 4.9 inches

Popular inJuneHigh demand for flights, 35% potential price rise
Cheapest inJanuaryBest time to find cheap flights, 56% potential price drop
Round-trip from$132From Boston Logan Intl to Chicago Midway
One-way from$72One-way flight from Boston Logan Intl to Chicago Midway

What is the cheapest month to fly from Boston to Chicago Midway Airport?

Flights from Boston to Chicago Midway Airport lean towards being more expensive in June. Prices are generally better when you fly from Boston to Chicago Midway Airport in January, with the cheapest ticket starting at $97.

When is the cheapest time to fly from Boston to Chicago Midway Airport (BOS - MDW)?

When flying from Boston to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap flights from Boston to Midway in December, January 2022

The best prices found for BOS to MDW flights for December, January
Dec 12 - Dec 13
BOS

Boston Logan Intl

MDW

Chicago Midway

Nonstop

2h 50m
MDW

Chicago Midway

BOS

Boston Logan Intl

Nonstop

2h 20m
$140

Southwest

Pick Dates

Deal found 12/5

Dec 12 - Dec 13
BOS

Boston Logan Intl

MDW

Chicago Midway

1 stop

21h 05m
MDW

Chicago Midway

BOS

Boston Logan Intl

1 stop

20h 36m
$144

Frontier

Pick Dates

Deal found 12/6

Dec 12 - Dec 13
BOS

Boston Logan Intl

MDW

Chicago Midway

Nonstop

2h 50m
MDW

Chicago Midway

BOS

Boston Logan Intl

1 stop

5h 50m
$149

Southwest

Pick Dates

Deal found 12/5

Boston to Midway 2022 flight deals

Cheap flights to Midway from Boston found for this year
Dec 12 - Dec 13
BOS

Boston Logan Intl

MDW

Chicago Midway

Nonstop

2h 50m
MDW

Chicago Midway

BOS

Boston Logan Intl

Nonstop

2h 20m
$140

Southwest

Pick Dates

Deal found 12/5

Dec 12 - Dec 13
BOS

Boston Logan Intl

MDW

Chicago Midway

1 stop

21h 05m
MDW

Chicago Midway

BOS

Boston Logan Intl

1 stop

20h 36m
$144

Frontier

Pick Dates

Deal found 12/6

Dec 12 - Dec 13
BOS

Boston Logan Intl

MDW

Chicago Midway

Nonstop

2h 50m
MDW

Chicago Midway

BOS

Boston Logan Intl

1 stop

5h 50m
$149

Southwest

Pick Dates

Deal found 12/5

Cheap Frontier flights from Boston to Midway

Dec 12 - Dec 13
BOS

Boston Logan Intl

MDW

Chicago Midway

1 stop

21h 05m
MDW

Chicago Midway

BOS

Boston Logan Intl

1 stop

20h 36m
$144

Frontier

Pick Dates

Deal found 12/6

Feb 10 - Feb 12
BOS

Boston Logan Intl

MDW

Chicago Midway

1 stop

10h 24m
MDW

Chicago Midway

BOS

Boston Logan Intl

1 stop

11h 12m
$165

Frontier

Pick Dates

Deal found 12/5

Dec 13 - Dec 15
BOS

Boston Logan Intl

MDW

Chicago Midway

1 stop

16h 43m
MDW

Chicago Midway

BOS

Boston Logan Intl

1 stop

15h 29m
$169

Frontier

Pick Dates

Deal found 12/5

Cheap Southwest flights from Boston to Midway

Dec 12 - Dec 13
BOS

Boston Logan Intl

MDW

Chicago Midway

Nonstop

2h 50m
MDW

Chicago Midway

BOS

Boston Logan Intl

Nonstop

2h 20m
$140

Southwest

Pick Dates

Deal found 12/5

Dec 12 - Dec 13
BOS

Boston Logan Intl

MDW

Chicago Midway

Nonstop

2h 50m
MDW

Chicago Midway

BOS

Boston Logan Intl

1 stop

5h 50m
$149

Southwest

Pick Dates

Deal found 12/5

Dec 12 - Dec 13
BOS

Boston Logan Intl

MDW

Chicago Midway

2 stops

11h 00m
MDW

Chicago Midway

BOS

Boston Logan Intl

Nonstop

2h 20m
$154

Southwest

Pick Dates

Deal found 12/5

Non-stop flights to Midway from Boston

Save time with Boston to Midway direct flight deals
Mar 12 - Mar 29
BOS

Boston Logan Intl

MDW

Chicago Midway

Nonstop

2h 45m
MDW

Chicago Midway

BOS

Boston Logan Intl

Nonstop

2h 10m
$170

Southwest

Pick Dates

Deal found 12/5

Jan 8 - Jan 11
BOS

Boston Logan Intl

MDW

Chicago Midway

Nonstop

2h 45m
MDW

Chicago Midway

BOS

Boston Logan Intl

Nonstop

2h 10m
$196

Southwest

Pick Dates

Deal found 12/6

Last minute flights from Boston to Midway

Late deals on return flights to Midway from Boston, departing today and this week
Dec 12 - Dec 13
BOS

Boston Logan Intl

MDW

Chicago Midway

Nonstop

2h 50m
MDW

Chicago Midway

BOS

Boston Logan Intl

Nonstop

2h 20m
$140

Southwest

Pick Dates

Deal found 12/5

Dec 12 - Dec 13
BOS

Boston Logan Intl

MDW

Chicago Midway

1 stop

21h 05m
MDW

Chicago Midway

BOS

Boston Logan Intl

1 stop

20h 36m
$144

Frontier

Pick Dates

Deal found 12/6

Dec 12 - Dec 13
BOS

Boston Logan Intl

MDW

Chicago Midway

Nonstop

2h 50m
MDW

Chicago Midway

BOS

Boston Logan Intl

1 stop

5h 50m
$149

Southwest

Pick Dates

Deal found 12/5

One-way flights to Midway from Boston

The cheapest one-way flights from Boston to Midway
Dec 12
BOS

Boston Logan Intl

MDW

Chicago Midway

1 stop

21h 05m
$56

Frontier

Pick Dates

Deal found 12/5

Dec 12
BOS

Boston Logan Intl

MDW

Chicago Midway

1 stop

21h 05m
$67

Frontier

Pick Dates

Deal found 12/6

Jan 17
BOS

Boston Logan Intl

MDW

Chicago Midway

1 stop

19h 09m
$71

Multiple Airlines

Pick Dates

Deal found 12/5

Related info for your journey

Useful info, stats and facts about Boston to Midway flights.

What airport do you fly from for flights from Boston to Chicago Midway?

If you book a flight to Chicago Midway from Boston, you will be flying from Logan Intl, which is the city’s only airport. Boston Logan Intl (BOS) is located 2.6 mi from the center of Boston. There are 2 flights from Logan Intl to Chicago Midway per day from 7 different airlines.

Which airlines flying from Boston Logan Intl to Chicago Midway have flexible cancellations due to COVID-19?

Some of our airline partners flying from Boston Logan Intl to Chicago Midway have new flexible policies in place due to COVID-19. Delta, American Airlines, and United Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like Delta with this kind of flexibility.

Can I find flights from Boston to Chicago Midway Airport for under $200 on Cheapflights?

Yes, there are multiple flights from Boston to Chicago Midway Airport for under $200. The cheapest flight booked recently is on Multiple Airlines for just $157, but on average you can expect to pay $192.

Are there nonstop flights from Boston to Chicago Midway Airport for under $200 on Cheapflights?

Cheapflights has at least 2 direct flights from Boston to Chicago Midway Airport under $200. A good price for a nonstop flight from Boston to Chicago Midway Airport is less than $183.

Are there last-minute flights available from Boston to Chicago Midway Airport for under $200?

There are currently 20+ open flights from Boston to Chicago Midway Airport within the next 7 days for less than $200.

What days are nonstop flights available from Boston to Chicago Midway Airport?

Nonstop flights are available for this route on the following days: Friday.

How many flights depart from Boston to Chicago Midway Airport on average per day?

Travelers can expect 1 flight from Boston to Chicago Midway Airport on average per day.
Early Morning (Midnight to 6am) - 100% of flight departures

How long is the flight from Boston to Chicago Midway Airport?

Frontier and Southwest can get you from Boston to Chicago Midway Airport in just under 2h 45m. Your travel time can differ by up to 7h 39m. Boston and Chicago Midway Airport are separated by a distance of 863 mi. Both multi-stop and nonstop flights can be found to your destination and back.

What are the cheapest airlines flying from Boston to Chicago Midway Airport round-trip?

According to our current data, Frontier ($165), and Southwest ($170) offers the cheapest pricing from Boston to Chicago Midway Airport. You may be able to fly from Boston to Chicago Midway Airport for 44% less than the average price by searching for these airlines.

What are the cheapest airlines to fly from Boston to Chicago Midway Airport one-way?

The cheapest airlines for a one-way flight from Boston to Chicago Midway Airport are Frontier ($56), Delta ($72), and Allegiant Air ($131).

What are the most popular airlines that fly from Boston to Chicago Midway Airport?

When booking a flight from Boston to Chicago Midway Airport, you may want to consider flying on American Airlines, Alaska Airlines or JetBlue as they are the most popular for this route.

What are the cheapest flights from Boston to Chicago Midway Airport?

Looking for the cheapest flight from Boston to Chicago Midway Airport? While on average our users pay $394, our data indicates the cheapest price to be $79. The most popular route (Boston Logan Intl - Chicago Midway), is priced around $165.

Alternative routes for Boston to Midway

See prices for flight routes from nearby airports that may be better suited for you.

Top 4 airlines flying from Boston to Midway

The chart below displays the airlines Cheapflights users traveling from Boston to Midway choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
United AirlinesCheapest$88Average$259FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
DeltaCheapest$115Average$396FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
American AirlinesCheapest$194Average$302FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
Alaska AirlinesCheapest$366Average$377FlexibilityNo cancel feeOn-time75%COVID-19 safety
Search Alaska Airlines flights

Hourly flight availability from Boston to Midway

See what time of day planes typically take off from Boston to Midway
11%of flight departuresEarly morningMidnight to 6 am
29%of flight departuresMorning6 am to noon
35%of flight departuresAfternoonNoon to 6 pm
25%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Boston to Midway

See how many times per day planes take to the skies headed from Boston to Midway
Sunday0daily flights
Monday4daily flights
Tuesday4daily flights
Wednesday4daily flights
Thursday4daily flights
Friday4daily flights
Saturday0daily flights