When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 55 days in advance, which can save you up to 24% on flights from Massachusetts to Chicago Midway Airport compared to booking the week you need them. Waiting 55 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $237. For sooner than that we have options available in the next 3 days from $310.
Due to multiple factors, expect to potentially pay more when booking in June. For low rates, January can be a great choice for travel to Chicago Midway Airport. Flights to Chicago Midway Airport from Massachusetts in January are about $260 on average during January, but can be found for as low as $79.
When flying from Massachusetts 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.
Fly from
Fly to
Budget
$97 - $310
Route
Depart
Return
Price
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 5/11
1 stop11h 00m
Chicago Midway
Sat 5/18
1 stop11h 35m
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 5/11
1 stop11h 00m
Chicago Midway
Sat 5/18
1 stop11h 35m
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 5/15
1 stop11h 44m
Chicago Midway
Sun 5/19
1 stop24h 15m
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 5/8
1 stop11h 44m
Chicago Midway
Sat 5/11
1 stop10h 51m
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 5/8
1 stop11h 44m
Chicago Midway
Sat 5/18
1 stop11h 35m
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 5/15
1 stop11h 44m
Chicago Midway
Sun 5/19
1 stop24h 15m
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 5/25
1 stop7h 58m
Chicago Midway
Wed 5/29
1 stop23h 51m
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Sun 6/16
Nonstop2h 35m
Chicago Midway
Sat 6/22
Nonstop2h 15m
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 5/15
1 stop4h 35m
Chicago Midway
Sat 5/18
1 stop12h 57m
No data available for this route at this time. Please check back soon.
Crew
Overall
Entertainment
Food
Boarding
Comfort
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Crew
Overall
Entertainment
Food
Boarding
Comfort
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Crew
Overall
Entertainment
Food
Boarding
Comfort
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Crew
Overall
Entertainment
Food
Boarding
Comfort
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Crew
Overall
Entertainment
Food
Boarding
Comfort
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
1%of flight departures | Early morningMidnight to 6 am |
---|---|
53%of flight departures | Morning6 am to noon |
15%of flight departures | AfternoonNoon to 6 pm |
31%of flight departures | Evening6 pm to midnight |
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