$104 Find Cheap Flights from Chicago Midway Airport to Massachusetts - Compare and Save

The cheapest ticket to Massachusetts from Chicago Midway Airport found in the last 5 days was to Boston, at $157 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Boston (BOS), and the cheapest round-trip airline ticket found on this route in the last 5 days was $157.

The cheapest time of day to fly to Massachusetts is generally in the evening, when round-trip flights cost $251 on average. Morning departures are around 12% more expensive than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally in the morning, which is peak travel time and where the average cost of a ticket is $280.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $174 on average.

The cheapest month for flights from Chicago Midway Airport to Massachusetts is September, when tickets cost $263 (return) on average. On the other hand, the most expensive months are January and June, when the average cost of round-trip tickets is $414 and $335 respectively.

If your flying dates are flexible, you should consider flying to Massachusetts on a Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Chicago Midway Airport to Massachusetts. For your return ticket, we recommend flying on a Thursday and avoiding Sundays for the best deals.

To get a below average price on the flight from Chicago Midway Airport to Massachusetts, you should book around 3 weeks before departure, which saves you about 40% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

There is just one airline that flies from Chicago Midway Airport to Massachusetts direct and that is Southwest. The best round-trip deal found from Southwest for the route is to Boston (BOS) and costs $126.

In the past 5 days, the cheapest round-trip tickets from Chicago Midway Airport to Massachusetts were found on Southwest ($216) and Delta ($297).

The duration of a flight to Massachusetts depends on your arrival airport. The shortest routes to Massachusetts from Chicago Midway Airport are to Boston, which takes 2h 15m, and Boston, which takes 7h 30m.

There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

The earliest flight from Chicago Midway Airport to Massachusetts departs at 5:15 am, landing in Boston at 8:25 am.

If you prefer to fly at night, the latest flight from Chicago Midway Airport to Massachusetts jets off at 7:35 pm and lands in Boston at 10:55 pm.