Skip to main content
Beginning of main content

Cheap Flights from Chicago to Boston $186.82

Search over 282,000 hotels worldwide and 400 airlines worldwide.
Secure incredible value with Expedia’s Price Pledge
No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheapest Flights from Chicago to Boston (MDW to BOS)

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Interesting Facts About Flights from Chicago to Boston (MDW to BOS)

Question : Which airline has been on time to Logan International Airport (BOS) from Chicago Midway International Airport (MDW) the most?
Answer : The current leader is Executive Jet Management with a 100% on-time rate. Stick to Executive Jet Management and you won't spend more time in airports than you have to. Perfection is hard to come by, so hopefully it continues.

Question : On a daily basis, how many different flight times can you take from Chicago Midway International Airport (MDW) to Logan International Airport (BOS)?
Answer : On average, you can expect 13 different options of flight times when you book. You won't have as many choices on this route as most others.

Question : Who's offering the cheapest round-trip flight to Logan International Airport (BOS) over the coming months?
Answer : Delta Air Lines is offering its passengers the cheapest flights over the next three months.

Question : Is there an alternative to Chicago Midway International Airport (MDW) for getting you to Boston?
Answer : Try looking for flights from O'Hare International Airport (ORD) as well. Over the upcoming months, flights from ORD to BOS are being priced 34% cheaper than flights from MDW to BOS. Being only 16 miles away, it's easily accessible for most.

Question : If having the most departure times is important to you, are there particular days that offer more options than others?
Answer : With 67 total flight time options, Wednesday provides the most flexibility from MDW to BOS. The days with the least number of times are Sunday and Friday with 48 options.

Question : Can you cut down on flight costs by changing the day of the week you travel to Boston?
Answer : In December, Thursday is your lowest-cost day to fly. Being flexible with your travel days garners you even more savings during your booking.