MDW to BOS (Chicago to Boston) Flights

Last Minute Flights from MDW to BOS

Price found within the past 7 days for the specified period. Click for updated prices.

OriginDestinationTravel DatesFlights From*
MDWBostonMay 3 to May 14$253
*Prices include taxes and fees

Cheapest MDW to BOS Flights

Price found within the past 7 days for the specified period. Click for updated prices.

OriginDestinationTravel DatesFlights From*
MDWBostonJune 18 to June 18$111
MDWBostonJune 5 to June 9$117
MDWBostonJune 1 to June 4$218
MDWBostonJuly 3 to July 6$317
*Prices include taxes and fees
MDW to BOS Flight Details
Origin airport
Midway Intl.
Origin airport IATA code
MDW
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Distance
857 mi

Frequently asked questions

What airlines fly direct from Chicago Airport to Logan Intl. Airport (BOS)?
To make your way from MDW to Logan Intl. Airport (BOS), you’ll have to book a flight with at least one stop. At the moment, there are no nonstop services on this particular route.
How many flights are there from MDW to BOS?
Around 3 a day. If you’re in a hurry to visit Boston, see if you can grab an epic last-minute deal from Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan Intl.) and then lock it in fast!
How long does it take to fly from Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan Intl.)?
The flight length from Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan Intl.) is approximately 2 hours and 15 minutes. The in-flight entertainment system isn’t always available on quick trips, so bring a magazine to read or download some tunes on your smartphone.
What is the flight distance from Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan Intl.)?
Classified as a short-haul trip, just 860 miles (1,400 1) separates Chicago, IL (MDW-Midway Intl.) and Boston, MA (BOS-Logan Intl.). Enjoy the trip, but don’t get too settled! You’ll be touching down in Boston soon enough.
What is the earliest departure time out of Chicago to Boston?
The earliest flight departs MDW at 5:40AM and touches down at BOS at 7:55AM. Don’t forget to give yourself adequate time in the morning to get to the check-in counter.
What is the latest departure time out of Chicago to Boston?
The latest flight leaves the tarmac at MDW at 8:30PM and comes in at BOS at 10:45PM. You’ll have lots of time to prepare for this flight.
What is the average price from Chicago to Boston?
You can find a return airfare from MDW to BOS starting from around $111. The best deals sell out early, so book as soon as you know your travel dates. This price was available on Flights.com within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Chicago to Boston Flights

Whether it’s for an obligation or the sake of your sanity, sometimes you need to get away. Maybe you need flights from Chicago to Boston to attend your cousin’s wedding, to pitch a business idea to your boss, or simply treat yourself to a mini vacation. Regardless of the reasons behind packing your bags and needing to find our cheapest flights from MDW to BOS, we’ve got you covered here at Flights.com.

We present you with some of the most affordable deals on airfare, so stop that Google flights search. We want you to spend less on your flight from Chicago to Boston, so you can spend more during your getaway. With Flights.com, you’ll find it simple to land airline tickets with itineraries matching your travel schedule. What’s more, we provide you with all the information you need to confidently make reservations on your family, business, or personal trip.