BOS to MDW (Boston to Chicago) Flights

Last Minute Flights from BOS to MDW

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

OriginDestinationTravel DatesFlights From*
BOSChicagoMarch 22 to March 28$237
*Prices include taxes and fees

Cheapest BOS to MDW Flights

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

OriginDestinationTravel DatesFlights From*
BOSChicagoMay 6 to May 8$157
BOSChicagoMay 6 to May 8$167
BOSChicagoMarch 31 to April 4$169
BOSChicagoMay 6 to May 8$335
*Prices include taxes and fees
BOS to MDW Flight Details
Origin airport
Logan Intl.
Origin airport IATA code
BOS
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Distance
857 mi

Frequently asked questions

What airlines fly direct from Logan Intl. Airport to Chicago Airport?
No airlines fly straight from Logan Intl. Airport (BOS) to Midway Airport. To get to Chicago, you'll have to book a flight with at least one stop.
How many flights are there from BOS to MDW?
Approximately 3 services operate per day between Boston, MA (BOS-Logan Intl.) and Chicago, IL (MDW-Midway Intl.). Fasten your safety belt because your plane to Chicago is ready to leave.
How long does it take to fly from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.)?
From Boston, MA (BOS-Logan Intl.), it's only 2 hours and 37 minutes to Chicago, IL (MDW-Midway Intl.). Don't get too relaxed in your seat — you'll be landing in Chicago in a flash.
What is the flight distance from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.)?
It's a mere 860 miles (1,400 1) from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.), making it a short-haul flight. Book a window seat and be dazzled by the landscapes of Chicago as you prepare to land.
What is the earliest departure time out of Boston to Chicago?
Leave BOS at 6:40AM and arrive at MDW at 9:15AM. This is the earliest flight available on this route.
What is the latest departure time out of Boston to Chicago?
The latest flight jets out from BOS at 9:55PM and arrives at MDW at 12:30AM. You'll have more than enough time to get ready for this journey.
What is the average price from Boston to Chicago?
Flights from BOS to MDW can be found for around $157. You'll want to move fast, because fares this good always go quickly! 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.

Boston to Chicago Flights

Whether it’s for an obligation or the sake of your sanity, sometimes you need to get away. Maybe you need flights from Boston to Chicago 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 BOS to MDW, 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 Boston to Chicago, 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.

Plan Your Trip