MDW to BOS (Chicago to Boston) Flights

Last Minute Flights from MDW to BOS

Best airfare and ticket deals for MDW to BOS flights are based on recent deals found by Expedia.com customers within the past 7 days.

OriginDestinationTravel DatesFlights From*
MDWBostonApril 28 to May 11$131
*Prices include taxes and fees

Cheapest MDW to BOS Flights

Best airfare and ticket deals for MDW to BOS flights are based on recent deals found by Expedia.com customers within the past 7 days.

OriginDestinationTravel DatesFlights From*
MDWBostonMay 4 to May 8$96
MDWBostonMay 11 to May 15$106
MDWBostonMay 4 to May 11$107
MDWBostonMay 7 to May 14$246
*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

Which airlines with flights from Midway International Airport to BOS allow free cancellation due to COVID-19?
Quite a few airlines now advertise airfares with more flexibility so you can organize your journey to BOS with confidence. To figure out which carriers have these kinds of tickets, use our convenient filter tool. Just click the “No change fee” check box directly under the “Flexible change policies” section. Also read the ticket’s terms and conditions so you’re familiar with what COVID-19 related changes are covered.
What airlines fly direct from Chicago, IL Airport (MDW-Midway Intl.) to BOS?
If you’re eager to fly straight from Chicago, IL Airport (MDW-Midway Intl.) to Boston, MA Airport (BOS-Logan Intl.), Southwest Airlines (WN) is a top choice. It advertises 91 flights each month between these destinations.
How many flights are there from MDW to BOS?
Approximately 33 per day. If you’re in a hurry to get to Boston, see if you can grab a fabulous last-minute deal from Chicago, IL Airport (MDW-Midway Intl.) to Boston, MA Airport (BOS-Logan Intl.) and then reserve it right away!
How long does it take to fly from Chicago, IL Airport (MDW-Midway Intl.) to Boston, MA Airport (BOS-Logan Intl.)?
While you won’t be squished in your seat for too long from Chicago, IL Airport (MDW-Midway Intl.) to Boston, MA Airport (BOS-Logan Intl.), 4 hours and 8 minutes isn’t exactly a short ride either. Consider upgrading your ticket if you’re after more leg space.
What is the flight distance from Chicago, IL Airport (MDW-Midway Intl.) to Boston, MA Airport (BOS-Logan Intl.)?
Chicago, IL Airport (MDW-Midway Intl.) to Boston, MA Airport (BOS-Logan Intl.) is a short-haul trip of 860 miles (1400 km). You’ll hardly have time to relax in your seat before your plane hits the tarmac in Boston.
How many morning flights are there from MDW to BOS?
With 108 morning flights from MDW to BOS a week, you have lots of choice.
  • Pack your suitcase and jet off with Southwest Airlines (WN). It operates 66 flights weekly that depart before midday. The first one takes off at 5:35AM.
  • As another option, lock in a ticket with Delta (DL) and fly out as early as 6:01AM. This company offers 35 morning flights every week between MDW and BOS.
How many afternoon flights are there from MDW to BOS?
Every week, you can decide between 125 afternoon and evening flights from MDW to BOS.
  • Jet off with Southwest Airlines (WN), which lists 80 afternoon and evening flights every week on this route. The earliest scheduled departure is 12:00PM.
  • Delta (DL) is a good alternative, offering 37 afternoon and evening flights each week. The earliest leaves the runway at 12:40PM.
What is the earliest departure time out of Chicago to Boston?
The earliest flight jets off from MDW at 5:35AM and lands at BOS at 11:20PM. Don’t forget to give yourself plenty of time in the morning to get to your departure gate.
What is the latest departure time out of Chicago to Boston?
Secure a seat on the 9:55PM flight from MDW, arriving at 3:10PM at BOS, and give yourself time to attend to those last-minute vacation preparations. This is the latest flight you can get on this route.
What is the average price from Chicago to Boston?
Round-trip journeys for this route start from around $96. When you’re ready to take to the skies, we’ll help you land the best deal in town. 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 perhaps simply to treat yourself to a mini vacation. Regardless of the reasons behind packing your bags and needing to find the cheapest flights from MDW to BOS, we’ve got you covered here at Flights.com.

We present you with some of the hottest 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.