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Cheap Flights from Chicago (MDW) to Boston (BOS)

Compare Chicago Midway to Boston Logan International flight deals

Find the cheapest month or even day of the year to fly to Boston Logan International

Book the best Boston Logan International fare with no extra fees

Flight deals from Chicago Midway to Boston Logan International

Looking for a cheap last-minute deal or the best return flight from Chicago Midway to Boston Logan International? Find the lowest prices on one-way and return tickets right here.
Boston.$152 per passenger.Departing Fri, 7 Nov, returning Tue, 11 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 7 Nov, arriving in Boston Logan International.Inbound direct flight with Southwest Airlines departs from Boston Logan International on Tue, 11 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $152, select.
Boston.$152 per passenger.Departing Wed, 3 Dec, returning Sat, 6 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 3 Dec, arriving in Boston Logan International.Inbound direct flight with Southwest Airlines departs from Boston Logan International on Sat, 6 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $152, select.
Boston.$152 per passenger.Departing Sat, 18 Oct, returning Thu, 23 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 18 Oct, arriving in Boston Logan International.Inbound direct flight with Southwest Airlines departs from Boston Logan International on Thu, 23 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $152, select.
Boston.$152 per passenger.Departing Sat, 6 Sep, returning Thu, 11 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 6 Sep, arriving in Boston Logan International.Inbound direct flight with Southwest Airlines departs from Boston Logan International on Thu, 11 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $152, select.
Boston.$153 per passenger.Departing Tue, 20 Jan, returning Thu, 22 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 20 Jan, arriving in Boston Logan International.Inbound direct flight with Southwest Airlines departs from Boston Logan International on Thu, 22 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $153, select.
Boston.$198 per passenger.Departing Fri, 28 Nov, returning Tue, 2 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 28 Nov, arriving in Boston Logan International.Inbound direct flight with Southwest Airlines departs from Boston Logan International on Tue, 2 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $198, select.
Boston.$198 per passenger.Departing Tue, 28 Oct, returning Sat, 1 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 28 Oct, arriving in Boston Logan International.Inbound direct flight with Southwest Airlines departs from Boston Logan International on Sat, 1 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $198, select.
Boston.$257 per passenger.Departing Mon, 25 Aug, returning Sun, 31 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 25 Aug, arriving in Boston Logan International.Inbound indirect flight with Southwest Airlines, departs from Boston Logan International on Sun, 31 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $257, select.

Find the cheapest month to fly from Chicago Midway to Boston Logan International

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Boston Logan International flights are currently cheapest in September.
Aug
from $257
Sep
from $152
Oct
from $152
Nov
from $152
Dec
from $152
Jan
from $153
Feb
from $364
Mar
from $534
Apr
Find prices
May
from $667
Jun
Find prices
Jul
from $639

Direct flights from Chicago Midway to Boston Logan International

Chicago Midway to Boston Logan International: Alternative routes

Compare routes from Chicago Midway to Boston below. You may find an airport to fly into that's cheaper, faster, or easier than Boston Logan International.

Chicago to Boston: Flight information

The things to know before you go.
Cheapest flight found$152
Cheapest month to flySeptember
Average flight time2 hrs, 18 mins
Most popular airlineSouthwest Airlines
Average flights per week27

Finding cheap flights from Chicago Midway to Boston Logan International: Frequently asked questions

The best price we found for a return flight from Chicago Midway to Boston Logan International is $152. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 18 minutes is the average flight time from Chicago Midway to Boston Logan International.
Southwest Airlines flies direct from Chicago Midway to Boston Logan International.
As of August 2025, there are 27 flights per week flying from Chicago Midway to Boston Logan International.
The cheapest month to fly from Chicago Midway to Boston Logan International is usually September.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Boston Logan International Airport on Saturday, 6 September 2025.
Yes – the average flight time is 2 hours and 18 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Boston Logan International but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Boston is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Southwest Airlines offers the cheapest flight tickets to Boston Logan International.

Travelling from Chicago Midway International Airport (MDW) to Logan International Airport (BOS): what you need to know

  • Around 2 hours 15 minutes is how long you can expect to be travelling on a direct flight from Chicago Midway International Airport to Logan International Airport.

  • Boston's timezone is UTC-4, which makes Boston one hour ahead of Chicago.

  • Each week, there are 22 Chicago Midway International Airport to Logan International Airport flights. If you prefer to get going as early as possible, jump on the 05:00 Southwest Airlines flight. If you'd rather make the most of your day before flying, the last departure is at 21:15 with Southwest Airlines.

  • To ensure you get on your MDW to BOS flight, allow plenty of time to check in and drop off your luggage. Arriving two hours ahead of international departures and one hour before domestic flights is the general rule.

  • Flying during a peak month like July? Major public holidays and other popular periods can mean longer lines and delays at check-in and security. Play things extra safe and get there up to four hours before an international flight and two hours before domestic departures.

  • Southwest Airlines is your gateway to exploring Boston (and perhaps some other exciting parts of United States!). Browse the direct flights from Chicago Midway International Airport to Logan International Airport offered by this popular airline.

  • The majority of passengers choose to travel with Southwest Airlines on this route.

  • Southwest Airlines is the most punctual carrier that offers MDW to BOS flights, with 72.99% of its services arriving on schedule.

  • Consider adding a stopover when booking your ticket from Chicago Midway International Airport to Logan International Airport. Just uncheck 'Direct flights only' to break up your trip, or enjoy a detour to a new and interesting place. Here's where you can stop between MDW and BOS:

    • John Glenn Columbus International Airport

    • Detroit Metropolitan Wayne County Airport

    • Philadelphia International Airport

How to find the cheapest flights from Chicago Midway International Airport (MDW) to Logan International Airport (BOS)

  • The cheapest price we've found for a one-way Chicago Midway International Airport to Logan International Airport flight is $76. A return fare right now is $152. Depending on the availability when you book, these fares may change.

  • Book six months before you travel. After looking at the numbers on our calendar, this is how far you should book ahead to find cheap tickets from MDW to BOS.

  • Plan your trip for May. That's the cheapest month for flights from Chicago Midway International Airport to Logan International Airport. If your travel dates are flexible, use the 'Whole month' tool to see the lowest airfare across each month.

  • Cut down on the time spent looking for cheap flights from MDW to BOS by creating a Price Alert. You'll get an email or notification through the app when fares go down.

  • Choose your ideal departure and arrival times, airlines and number of stops with the filters. Alternatively, sort your results by 'Cheapest' to get the best deals on flights from Chicago Midway International Airport to Logan International Airport.

Handy information about Chicago Midway International Airport (MDW)

  • MDW is located at 5700 South Cicero.

  • When it comes to Chicago Midway International Airport's on-time performance, data shows 77.88% of flights meet their scheduled arrival time.

  • To get to Chicago Midway International Airport from central Chicago, it'll take around 20 minutes if you're travelling by car. This depends on traffic, however. It's approximately 19 kilometres from the airport to the city centre.

  • Catching public transport? Expect a trip time of around 45 minutes.

  • Get your travels off to a hassle-free start by staying near MDW. Whether you're boarding an early flight from Chicago Midway International Airport to Logan International Airport or just don't want to be rushed, these hotels have you covered:

Arriving at Logan International Airport (BOS)

Getting from Logan International Airport (BOS) to central Boston

  • The street address for BOS is One Harborside Drive.

  • Logan International Airport is approximately 5 kilometres from central Boston. The drive time takes around 10 minutes.

  • Getting to the centre on public transport will take you roughly 25 minutes.

When to fly to Logan International Airport (BOS)

  • It's time to pick your trip dates for your flight from Chicago Midway International Airport to Logan International Airport. August is the busiest month to visit Boston. If you like a more laid-back vibe, go in May.

  • Before locking in your flight from Chicago Midway International Airport to Logan International Airport, think about the kind of weather you enjoy. July is the warmest month in Boston, with temperatures ranging from 16ºC (61ºF) to 29ºC (84ºF).

  • If you want cooler conditions, look for a cheap ticket from MDW to BOS in January. Temperatures average between -8ºC (18ºF) and 6ºC (43ºF) then.

Explore more of United States

  • New York is just one of the many places in United States waiting to be explored after you've experienced Boston. Around 306 kilometres away to the south-west, its top attractions include Statue of Liberty, Central Park and Empire State Building.

  • If you're interested in discovering another great destination in United States, consider Philadelphia, roughly 434 kilometres south-west of Boston. Liberty Bell, Independence Hall and Philadelphia Museum of Art are key reasons to visit.

Plan the rest of your trip from Chicago to Boston

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.