Cheap Flights from Boston Logan International to Chicago Midway

Compare Boston Logan International to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from Boston Logan International Airport to Chicago Midway Airport

Looking for a cheap last-minute deal or the best return flight from Boston Logan International Airport to Chicago Midway Airport? If you want to travel next month, return fares start from Rs35,171. Find the lowest prices on one-way and return tickets right here.

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

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Boston Logan International to Chicago Midway flights are currently cheapest in June.

Direct flights from Boston Logan International to Chicago Midway

Boston Logan International to Chicago Midway: Alternative routes

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

Boston to Chicago: Flight information

The things to know before you go.
Cheapest flight foundRs19,114
Cheapest month to flyJune
Average flight time2 hrs, 43 mins
Most popular airlineSouthwest Airlines
Average flights per week33

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

The best price we found for a return flight from Boston Logan International to Chicago Midway is Rs35,171. 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 43 minutes is the average flight time from Boston Logan International to Chicago Midway.
Southwest Airlines flies direct from Boston Logan International to Chicago Midway.
As of March 2026, there are 33 flights per week flying from Boston Logan International to Chicago Midway.
The cheapest month to fly from Boston Logan International to Chicago Midway is usually April.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Boston Logan International Airport to Chicago Midway Airport on Wednesday, 8 April 2026.
Yes – the average flight time is 2 hours and 43 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 Chicago Midway 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 Chicago 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 Chicago Midway.

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

  • The average time for a direct flight from Logan International Airport to Chicago Midway International Airport is 2 hours 40 minutes.

  • Chicago's timezone is UTC-5, making Chicago one hour behind Boston.

  • Flights from BOS to MDW start at 05:05 — the first with Southwest Airlines. The latest departure is at 21:50 with Southwest Airlines. In total, you can choose from 22 weekly Logan International Airport to Chicago Midway International Airport flights.

  • Your BOS to MDW flight won't wait if you're running late, so don't forget to check in on time. Arrive up to one hour in advance for domestic flights and two hours ahead when you're flying internationally.

  • Flying during a peak month such as August? Public holidays and other popular seasons can result in longer queues at check-in and security. Play it safe and arrive up to four hours before international flights and two hours before a domestic departure.

  • Southwest Airlines is your ticket to exploring Chicago (and perhaps some other exciting corners of United States!). Check out the direct flights from Logan International Airport to Chicago Midway International Airport offered by this airline.

  • The majority of travellers choose to fly with Southwest Airlines on this route.

  • Southwest Airlines is the most punctual carrier that offers BOS to MDW flights, with 74.14% of its services arriving on schedule.

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

    • Detroit Metropolitan Wayne County Airport

    • Philadelphia International Airport

    • Ronald Reagan National Airport

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

  • Rs19,114 is currently the best price for a one-way Logan International Airport to Chicago Midway International Airport flight. A return flight starts at Rs35,171. These prices can change depending on availability.

  • Get cheap tickets from BOS to MDW by booking six months ahead. According to our research, that's the sweet spot for finding the biggest deals.

  • May is the cheapest month for flights from Logan International Airport to Chicago Midway International Airport. If you want to fly at a different time of year, the 'Whole month' tool will show you the lowest airfares for each month.

  • Picking up cheap flights from BOS to MDW is easy with Price Alerts. Simply create one of these automatic alerts and we'll notify you when a new discounted fare appears.

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

Handy information about Logan International Airport (BOS)

  • BOS's address is One Harborside Drive.

  • 73.94% of flights that depart Logan International Airport arrive at their destination on schedule.

  • Central Boston to Logan International Airport is around 5 kilometres. Depending on traffic, it'll take about 10 minutes to get there if you're ride-sharing, catching a cab or driving.

  • You can expect a trip time of about 25 minutes on public transport.

  • Catching an early flight from Logan International Airport to Chicago Midway International Airport? Avoid the hassle of rushing to the airport (and sneak in some extra precious sleep) by choosing one of these hotels near BOS:

Arriving at Chicago Midway International Airport (MDW)

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • MDW is located at 5700 South Cicero.

  • Chicago Midway International Airport to central Chicago has a drive time of around 20 minutes. It's approximately 19 kilometres away.

  • It typically takes 45 minutes to get there using public transport.

When to fly to Chicago Midway International Airport (MDW)

  • July is the busiest month for flights from Logan International Airport to Chicago Midway International Airport. For smaller crowds, visit Chicago in May.

  • Before locking in your flight from Logan International Airport to Chicago Midway International Airport, consider the type of weather you like. July is the warmest month in Chicago, with the temperature ranging from 15ºC to 29ºC.

  • January sees average temperatures of between -12ºC and 3ºC. Search for cheap tickets from BOS to MDW sometime then if you like cooler conditions.

Explore more of United States

  • You've seen Chicago, now it's time to explore other corners of United States. Travel about 451 kilometres south-east to Columbus to check off its top sights. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, there's plenty to keep you busy.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another essential stop in United States. Start your sightseeing at The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

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