฿5,160 Cheap Flights from Boston (BOS) to Chicago (MDW)

View ฿5,160 flight on Wed, 10 Sep 2025Opens in a new window

Popular airlines from Logan International Airport (BOS) to Chicago Midway Airport (MDW)

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

Prices were available within the past 7 days and start at ฿5,160 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Find the cheapest month to fly from Boston (BOS) to Chicago (MDW)

September is typically the cheapest month to fly

From ฿2,478 - ฿11,436 per traveller.

Graph displaying average flight prices per month

Flight from Boston to Chicago route information
Origin airport
Logan Intl.
Destination airport
Midway Intl.
Distance
1371 km
Average flight time
1 hour 37 mins

Perfect flights from Boston to Chicago

Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Boston to Chicago. Whether you're aching for a romantic escape with your partner, craving an adventurous solo expedition, or yearning to immerse yourself in the local history and culture, we've got you covered.
 
Picture yourself strolling through the streets of , surrounded by breathtaking architecture and absorbing the vibrant atmosphere of this captivating city. Indulge in the mouth-watering local specialties, from tantalizing street food to exquisite fine dining. With Expedia, you can experience all of this and more, without sacrificing your budget.
 
Our flexible Logan Intl. to Midway Intl. ticket options cater to your travel preferences, with incredible one-way fares from ฿5,160 and roundtrip prices . Whether you're planning a short city break or a longer adventure, our dynamic pricing ensures that you find the best deals for your journey.
 
But the magic doesn't stop there. Expedia offers a range of partner services to enhance your trip. Rent a car at Midway Intl. and explore and its surrounding areas at your own pace. Discover hidden gems off the beaten path, and create unforgettable memories. We also provide a handpicked selection of accommodations, from charming bed and breakfasts to luxury hotels, ensuring that you have a comfortable and memorable stay.
 
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support are designed to make your travel experience seamless and stress-free. So, why wait? Book your to travel arrangements today and embark on the journey of a lifetime in Chicago.

Frequently asked questions

How much is a flight from Logan Intl. Airport to Midway Intl. Airport (MDW)?
Based on fares advertised within the last 7 days on Expedia for flights departing within the next year, round-trip journeys from Logan Intl. Airport (BOS) to MDW start from . Make your booking today to score the best price for your journey. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Logan Intl. Airport to MDW?
The majority of flights can be cancelled online, but whether you are charged a fee depends on your airline. If you do need to cancel your getaway, follow the easy instructions in the Customer Service Portal.
How do I find cheap flights from Logan Intl. Airport (BOS) to Chicago Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for BOS to Midway Intl. Airport (MDW) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Logan Intl. Airport (BOS) to Chicago Airport?
You can forget about a movie marathon on this flight — it's only 1,400 kilometres from Boston to Chicago. Find your seat, get comfortable and you'll be there before you know it.
Which airlines fly direct from Logan Intl. Airport to Chicago Airport?
If you're looking to fly directly from Logan Intl. Airport to MDW, Southwest Airlines (WN) is an excellent choice. It operates 121 flights every month between Boston and Chicago.
Are Logan Intl. Airport (BOS) to MDW flight tickets cheaper when they're purchased at the last minute?
Late planners can sometimes pick up a bargain, with some super cheap airfares from Logan Intl. Airport (BOS) to Midway Intl. Airport (MDW) showing up a few weeks prior to the departure date. If you'd rather plan ahead, Expedia compares and updates all the best flight deals continually — as early as a year in advance in some cases. It does depend on the carrier though, as not all airlines advertise prices that far in advance.

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Chicago Airports

Chicago

Boston to O'Hare Intl.
฿4,470.00
*Available to Expedia members.