CA $210 Cheap Flights from Boston (BOS) to Chicago (MDW)

Featured airlines

    Plan, book, fly with confidence
  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • payments icon
    Earn twice
    Earn your airline miles on top of our rewards

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

Prices were available within the past 7 days and start at CA $210 for one-way flights and CA $429 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Delta
Delta
Delta
Delta
Delta
Delta
Delta
Delta
Delta
Flight from Boston to Chicago (BOS - MDW) route information
Origin airport
Logan Intl.
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
CA $429
Distance
1371 km
Average flight time
1 hour 45 mins

Boston to Chicago Flights

The easy way to book your flights from Boston to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from Boston whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are Southwest Airlines nonstop flights to Midway Intl., too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Boston to Chicago today, tomorrow, or this week.  

 

Save dollars with cheap flights from Logan Intl., BOS to Midway Intl., MDW 

Sort your search results by price to find great deals on your flight from Boston to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Boston currently is just CA $429 rising to CA $609.  

Here are more money-saving tips: 

  • Fly in April when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Chicago  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Chicago from Boston 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today.

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 CA $429. 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 canceled 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 kilometers 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.
Chicago nearby Airports

Chicago

Boston nearby Airports

Providence

*Available to Expedia members.