Popular airlines from Logan International Airport (BOS) to Chicago Midway Airport (MDW)
Southwest AirlinesSouthwest Airlines
DeltaDelta
Frontier AirlinesFrontier Airlines
Today's featured flight deals from Logan International Airport (BOS) to Chicago Midway Airport (MDW)
- Boston (BOS) to Chicago (MDW).Southwest Airlines, nonstop.Departing on Fri, Sep 12 at 5:15am from Boston, arriving at 6:45am in Chicago.Returning on Mon, Sep 15 at 6:45pm from Chicago, arriving at 10:05pm in Boston.Select Southwest Airlines flight departing on Fri, Sep 12 at 5:15am from Boston, returning on Mon, Sep 15 at 6:45pm from Chicago priced at $15760% less than typical$157
- Boston (BOS) to Chicago (MDW).Southwest Airlines, nonstop.Departing on Sun, Sep 21 at 5:30am from Boston, arriving at 7:05am in Chicago.Returning on Wed, Sep 24 at 6:25am from Chicago, arriving at 12:15pm in Boston.Select Southwest Airlines flight departing on Sun, Sep 21 at 5:30am from Boston, returning on Wed, Sep 24 at 6:25am from Chicago priced at $21750% less than typical$217
- Boston (BOS) to Chicago (MDW).Southwest Airlines, nonstop.Departing on Thu, Sep 18 at 5:15am from Boston, arriving at 6:45am in Chicago.Returning on Sun, Sep 21 at 5:55am from Chicago, arriving at 9:10am in Boston.Select Southwest Airlines flight departing on Thu, Sep 18 at 5:15am from Boston, returning on Sun, Sep 21 at 5:55am from Chicago priced at $15755% less than typical$157
- Boston (BOS) to Chicago (MDW).Southwest Airlines, nonstop.Departing on Sat, Sep 13 at 5:50am from Boston, arriving at 7:25am in Chicago.Returning on Mon, Sep 22 at 6:45pm from Chicago, arriving at 10:05pm in Boston.Select Southwest Airlines flight departing on Sat, Sep 13 at 5:50am from Boston, returning on Mon, Sep 22 at 6:45pm from Chicago priced at $15755% less than typical$157
- Boston (BOS) to Chicago (MDW).Southwest Airlines, nonstop.Departing on Thu, Sep 18 at 5:15am from Boston, arriving at 6:45am in Chicago.Returning on Mon, Sep 22 at 6:45am from Chicago, arriving at 10:00am in Boston.Select Southwest Airlines flight departing on Thu, Sep 18 at 5:15am from Boston, returning on Mon, Sep 22 at 6:45am from Chicago priced at $15755% less than typical$157
- Boston (BOS) to Chicago (MDW).Southwest Airlines, nonstop.Departing on Thu, Oct 2 at 5:15am from Boston, arriving at 6:55am in Chicago.Returning on Sun, Oct 5 at 6:05am from Chicago, arriving at 9:20am in Boston.Select Southwest Airlines flight departing on Thu, Oct 2 at 5:15am from Boston, returning on Sun, Oct 5 at 6:05am from Chicago priced at $15750% less than typical$157
- Boston (BOS) to Chicago (MDW).Southwest Airlines, nonstop.Departing on Sun, Sep 21 at 5:30am from Boston, arriving at 7:05am in Chicago.Returning on Sat, Sep 27 at 5:40pm from Chicago, arriving at 9:00pm in Boston.Select Southwest Airlines flight departing on Sun, Sep 21 at 5:30am from Boston, returning on Sat, Sep 27 at 5:40pm from Chicago priced at $19740% less than typical$197
- Boston (BOS) to Chicago (MDW).Southwest Airlines, nonstop.Departing on Sat, Sep 6 at 4:55pm from Boston, arriving at 6:35pm in Chicago.Returning on Sat, Sep 13 at 9:51am from Chicago, arriving at 1:20pm in Boston.Select Southwest Airlines flight departing on Sat, Sep 6 at 4:55pm from Boston, returning on Sat, Sep 13 at 9:51am from Chicago priced at $26730% less than typical$267
- Boston (BOS) to Chicago (MDW).Southwest Airlines, nonstop.Departing on Wed, Oct 8 at 5:15am from Boston, arriving at 6:55am in Chicago.Returning on Sat, Oct 11 at 6:30am from Chicago, arriving at 9:45am in Boston.Select Southwest Airlines flight departing on Wed, Oct 8 at 5:15am from Boston, returning on Sat, Oct 11 at 6:30am from Chicago priced at $19735% less than typical$197
Cheap Flights from Boston to Chicago (BOS-MDW)
Prices were available within the past 7 days and start at $77 for one-way flights and $154 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
Graph displaying average flight prices per month
Alternative airports near Chicago
Prices were available within the past 7 days. Prices and availability are subject to change.
Origin airport | Logan Intl. |
Destination airport | Midway Intl. |
Airlines serving | Delta, Frontier Airlines, Southwest Airlines |
Roundtrip price | $154 |
Distance | 857 mi |
Average flight time | 1 hour 38 mins |
Boston to Chicago Flights
The cheapest times to fly from Boston to Chicago
On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Boston to Chicago are during the month of October. You can find some of the cheapest flights from Boston to Chicago with Expedia's search tool and vast selection of airlines.
The best time to book a flight from Boston to Chicago
Sunday is one of the best days to book for cheap flights from Boston to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.
How to find cheap round-trip tickets from Boston to Chicago
Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Boston to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $77 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.
Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Boston to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.
You could also save big by booking one of Expedia's vacation packages. Bundling together your Boston to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.
*Terms apply.
Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.
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