$59 Cheap Flights from Boston (BOS) to Chicago (MDW)

View $59 flight on Wed, Nov 12, 2025Opens in a new window

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

Today's featured flight deals from Logan International Airport (BOS) to Chicago Midway Airport (MDW)

Nonstop
Carry-on included
Lower price than typical

Cheap Flights from Boston to Chicago (BOS-MDW)

Prices were available within the past 7 days and start at $59 for one-way flights and $117 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Fri, Oct 31 - Sat, Nov 1
BOS
Boston
MDW
Chicago
$117 Roundtrip, just found
$117
Roundtrip
just found
Select Southwest Airlines flight, departing Fri, Oct 31 from Boston to Chicago, returning Sat, Nov 1, priced at $117 just found
Frontier Airlines
Thu, Dec 4 - Thu, Dec 11
BOS
Boston
MDW
Chicago
$118 Roundtrip, found 6 days ago
$118
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Dec 4 from Boston to Chicago, returning Thu, Dec 11, priced at $118 found 6 days ago
Southwest Airlines
Fri, Oct 31 - Sat, Nov 1
BOS
Boston
MDW
Chicago
$127 Roundtrip, just found
$127
Roundtrip
just found
Select Southwest Airlines flight, departing Fri, Oct 31 from Boston to Chicago, returning Sat, Nov 1, priced at $127 just found
Southwest Airlines
Fri, Oct 31 - Sat, Nov 1
BOS
Boston
MDW
Chicago
$132 Roundtrip, just found
$132
Roundtrip
just found
Select Southwest Airlines flight, departing Fri, Oct 31 from Boston to Chicago, returning Sat, Nov 1, priced at $132 just found
Southwest Airlines
Tue, Nov 4 - Fri, Nov 7
BOS
Boston
MDW
Chicago
$137 Roundtrip, just found
$137
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Nov 4 from Boston to Chicago, returning Fri, Nov 7, priced at $137 just found
Southwest Airlines
Mon, Dec 29 - Tue, Dec 30
BOS
Boston
MDW
Chicago
$137 Roundtrip, found 19 hours ago
$137
Roundtrip
found 19 hours ago
Select Southwest Airlines flight, departing Mon, Dec 29 from Boston to Chicago, returning Tue, Dec 30, priced at $137 found 19 hours ago
Southwest Airlines
Fri, Oct 31 - Sat, Nov 1
BOS
Boston
MDW
Chicago
$142 Roundtrip, just found
$142
Roundtrip
just found
Select Southwest Airlines flight, departing Fri, Oct 31 from Boston to Chicago, returning Sat, Nov 1, priced at $142 just found
Southwest Airlines
Fri, Nov 14 - Sun, Nov 16
BOS
Boston
MDW
Chicago
$153 Roundtrip, found 15 hours ago
$153
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Fri, Nov 14 from Boston to Chicago, returning Sun, Nov 16, priced at $153 found 15 hours ago
Frontier Airlines
Thu, Nov 6 - Fri, Nov 7
BOS
Boston
MDW
Chicago
$154 Roundtrip, found 14 hours ago
$154
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Thu, Nov 6 from Boston to Chicago, returning Fri, Nov 7, priced at $154 found 14 hours ago
Delta
Wed, Nov 5 - Mon, Nov 10
BOS
Boston
MDW
Chicago
$283 Roundtrip, found 2 hours ago
$283
Roundtrip
found 2 hours ago
Select Delta flight, departing Wed, Nov 5 from Boston to Chicago, returning Mon, Nov 10, priced at $283 found 2 hours ago

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

September is typically the cheapest month to fly

From $76 - $299 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Average driving time to city center is 23 minutes. Flights from $225
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $225

Frequently asked questions

How much does a flight from Logan Intl. Airport (BOS) to Midway Intl. Airport (MDW) cost?
Grab a cheap one-way flight from $59 or cheap return flight from $117 from Logan Intl. Airport (BOS) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Logan Intl. Airport (BOS) to Midway Intl. Airport (MDW)?
Traveling in October can help you save, as it's the cheapest month for flights between BOS and MDW. You'll often find the lowest prices during the off-season.
Which airlines fly direct from Logan Intl. Airport (BOS) to Midway Intl. Airport (MDW)?
If you're departing from Logan Intl. Airport (BOS), you can catch a direct flight to Midway Intl. Airport (MDW) with Southwest Airlines.
What is the cheapest airline that flies from Logan Intl. Airport (BOS) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare different airlines, departure times and fares all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to find the carrier with the cheapest BOS to MDW flight.
How many flights per day from Logan Intl. Airport (BOS) to Midway Intl. Airport (MDW)?
With an average of 2 direct flights departing from Logan Intl. Airport (BOS) to Midway Intl. Airport (MDW) each day, you'll be cruising above the clouds before you know it.
What are the most popular departure times for flights from Logan Intl. Airport (BOS) to Midway Intl. Airport (MDW)?
More passengers fly between BOS and MDW at 7 AM than at any other time of day. Rather go when it's quieter? Pick a flight outside the busiest times and you could save on your ticket as well.
What day of the week has the most flights from BOS to MDW?
Fly on a Saturday if you're looking for the largest selection of flights from Logan Intl. Airport (BOS) to Midway Intl. Airport (MDW).
What is the earliest flight from Logan Intl. Airport (BOS) to Midway Intl. Airport (MDW)?
Catch the earliest flight at around 5:50AM UTC-5, heading out of Logan Intl. Airport (BOS). You'll be flying for roughly 3h, touching down at Midway Intl. Airport (MDW) at approximately 7:50AM UTC-6.
How long does it take to fly from Logan Intl. Airport (BOS) to Midway Intl. Airport (MDW)?
Flights from BOS to MDW have an average travel time of 2 hours and 52 minutes. The total distance between the two airports is 860 mi.
What airline has the least delays from BOS to MDW?
United Airlines has the best performance for on-time direct flights from Logan Intl. Airport (BOS) to Midway Intl. Airport (MDW), with an on-time rating of 100%. Use the Expedia App to view your journey status before you go and get notified of any changes.
What is the best time to fly from Logan Intl. Airport (BOS) to Midway Intl. Airport (MDW)?
To arrive at Midway Intl. Airport (MDW) without delays, select a flight that leaves Logan Intl. Airport (BOS) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Logan Intl. Airport (BOS)?
Board a direct flight from Logan Intl. Airport (BOS) to Chicago and arrive at O'Hare Intl. Airport (ORD). Another arrival point to this destination is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Logan Intl. Airport (BOS) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from BOS to MDW right before your getaway is typically more expensive. But if there's some wiggle room with your departure dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a BOS to MDW flight and hotel package?
Compared with arranging hotels and flights separately, booking a BOS to MDW flight and hotel package with Expedia could lead to significant savings. Better still, having everything in one convenient place will take the stress out of travel planning. Just pick your flights and select from our extensive range of hotels, then tailor your trip with other add-ons like tours, activities and car rentals.
Can I cancel or change the date of my flight from Logan Intl. Airport (BOS) to Midway Intl. Airport (MDW)?
Typically, it's possible to reschedule or cancel your BOS to MDW flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find more details on our Customer Service portal.

Travel information

Origin airport
Logan Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$117
Distance
857 mi
Average flight time
1 hour 42 mins

Book with confidence

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 $59 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.

 

Boston to Chicago Flights

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*Available to One Key members.