Flights from Logan Intl. (BOS) to Midway Intl. (MDW) starting at $68

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Find The Best Dates To Fly from Logan Intl. to Midway Intl.

Amazing BOS to MDW Flight Deals

The cheapest flights to Midway Intl. found within the past 7 days were $116 round trip and $68 one way. Prices and availability subject to change. Additional terms may apply.

Best Midway Intl. Flight and Hotel Packages

Midway Intl. flight + hotel packages - economy flights

Swissotel - Chicago
Fairmont Chicago at Millennium Park Gold Experience
Fairmont Chicago at Millennium Park
The Langham, Chicago
Hotel Lincoln, part of JdV by Hyatt
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FAQs about flights from Logan Intl. Airport (BOS) to Midway Intl. Airport (MDW)

Can I catch a flight from Boston, MA Airport (BOS-Logan Intl.) to Chicago, IL Airport (MDW-Midway Intl.) right now?

Ensure you go to our Covid-19 Travel Advisor to learn if there are any current travel advice reports and quarantine requirements in place in Chicago, IL Airport (MDW-Midway Intl.) when flying in from Boston, MA Airport (BOS-Logan Intl.).

Are there direct flights from Logan Intl. Airport to MDW?

You'll have trouble finding a flight direct from BOS to Chicago, IL Airport (MDW-Midway Intl.), but don't stress. Delta, Aeromexico and Virgin Atlantic provide flights with only one stopover.

If I am not able to travel due to COVID-19, can I change my booking to a later date?

For more info about changing your flight to MDW, please visit our Customer Service Portal.

How long is the flight from Logan Intl. Airport to Chicago Airport?

The flight from Boston to Chicago takes just 2 hours and 39 minutes in total. With such a short travel time, you won't need to fret if you forget to pack your phone charger in your carry-on bag.

What is the flight distance from Logan Intl. Airport to Midway Airport?

Traveling 1,429 mi between Logan Intl. Airport and Logan Intl. Airport calls for a glass of vino and some quality screen time. Put your seat back, get cozy and simply enjoy the flight.

What airlines fly from Logan Intl. Airport to Chicago, IL Airport (MDW-Midway Intl.)?

No direct flights are between Logan Intl. Airport (BOS) and Chicago, IL Airport (MDW-Midway Intl.). Start planning early to save time and find the easiest route with minimal stopovers.

What airlines have practices regarding COVID-19 in place and use social distancing?

From the moment you enter the departure terminal to when you leave the arrivals terminal, if you're flying with Southwest Airlines, Delta or Volaris you can be sure that COVID-19 measures and social distancing rules have been adhered to. Many airlines have introduced capped capacity flights and keeping the middle seat empty.

What is the best day to buy a plane ticket?

This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2020. Wednesday and Friday prices are also good, but you may want to prepare your budget if booking on a Sunday, as data shows the end of the week is when prices are generally at their highest.

What are the cheapest days to fly?

Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2020, flights departing on a Monday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.

How far in advance can you book a flight?

Trying to figure out how early you should book your flight? It's possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2020 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2 weeks to 2 months prior to their travel dates.

How can I save money on airline tickets?

We'll let you in on a secret...You can save big on flights if you mix and match your airlines and fare types. In fact, travelers who booked flights on Travelocity in 2020 saved nearly 40% when their return flights consisted of two different airlines or fare types.

*According to flight demand on from January to December 2020. Savings are subject to change based on departure location, date and destination.

Logan Intl. to Midway Intl. Flight FAQ

Traveling From Logan Intl.
Traveling To Midway Intl.
Shortest Flight Time 0 hours 45 mins
Earliest Departure Time 6:30AM CDT
Latest Departure Time 5:55PM CDT
Lowest Flight Price $116

Route Info

Flight path for flights from Logan International Airport to Chicago Midway International Airport.

863.00 miles

Discover our best flights from Boston BOS to Chicago MDW. 

With 19 airlines to choose from on Travelocity, you can easily find the best option for you. Use our filters to sort by price, compare airlines, and find the most convenient flight times. 


Find our best return flights from Boston BOS to Chicago MDW at the right price  

Airfares to Chicago MDW from Boston BOS currently cost between $116 and $151. It’s usually cheaper to book a round trip than two separate one-way flights. Prices and availability subject to change. Additional terms may apply. 


Book one-way flights from Boston BOS to Chicago MDW 

If you want to be flexible about when you return, or keep your travel options open ended, a one-way flight could be just the ticket! You’ll find one-way airfares from Boston BOS to Chicago MDW on Travelocity starting at $68. Prices and availability subject to change. Additional terms may apply. 


Get to Chicago MDW from Boston BOS quicker with direct flights. 

Get to Chicago faster, without the hassle of changing planes and moving baggage, by booking a direct flight. Expect your direct flight to MDW from BOS to take around 0 hour(s) 45 min(s).  


Find our cheapest airfares for flights from Boston BOS to Chicago MDW

Find cheap flight deals by using our search filters to sort results starting with the lowest price airfares to MDW from BOS. Our Price Match Promise means if you find a lower rate on or on another US-based website within 24 hours of booking, we’ll credit or refund the difference.  


Get our best airfare deals for your flight from Boston BOS to Chicago MDW today 

If you’re flexible about when you travel, October is usually the cheapest month to fly from Boston BOS to Chicago MDW. If you need to be more specific, search by date and arrival and departure times.Then, compare prices across different airlines, and sort results by lowest price first. 


Book flexible airline tickets for flights to Chicago MDW from Boston BOS 

Some airlines let you change your travel dates without charging a fee. Use our ‘no change fee’ filter to see which flights to MDW from BOS have this option.  


Travel with confidence when you book flights to Chicago MDW from Boston BOS with Travelocity 

We’ve secured fantastic deals with all the main airline carriers and it’s easy to compare, choose, and book with Travelocity. With 24/7 customer service and our free 'App', we’ll always keep you moving. 

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.