$55 Cheap flights from Logan Intl. to Midway Intl. (BOS to MDW)

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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 $110 round trip and $55 one way. Prices and availability subject to change. Additional terms may apply.

Wed, Dec 11 - Wed, Dec 11
BOS
Boston
MDW
Chicago
$110 Roundtrip, found 1 day ago
$110
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Dec 11 from Boston to Chicago, returning Wed, Dec 11, priced at $110 found 1 day ago
Wed, Dec 11 - Tue, Dec 17
BOS
Boston
MDW
Chicago
$113 Roundtrip, found 1 day ago
$113
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Dec 11 from Boston to Chicago, returning Tue, Dec 17, priced at $113 found 1 day ago
Wed, Dec 11 - Mon, Dec 16
BOS
Boston
MDW
Chicago
$114 Roundtrip, found 1 day ago
$114
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Dec 11 from Boston to Chicago, returning Mon, Dec 16, priced at $114 found 1 day ago
Wed, Dec 11 - Tue, Dec 17
BOS
Boston
MDW
Chicago
$115 Roundtrip, found 6 hours ago
$115
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Wed, Dec 11 from Boston to Chicago, returning Tue, Dec 17, priced at $115 found 6 hours ago
Wed, Jan 15 - Tue, Jan 28
BOS
Boston
MDW
Chicago
$116 Roundtrip, found 7 hours ago
$116
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Wed, Jan 15 from Boston to Chicago, returning Tue, Jan 28, priced at $116 found 7 hours ago
Mon, Jan 27 - Tue, Feb 4
BOS
Boston
MDW
Chicago
$117 Roundtrip, found 11 hours ago
$117
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Mon, Jan 27 from Boston to Chicago, returning Tue, Feb 4, priced at $117 found 11 hours ago
Wed, Dec 11 - Mon, Dec 16
BOS
Boston
MDW
Chicago
$118 Roundtrip, found 8 hours ago
$118
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Wed, Dec 11 from Boston to Chicago, returning Mon, Dec 16, priced at $118 found 8 hours ago
Fri, Dec 6 - Wed, Dec 11
BOS
Boston
MDW
Chicago
$124 Roundtrip, found 1 day ago
$124
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Dec 6 from Boston to Chicago, returning Wed, Dec 11, priced at $124 found 1 day ago
Fri, Dec 6 - Tue, Dec 10
BOS
Boston
MDW
Chicago
$125 Roundtrip, found 1 hour ago
$125
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Dec 6 from Boston to Chicago, returning Tue, Dec 10, priced at $125 found 1 hour ago
Fri, Jan 31 - Tue, Feb 4
BOS
Boston
MDW
Chicago
$127 Roundtrip, found 11 hours ago
$127
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Fri, Jan 31 from Boston to Chicago, returning Tue, Feb 4, priced at $127 found 11 hours ago

Best Midway Intl. Flight and Hotel Packages

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
per person
Jan 3 - Jan 9
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Save 100% on your flight
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
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Frequently asked questions

Can I catch a flight from BOS to Chicago Airport right now?
Be sure to visit the Covid-19 Travel Advisor to find out if there are any present travel advice reports and quarantine requirements in place in Midway Intl. Airport (MDW) when jet-setting from Logan Intl. Airport (BOS).
Are there direct flights from Logan Intl. Airport (BOS) to Chicago Airport?
If you’re not a big fan of stopovers, you’ll want to organize your flight from Logan Intl. Airport to Midway Intl. Airport (MDW) ahead of time. Southwest Airlines is the only air carrier that operates direct flights between Boston and Chicago.
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 Chicago Airport, please visit our Customer Service Portal.
How long is the flight from Logan Intl. Airport to MDW?
Exit the airplane feeling rested and relaxed by having a nap and some refreshments during your flight to Midway Airport. With an usual travel time of 4 hours and 34 minutes from Logan Intl. Airport (BOS), you’ll have ample time to enjoy both.
What is the flight distance from BOS to Midway Intl. Airport (MDW)?
With a flight distance of only 860 mi, a newspaper or an episode of your favorite TV show is all you’ll really need to keep yourself amused on the journey between Logan Intl. Airport and Midway Airport. You’ll be disembarking the plane and diving into your thrilling travel itinerary in no time.
What airlines fly from Logan Intl. Airport (BOS) to MDW?
With Southwest Airlines, you won’t have to put up with annoying layovers or standing around waiting to board your next flight. This popular airline will take you nonstop from Logan Intl. Airport (BOS) to Midway Airport on one of the 91 flights offered on this route every month.
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 2021. Tuesday and Wednesday prices are also good, but you may want to prepare your budget if booking during the weekend, as data shows that 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 2021, 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 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 0-2 weeks prior to their travel dates.*According to flight demand on Travelocity.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

 

Traveling From
Logan Intl.
Traveling To
Midway Intl.
Shortest Flight Time
0 hours 45 mins
Earliest Departure Time
7:00AM CST
Latest Departure Time
6:00PM CST
Lowest Flight Price
$110

Route Info

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


Origin:
BOS - Logan International Airport
Destination:
MDW - Chicago Midway International Airport
Distance:
863.00 miles


Discover our best flights from Boston BOS to Chicago MDW. 

With 20 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 $110 and $127. 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 $55. 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 Travelocity.com 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, December 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.