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CA $187 Cheap Flights from Boston (BOS) to Chicago (MDW)

View CA $187 flight on Fri, Aug 14, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at CA $187 for one-way flights and CA $444 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Aug 26 - Mon, Aug 31
BOS
Boston
MDW
Chicago
CA $444 Roundtrip, found 7 hours ago
CA $444
Roundtrip
found 7 hours ago
Select Delta flight, departing Wed, Aug 26 from Boston to Chicago, returning Mon, Aug 31, priced at CA $444 found 7 hours ago
Southwest Airlines
Sun, Aug 16 - Sun, Aug 23
BOS
Boston
MDW
Chicago
CA $449 Roundtrip, found 2 hours ago
CA $449
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Sun, Aug 16 from Boston to Chicago, returning Sun, Aug 23, priced at CA $449 found 2 hours ago
Delta
Mon, Aug 3 - Fri, Aug 7
BOS
Boston
MDW
Chicago
CA $460 Roundtrip, found 6 days ago
CA $460
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Aug 3 from Boston to Chicago, returning Fri, Aug 7, priced at CA $460 found 6 days ago
Southwest Airlines
Sun, Aug 16 - Sun, Aug 23
BOS
Boston
MDW
Chicago
CA $464 Roundtrip, found 2 hours ago
CA $464
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Sun, Aug 16 from Boston to Chicago, returning Sun, Aug 23, priced at CA $464 found 2 hours ago
Delta
Fri, Aug 14 - Tue, Aug 18
BOS
Boston
MDW
Chicago
CA $489 Roundtrip, found 6 days ago
CA $489
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Aug 14 from Boston to Chicago, returning Tue, Aug 18, priced at CA $489 found 6 days ago
Delta
Mon, Aug 3 - Fri, Aug 7
BOS
Boston
MDW
Chicago
CA $495 Roundtrip, found 6 days ago
CA $495
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Aug 3 from Boston to Chicago, returning Fri, Aug 7, priced at CA $495 found 6 days ago
Southwest Airlines
Sun, Aug 16 - Sun, Aug 23
BOS
Boston
MDW
Chicago
CA $506 Roundtrip, found 2 hours ago
CA $506
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Sun, Aug 16 from Boston to Chicago, returning Sun, Aug 23, priced at CA $506 found 2 hours ago
Southwest Airlines
Sun, Aug 16 - Sun, Aug 23
BOS
Boston
MDW
Chicago
CA $520 Roundtrip, found 2 hours ago
CA $520
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Sun, Aug 16 from Boston to Chicago, returning Sun, Aug 23, priced at CA $520 found 2 hours ago
Delta
Mon, Aug 3 - Fri, Aug 7
BOS
Boston
MDW
Chicago
CA $524 Roundtrip, found 6 days ago
CA $524
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Aug 3 from Boston to Chicago, returning Fri, Aug 7, priced at CA $524 found 6 days ago
Delta
Mon, Aug 3 - Fri, Aug 7
BOS
Boston
MDW
Chicago
CA $537 Roundtrip, found 6 days ago
CA $537
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Aug 3 from Boston to Chicago, returning Fri, Aug 7, priced at CA $537 found 6 days ago

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. Cheapest option available. Average driving time to city centre is 23 minutes. Flights from CA $380
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from CA $380

Frequently asked questions

How much does a flight from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find one-way and return flights from BOS to MDW with Expedia. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see our cheapest fares first, and use the Price Tracking tool to receive alerts when BOS to MDW ticket fares go up or down.
What is the cheapest month to fly from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.)?
The cheapest months to fly from BOS to MDW are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.)?
Only one airline offers direct flights from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.). Southwest Airlines operates 33 direct flights from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.) every week.
What is the cheapest airline that flies from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.)?
Southwest Airlines is one of the cheapest airlines offering nonstop return flights from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.), with tickets starting from around CA$134 for flights that can be booked for departure within the next year. Frontier Airlines offers one of the cheapest connecting return flights from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.) starting from around CA$177. These prices are per adult for economy/coach class. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.
How do I find cheap flights from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.)?
The best airline to fly with from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.) will differ from traveler to traveler. If you like to fly early, Southwest Airlines offers early morning flights. If price is the most important factor, Southwest Airlines typically offers the lowest fares. Southwest Airlines offers the most daily flights from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.), which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.)?
You'll find approximately 5 nonstop flights per day from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.). For even more choices, look at flights that include layovers, as there are around 44 connecting flights per day. Some common connection points include Baltimore Washington Intl. Thurgood Marshall (BWI), Lambert-St. Louis Intl. (STL), and Liberty Intl. (EWR).
What is the earliest flight from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.) typically departs around 5:00 AM local time, operated by Southwest Airlines. This is a seasonal service active in October. An early departure like this can help you make the most of your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.)?
You'll typically find the most flights from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.) on a Friday, with around 33 flights available. This gives you a good selection of options for your travel plans. Major airlines on this route include Southwest Airlines, Delta, and United. Flight options on Fridays are notably more plentiful compared to other days of the week, offering you greater flexibility.
What are the most popular departure times for flights from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.) are in the morning, from 9am to 12pm. Many major carriers, including Southwest Airlines, Delta and United, offer flights during this window. Many travellers prefer these times as they allow for an early start to their travel day, getting you to your destination with plenty of time left in the afternoon.
How long does it take to fly from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.)?
A nonstop flight from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.) typically takes around 2 hours 48 minutes. This route covers a distance of approximately 1,379 kilometers. If you opt for a one-stop flight, your travel time will be longer, usually around 6 hours. Flights with two or more stops can take significantly more time, often around 13 hours 18 minutes. Keep in mind that actual flight times can vary due to factors like wind patterns and air traffic.
Can you fly business or first class from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.)?
You can fly business class or first class between BOS and MDW. You can fly business class with Frontier Airlines and Delta.First class cabins are available on Delta.
How do I earn miles on a Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago, IL (MDW) from Boston, MA (BOS)?
If you're planning to travel to Chicago from Logan International Airport (BOS), you can fly directly into Midway International Airport (MDW). Some flights may connect through major hubs like Baltimore Washington International Thurgood Marshall (BWI), Liberty International Airport (EWR), or Nashville International Airport (BNA) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Logan Intl.
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
CA $444
Distance
1371 km
Average flight time
1 hour 33 mins

Book with confidence

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 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 $444 rising to CA $537.  

Here are more money-saving tips: 

  • Fly in August 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.

Boston to Chicago Flights

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