$76 Cheap Flights from Chicago (MDW) to Boston (BOS)

View $76 flight on Wed, Apr 29, 2026Opens in a new window

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

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Cheap Flights from Chicago to Boston (MDW-BOS)

Prices were available within the past 7 days and start at $76 for one-way flights and $140 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Fri, May 8 - Tue, May 12
MDW
Chicago
BOS
Boston
$140 Roundtrip, just found
$140
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, May 8 from Chicago to Boston, returning Tue, May 12, priced at $140 just found
Frontier Airlines
Tue, May 5 - Tue, May 12
MDW
Chicago
BOS
Boston
$150 Roundtrip, found 1 day ago
$150
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, May 5 from Chicago to Boston, returning Tue, May 12, priced at $150 found 1 day ago
Southwest Airlines
Tue, Apr 28 - Wed, Apr 29
MDW
Chicago
BOS
Boston
$154 Roundtrip, found 1 day ago
$154
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Apr 28 from Chicago to Boston, returning Wed, Apr 29, priced at $154 found 1 day ago
Southwest Airlines
Thu, May 7 - Wed, May 13
MDW
Chicago
BOS
Boston
$159 Roundtrip, found 3 hours ago
$159
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Thu, May 7 from Chicago to Boston, returning Wed, May 13, priced at $159 found 3 hours ago
Frontier Airlines
Wed, May 13 - Tue, May 19
MDW
Chicago
BOS
Boston
$159 Roundtrip, found 1 hour ago
$159
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, May 13 from Chicago to Boston, returning Tue, May 19, priced at $159 found 1 hour ago
Frontier Airlines
Fri, May 8 - Mon, May 11
MDW
Chicago
BOS
Boston
$160 Roundtrip, found 2 hours ago
$160
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Fri, May 8 from Chicago to Boston, returning Mon, May 11, priced at $160 found 2 hours ago
Frontier Airlines
Mon, May 4 - Thu, May 7
MDW
Chicago
BOS
Boston
$166 Roundtrip, found 15 hours ago
$166
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Mon, May 4 from Chicago to Boston, returning Thu, May 7, priced at $166 found 15 hours ago
Southwest Airlines
Tue, May 12 - Wed, May 27
MDW
Chicago
BOS
Boston
$167 Roundtrip, just found
$167
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, May 12 from Chicago to Boston, returning Wed, May 27, priced at $167 just found
Southwest Airlines
Thu, May 7 - Wed, May 13
MDW
Chicago
BOS
Boston
$169 Roundtrip, found 3 hours ago
$169
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Thu, May 7 from Chicago to Boston, returning Wed, May 13, priced at $169 found 3 hours ago
Delta
Fri, May 1 - Sun, May 3
MDW
Chicago
BOS
Boston
$315 Roundtrip, just found
$315
Roundtrip
just found
Select Delta flight, departing Fri, May 1 from Chicago to Boston, returning Sun, May 3, priced at $315 just found

Alternative airports near Boston

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

Select flight to Logan Intl. BOS. Cheapest and Closest option available. Average driving time to city center is 7 minutes. Flights from $372
BOS
Logan Intl.
CheapestClosest
Average driving time to city center7 min
Flights from $372

Frequently asked questions

How much does a flight from Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan Intl.) cost?
You can find cheap one-way flights from $76 and cheap return flights from $140 Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan Intl.) with Expedia. One-way flights typically cost between $120 and $563, and return flights often range between $200 and $762. 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 the cheapest fares first, and use the Price Tracking tool to receive alerts when Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan Intl.)?
January is the cheapest month to fly from Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan Intl.), with average round-trip fares around $202. This price is about 29% lower than the average throughout the year, likely due to lower travel demand in winter. Other budget-friendly months include February and May.*Averages based on flights available on Expedia in the last year.
Which airlines fly direct from Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan Intl.)?
Enter MDW to BOS and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
How do I find cheap flights from Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan Intl.)?
To find a cheap flight from Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan 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 Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan Intl.)?
The best airline to fly with from Chicago, IL (MDW) to Boston, MA (BOS) will differ from traveler to traveler. If you like to fly early, WN offers early morning flights. If price is the most important factor, WN typically offers the lowest fares. WN offers the most daily flights from MDW to BOS, 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 Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan Intl.)?
The best time to fly from Chicago, IL (MDW) to Boston, MA (BOS) is typically in January and February. You can find return flights for around $202 during these months. Traveling in January and February often means lower prices and less crowded flights, making it a smart choice for budget-conscious travelers.*Prices based on flights available on Expedia in the last year.
How many flights per day from Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan Intl.)?
On average, there are around 4 nonstop flights per day from Midway Intl. (MDW) to Logan Intl. (BOS). For more options, look at flights that include layovers.
What is the earliest flight from Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan Intl.)?
The earliest flight from Chicago (Midway International Airport) to Boston (Logan International Airport) usually leaves at 5:00 AM. This early departure can help you maximize your day in Boston, giving you more time to explore the city. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan Intl.)?
The most popular departure times for flights from Chicago Midway International Airport (MDW) to Boston Logan International Airport (BOS) are in the late morning, from 9am to noon. About 29% of passengers prefer this time window. Many major carriers, including Delta, Southwest and Southwest, offer flights during this window. This timing works well because it allows you to arrive in Boston with plenty of time to enjoy the afternoon.
How long does it take to fly from Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan Intl.)?
Direct flights from MDW to BOS usually take about 2 hours 20 minutes, traveling roughly 857 miles. If you opt for a connecting flight, expect to add around 3 hours 30 minutes to your journey. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan Intl.)?
First class seats are offered on the MDW to BOS route with Delta Air Lines.
How do I earn miles on a Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan Intl.) flight with Expedia?
It's easy to earn miles on a Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan 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 Boston from Midway Intl. (MDW)?
From Midway Intl. (MDW), you can fly into Logan Intl. (BOS) to reach Boston. Some flights may connect through major hubs like Hartsfield-Jackson Atlanta Intl. (ATL), Detroit Metropolitan Wayne County (DTW), Louisville Intl. (SDF) before reaching Boston. 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 Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan Intl.) at the last minute?
Typically, booking a last minute flight from Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan 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 Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan Intl.) flight and hotel package?
Securing a Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan Intl.) Boston Vacation Packages 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 Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan Intl.)?
If you booked your Chicago, IL (MDW-Midway Intl.) to Boston, MA (BOS-Logan 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
Midway Intl.
Destination airport
Logan Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$140
Distance
857 mi
Average flight time
3 hours 16 mins

Book with confidence

Chicago to Boston Flights

The cheapest times to fly from Chicago to Boston

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 Chicago to Boston are during the month of May. You can find some of the cheapest flights from Chicago to Boston with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Boston

Sunday is one of the best days to book for cheap flights from Chicago to Boston: 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 Chicago to Boston

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 Chicago to Boston in 2026. You can also book with separate airlines for your outbound and return journeys, from $76 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 Chicago to Boston 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 Chicago to Boston 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.

 

Chicago to Boston Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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