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$85 Cheap Flights from Boston (BOS) to Chicago (MDW)

View $85 flight on Tue, Nov 3, 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 to Chicago (BOS-MDW)

Prices were available within the past 7 days and start at $85 for one-way flights and $180 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Tue, Nov 17 - Wed, Nov 18
BOS
Boston
MDW
Chicago
$180 Roundtrip, found 4 hours ago
$180
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Tue, Nov 17 from Boston to Chicago, returning Wed, Nov 18, priced at $180 found 4 hours ago
Frontier Airlines
Thu, Dec 3 - Sun, Dec 6
BOS
Boston
MDW
Chicago
$180 Roundtrip, found 1 hour ago
$180
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Dec 3 from Boston to Chicago, returning Sun, Dec 6, priced at $180 found 1 hour ago
Southwest Airlines
Fri, Oct 23 - Mon, Oct 26
BOS
Boston
MDW
Chicago
$189 Roundtrip, just found
$189
Roundtrip
just found
Select Southwest Airlines flight, departing Fri, Oct 23 from Boston to Chicago, returning Mon, Oct 26, priced at $189 just found
Frontier Airlines
Mon, Dec 14 - Thu, Dec 31
BOS
Boston
MDW
Chicago
$196 Roundtrip, found 1 day ago
$196
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Dec 14 from Boston to Chicago, returning Thu, Dec 31, priced at $196 found 1 day ago
Frontier Airlines
Mon, Dec 7 - Thu, Dec 10
BOS
Boston
MDW
Chicago
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Dec 7 from Boston to Chicago, returning Thu, Dec 10, priced at $197 found 1 day ago
Southwest Airlines
Tue, Oct 20 - Wed, Oct 21
BOS
Boston
MDW
Chicago
$199 Roundtrip, just found
$199
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Oct 20 from Boston to Chicago, returning Wed, Oct 21, priced at $199 just found
Southwest Airlines
Fri, Oct 23 - Mon, Oct 26
BOS
Boston
MDW
Chicago
$202 Roundtrip, just found
$202
Roundtrip
just found
Select Southwest Airlines flight, departing Fri, Oct 23 from Boston to Chicago, returning Mon, Oct 26, priced at $202 just found
Southwest Airlines
Sat, Dec 5 - Mon, Dec 7
BOS
Boston
MDW
Chicago
$204 Roundtrip, found 1 day ago
$204
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Dec 5 from Boston to Chicago, returning Mon, Dec 7, priced at $204 found 1 day ago
Delta
Wed, Oct 14 - Wed, Oct 21
BOS
Boston
MDW
Chicago
$209 Roundtrip, found 1 day ago
$209
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Oct 14 from Boston to Chicago, returning Wed, Oct 21, priced at $209 found 1 day ago
Southwest Airlines
Wed, Oct 7 - Tue, Oct 13
BOS
Boston
MDW
Chicago
$209 Roundtrip, found 3 hours ago
$209
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Wed, Oct 7 from Boston to Chicago, returning Tue, Oct 13, priced at $209 found 3 hours 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 center is 23 minutes. Flights from $242
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $242

What you need to know for your flight from Logan Intl. to Midway Intl.

Boston (BOS) to Chicago (MDW) at a glance

Travel from Boston (BOS) to Chicago (MDW) with a variety of airlines catering to your travel needs on this domestic short-haul route. Whether you're looking for full-service options or budget-friendly choices, you can easily compare flights from Boston to Chicago to find the itinerary that suits your budget and schedule. Discover essential details for flights from Logan International Airport to Midway International Airport as you plan your visit to Chicago's iconic attractions and vibrant neighborhoods.

  • Fastest flight duration: around 2h 45m non-stop
  • Route distance: roughly 900 miles (1,450 km)
  • Flights per week: around 20+ flights with multiple daily departures on average
  • Typical fares (one-way): economy tickets often range from $50–$290, depending on seasonality and how far ahead you book

Flights from Logan International Airport (BOS) to Midway International Airport (MDW)

Based on recent traveler bookings, here are the top airlines favored for flights from Boston to Chicago, particularly for non-stop and one-stop options. Many travelers opt for layovers at Detroit Metropolitan Wayne County Airport (DTW, approximately 55 minutes), Baltimore Washington International Thurgood Marshall Airport (BWI, around 1 hour 30 minutes), and Lambert-St. Louis International Airport (STL, also about 1 hour 30 minutes). These choices allow you to mix and match price, overall travel time, and cabin class to create the ideal itinerary.

  • Southwest Airlines: This budget airline provides both non-stop and one-stop flights, with one-way prices generally falling between $50 and $290. It operates around 95% of the departures on this route, with non-stop travel taking about 2 hours and 45 minutes.
  • Delta: As a full-service airline, Delta offers one-stop journeys priced between $155 and $350 for one-way tickets. It represents about 5% of departures on this route, with an in-flight duration of 3 hours and 45 minutes, leading to an overall travel time of approximately 5 hours and 30 minutes including layovers.
  • Frontier Airlines: This low-cost airline features one-stop service options, with one-way fares typically ranging from $80 to $185. Passengers can expect an in-flight time of 3 hours and 45 minutes, culminating in a total journey duration of around 5 hours and 30 minutes when including layover time.

Best time to fly from Boston (BOS) to Chicago (MDW)

The most popular months for travelers flying from Boston to Chicago are April, July, and October, when peak temperatures in Chicago reach up to 73.4°F in July. If you prefer quieter travel, consider January, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 25.7°F. For better deals, January and September usually offer the lowest average one-way fares around $109. Flight availability peaks in July, with approximately 33 flights per week, making it easier to find convenient departure times. February has the fewest flights, with approximately 13 flights per week.

  • Cheapest time to fly: January and September usually offer good deals with average one-way fares around $109, roughly 19% cheaper than the yearly average.
  • Most flight options: July has the highest number of flights from Boston to Chicago, with approximately 33 flights per week, giving you more flexibility in scheduling your trip.
calendar iconMonthtemperature iconTemperaturecrowd level iconDemandflights iconWeekly Flightsprice iconAverage one-way Fare
January25.7°F (-3.5°C)Low14$109
February27.0°F (-2.8°C)Low13$124
March37.0°F (2.8°C)Average18$148
April46.0°F (7.8°C)High22$150
May57.0°F (13.9°C)Average20$128
June67.3°F (19.6°C)Average26$122
July73.4°F (23.0°C)High33$124
August73.0°F (22.8°C)Average26$132
September67.1°F (19.5°C)Average22$109
October54.9°F (12.7°C)High25$159
November42.3°F (5.7°C)Average26$160
December33.1°F (0.6°C)Low20$150

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

Alternative route from Boston (BOS) to Chicago (MDW)

  • Boston to Chicago (BOS-ORD): O'Hare International Airport (ORD) is located approximately 16 miles from Midway International Airport (MDW). One-way economy ticket prices on this route typically fall between $60 and $275, influenced by the time of year and how early you book. Travelers can choose from both non-stop and one-stop flights. Major airlines operating this route include American Airlines and United. Additionally, first-class service is offered for those looking for a more premium experience.

How to find the best prices for flights from Boston (BOS) to Chicago (MDW)

Getting some of the best deals on flights from Boston to Chicago is all about timing and flexibility. Here are some key tips to help you save:

  1. Best times to book and fly: cheaper fares are typically found when booking 2-8 weeks in advance, which coincides with when most travelers make their reservations. Afternoon departures (12 p.m. to 6 p.m.) often offer lower prices, although morning flights (5 a.m. to 12 p.m.) are the most popular. Additionally, flying on Thursday generally results in cheaper prices, while Friday remains the most favored travel day.
  2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
  3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
  4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
  6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at Midway International Airport from Logan International Airport

Chicago welcomes travelers from Boston with a range of transport options based on price, convenience, and proximity. Here's how to reach Chicago efficiently:

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Chicago, with private rides that can be arranged in advance.
  • Car rental: Renting a car from Midway International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Midway International Airport on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
  • Public transportation: From Midway International Airport, travelers will find Midway Station, a metro station located about 0.2 miles away on foot, providing easy access to public transit. For those needing rail services, Chicago Ashburn Station, a train station, is about 4.1 miles from the airport by car, while Lyons Seaport, a seaport, is approximately 7.2 miles away by car.

Frequently asked questions

How much does a flight from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights from $85 and cheap return flights from $180 Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.) with Expedia. One-way flights typically cost between $98 and $565, and return flights often range between $202 and $814. 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 Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway 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 Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.)?
The cheapest month to fly from BOS to MDW is November 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're 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.)?
Enter BOS to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
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 flights from Boston (BOS) to Chicago (MDW), with round-trip tickets starting from around $67. 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.*Prices based on flights available on Expedia in the last year.
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) to Chicago, IL (MDW) 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 BOS to MDW, 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 can find approximately 4 nonstop flights per day from Logan Intl. (BOS) to Midway Intl. (MDW). For more options, look at flights that include layovers.
What is the earliest flight from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Boston (BOS) to Chicago (MDW) typically departs at around 5:00 AM, operated by Southwest Airlines. An early flight like this allows you to arrive in Chicago with a full day ahead of you. 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 Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Boston (BOS) to Chicago (MDW) are in the early morning, from 3am to 6am. About 23% of passengers prefer this time window. Many major carriers, including Delta and Southwest Airlines, offer flights during this window. This timing works well because it allows you to arrive in Chicago by morning, giving you a full day to enjoy the city.
How long does it take to fly from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.)?
A nonstop flight from BOS to MDW typically takes around 2 hours 50 minutes, covering approximately 857 miles. Connecting flights on this route usually add 5 hours 10 minutes to your travel time. 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 Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.)?
Select the "Business class" and "First class" filters when looking for BOS to MDW flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
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 from Logan Intl. (BOS)?
When traveling from Logan Intl. (BOS) to Chicago, you can fly into Midway Intl. (MDW) and O'Hare Intl. (ORD). Some flights may connect through major hubs like Baltimore Washington Intl. Thurgood Marshall (BWI), Nashville Intl. (BNA), Liberty Intl. (EWR) 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.) Chicago 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 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, Frontier Airlines, Southwest Airlines
Roundtrip price
$179
Distance
857 mi
Average flight time
1 hour 34 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 November. 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 2026. You can also book with separate airlines for your outbound and return journeys, from $85 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

*Flight schedules are subject to change.

*Available to One Key members.

 

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