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$129 Cheap Flights from Chicago (MDW) to Boston (BOS)

View $129 flight on Sun, Nov 22, 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 $129 for one-way flights and $197 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Fri, Dec 4 - Mon, Dec 7
MDW
Chicago
BOS
Boston
$197 Roundtrip, found 2 days ago
$197
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Dec 4 from Chicago to Boston, returning Mon, Dec 7, priced at $197 found 2 days ago
Southwest Airlines
Thu, Dec 10 - Mon, Dec 14
MDW
Chicago
BOS
Boston
$207 Roundtrip, found 2 days ago
$207
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Dec 10 from Chicago to Boston, returning Mon, Dec 14, priced at $207 found 2 days ago
Southwest Airlines
Tue, Oct 27 - Sat, Oct 31
MDW
Chicago
BOS
Boston
$208 Roundtrip, found 2 days ago
$208
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Oct 27 from Chicago to Boston, returning Sat, Oct 31, priced at $208 found 2 days ago
Southwest Airlines
Sat, Oct 31 - Wed, Nov 18
MDW
Chicago
BOS
Boston
$208 Roundtrip, found 2 days ago
$208
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Oct 31 from Chicago to Boston, returning Wed, Nov 18, priced at $208 found 2 days ago
Southwest Airlines
Wed, Oct 28 - Fri, Oct 30
MDW
Chicago
BOS
Boston
$212 Roundtrip, found 2 days ago
$212
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Oct 28 from Chicago to Boston, returning Fri, Oct 30, priced at $212 found 2 days ago
Southwest Airlines
Tue, Oct 27 - Sat, Oct 31
MDW
Chicago
BOS
Boston
$217 Roundtrip, found 2 days ago
$217
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Oct 27 from Chicago to Boston, returning Sat, Oct 31, priced at $217 found 2 days ago
Southwest Airlines
Sat, Oct 31 - Wed, Nov 18
MDW
Chicago
BOS
Boston
$218 Roundtrip, found 2 days ago
$218
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Oct 31 from Chicago to Boston, returning Wed, Nov 18, priced at $218 found 2 days ago
Southwest Airlines
Tue, Oct 20 - Tue, Oct 27
MDW
Chicago
BOS
Boston
$222 Roundtrip, found 2 days ago
$222
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Oct 20 from Chicago to Boston, returning Tue, Oct 27, priced at $222 found 2 days ago
Southwest Airlines
Wed, Oct 28 - Fri, Oct 30
MDW
Chicago
BOS
Boston
$222 Roundtrip, found 2 days ago
$222
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Oct 28 from Chicago to Boston, returning Fri, Oct 30, priced at $222 found 2 days ago
Delta
Sat, Oct 3 - Tue, Oct 6
MDW
Chicago
BOS
Boston
$317 Roundtrip, found 5 hours ago
$317
Roundtrip
found 5 hours ago
Select Delta flight, departing Sat, Oct 3 from Chicago to Boston, returning Tue, Oct 6, priced at $317 found 5 hours ago

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 $275
BOS
Logan Intl.
CheapestClosest
Average driving time to city center7 min
Flights from $275

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

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

Travel between Chicago (MDW) and Boston (BOS) with a variety of airlines on this domestic short-haul route. Explore options for flights from Chicago, including both full-service and budget carriers, to discover the itinerary that aligns with your travel plans and budget. As you prepare to uncover Boston’s iconic landmarks and vibrant neighborhoods, gather all the essential details for your flight from Midway International Airport (MDW) to Logan International Airport (BOS).

  • Fastest flight duration: around 2h 15m non-stop
  • Route distance: roughly 900 miles (1,450 km)
  • Flights per week: around 15+ flights with multiple daily departures on average
  • Typical fares (one-way): economy tickets often range from $50–$295, depending on seasonality and how far ahead you book

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

Based on the latest traveler bookings, we've compiled a list of the most favored airlines flying from Chicago to Boston, particularly for non-stop and one-stop options. Common layover points include Detroit Metropolitan Wayne County Airport (DTW) with a layover of about 1 hour and 15 minutes, Baltimore Washington International Thurgood Marshall Airport (BWI) at approximately 1 hour and 30 minutes, and Lambert-St. Louis International Airport (STL), also around 1 hour and 15 minutes. This selection allows you to balance price, total travel time, and cabin class to find your ideal itinerary.

  • Southwest Airlines: This budget-friendly airline provides both direct and one-stop flights, with one-way fares generally falling between $50 and $295. It operates about 96% of the departures on this route, and the average non-stop flight duration is approximately 2 hours and 15 minutes.
  • Delta: As a traditional full-service airline, Delta offers one-stop options with one-way fares that typically range from $70 to $340. It represents around 4% of the departures for this route, featuring an in-flight duration of 3 hours and 30 minutes, culminating in a total travel time of about 5 hours, including layover.

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

The most popular months for travelers flying from Chicago to Boston are March, April, and October, when peak temperatures in Boston reach up to 55.6°F in October. If you prefer quieter travel, consider January, the least busy time to visit with temperatures around 30°F and typically the lowest average one-way fare (around $118). Flight availability peaks in July, with approximately 26 flights per week, making it easier to find convenient departure times. February has the fewest flights, with approximately 12 flights per week.

  • Cheapest time to fly: January usually offers good deals with average one-way fare around $118, roughly 16% cheaper than the yearly average.
  • More budget-friendly months to fly: February and June typically offer average one-way fares of around $125.
  • Most flight options: July has the highest number of flights from Chicago to Boston, with approximately 26 flights per week, giving you more flexibility in scheduling your trip.
calendar iconMonthtemperature iconTemperaturecrowd level iconDemandflights iconWeekly Flightsprice iconAverage one-way Fare
January30.0°F (-1.1°C)Low13$118
February31.5°F (-0.3°C)Low12$122
March37.9°F (3.3°C)High18$164
April48.2°F (9.0°C)High19$151
May58.5°F (14.7°C)Average20$154
June66.6°F (19.2°C)Average23$128
July73.6°F (23.1°C)Average26$136
August72.7°F (22.6°C)Average21$147
September65.7°F (18.7°C)Low19$137
October55.6°F (13.1°C)High24$144
November44.4°F (6.9°C)Average21$153
December36.3°F (2.4°C)Average19$144

*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 Chicago (MDW) to Boston (BOS)

  • Chicago to Boston (ORD-BOS): O'Hare International Airport (ORD) is positioned roughly 16 miles from Midway International Airport (MDW). On this route, one-way economy fares generally fall between $60 and $270, influenced by the season and how far in advance you book. Travelers can choose between both non-stop and one-stop flights. Major airlines operating on this route include American Airlines and United. Additionally, first-class service is offered on this route.

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

Getting some of the best deals on flights from Chicago to Boston 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 usually available when booking at least two months in advance, although most travelers tend to book between two to eight weeks ahead. Departures in the morning, from 5 AM to 12 PM, often provide lower prices and are also the most popular times. Additionally, flying on Monday generally offers cheaper rates, while Sunday remains the most popular 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 Logan International Airport from Midway International Airport

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

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Boston, with private rides that can be arranged in advance.
  • Car rental: Renting a car from Logan International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Logan 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 Logan International Airport, Airport Station, a metro station, is located about 0.9 miles from the airport by car, while Chelsea Station, a train station, is about 2.8 miles away by car. Additionally, Boston Seaport, a seaport, is situated approximately 3.1 miles from the airport, also accessible by car.

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 $129 and cheap return flights from $197 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
$197
Distance
857 mi
Average flight time
3 hours 20 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 December. 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 $129 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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