--- title: "Chicago to Boston cheap flights from $116 (MDW to BOS) - Expedia" description: "Cheap Flights from Chicago (MDW) to Boston (BOS) start at $116 for one-way and $220 for round trip. Earn your airline miles on top of our rewards!" canonical: "https://www.expedia.com/lp/flights/mdw/bos/chicago-to-boston" language: en-US market: US currency: USD prices_as_of: 2026-11-15T19:04:32Z --- # $116 Cheap Flights from Chicago (MDW) to Boston (BOS) ![A city street with a historic building labeled 'QUINCY MARKET,' trees with autumn leaves, and modern high-rise buildings.](https://images.trvl-media.com/place/5459778/1efe54a0-5011-4269-b6c4-92db64d64036.jpg?impolicy=fcrop&w=1200&h=500&q=medium) [View $116 flight on Sat, Dec 19, 2026](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:BOS,departure:12/19/2026TANYT&trip=oneway&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:115.59&airProductToken=AQpgCi4IxnISBDE0NTgY7LABIMxwKJuhoAMwxaKgAzhSQABYAWoDRUNPcgdSMjFPWFA0Ci4IxnISBDMzNDgYzHAgwZMBKK2loAMw5qagAzhSQAFYAWoDRUNPcgdSMjFPWFA0EgoIARABGAEqAkY5GAEiBAgBEAEoAigDKAQwAQ) ## Popular airlines from Chicago Midway Airport (MDW) to Logan International Airport (BOS) [Southwest Airlines](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:BOS,departure:11/29/2026TANYT&leg2=from:BOS,to:MDW,departure:12/6/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) [Delta](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:BOS,departure:11/29/2026TANYT&leg2=from:BOS,to:MDW,departure:12/6/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) [Frontier Airlines](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:BOS,departure:11/29/2026TANYT&leg2=from:BOS,to:MDW,departure:12/6/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) ### Be in the know Get alerts if flight prices drop or rise\* ### Book smarter Save up to 30% on select hotels after you book a flight\* ### Earn twice Earn your airline miles on top of our OneKeyCash [Learn about One Key](https://www.expedia.com/welcome-one-key) ## Cheap Flights from Chicago to Boston (MDW-BOS) Prices were available within the past 7 days and start at $116 for one-way flights and $220 for roundtrip, for the period specified. Prices and availability are subject to change. All deals One way Roundtrip [Select Frontier Airlines flight, departing Sat, Dec 19 from Chicago to Boston, returning Tue, Jan 5, priced at $220 Found 6 hours ago](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:BOS,departure:12/19/2026TANYT&leg2=from:BOS,to:MDW,departure:1/5/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:219.97&airProductToken=AQpgCi4IxnISBDE0NTgY7LABIMxwKJuhoAMwxaKgAzhSQABYAWoDRUNPcgdSMjFPWFA0Ci4IxnISBDMzNDgYzHAgwZMBKK2loAMw5qagAzhSQAFYAWoDRUNPcgdSMjFPWFA0CmAKLgjGchIEMTc3MxjBkwEg4FwostqhAzD326EDOFJAAFgBagNFQ09yB1IyMU9YUDQKLgjGchIEMjc3ORjgXCDssAEo3d2hAzDW3qEDOFJAAVgBagNFQ09yB1IyMU9YUDQSCggBEAEYASoCRjkYASIECAEQASgCKAMoBDAB) Sat, Dec 19 - Tue, Jan 5 · MDW · BOS · Roundtrip [Select Southwest Airlines flight, departing Fri, Dec 25 from Chicago to Boston, returning Tue, Jan 5, priced at $229 Found 1 day ago](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:BOS,departure:12/25/2026TANYT&leg2=from:BOS,to:MDW,departure:1/5/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:228.39&airProductToken=AQoyCjAI15wBEgQyOTAyGOywASDBkwEo2eOgAzDl5KADOFZAAFgBagNXR0FyB1ZMTlZIMkYSCggBEAEYASoCV04YASIECAEQASgCKAMoBDAB) Fri, Dec 25 - Tue, Jan 5 · MDW · BOS · Roundtrip [Select Southwest Airlines flight, departing Thu, Dec 17 from Chicago to Boston, returning Wed, Jan 6, priced at $234 Found 6 hours ago](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:BOS,departure:12/17/2026TANYT&leg2=from:BOS,to:MDW,departure:1/6/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:233.38&airProductToken=AQoyCjAI15wBEgQyOTAyGOywASDBkwEo7YmgAzD5iqADOERAAFgBagNXR0FyB0RMTlZIMkYSCggBEAEYASoCV04YASIECAEQASgCKAMoBDAB) Thu, Dec 17 - Wed, Jan 6 · MDW · BOS · Roundtrip [Select Southwest Airlines flight, departing Fri, Dec 25 from Chicago to Boston, returning Tue, Jan 5, priced at $239 Found 1 day ago](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:BOS,departure:12/25/2026TANYT&leg2=from:BOS,to:MDW,departure:1/5/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:238.19&airProductToken=AQpiCi8I15wBEgQyNzM3GOywASDyXCi14KADMPvgoAM4VkAAWAFqA1dHQXIHVkxBVkgyRgovCNecARIEMzY2NxjyXCDBkwEoo-GgAzC54qADOFZAAVgBagNXR0FyB1ZMQVZIMkYSCggBEAEYASoCV04YASIECAEQASgCKAMoBDAB) Fri, Dec 25 - Tue, Jan 5 · MDW · BOS · Roundtrip [Select Frontier Airlines flight, departing Tue, Feb 16 from Chicago to Boston, returning Wed, Feb 17, priced at $240 Found 2 hours ago](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:BOS,departure:2/16/2027TANYT&leg2=from:BOS,to:MDW,departure:2/17/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:239.98&airProductToken=AQpgCi4IxnISBDE0NTgY7LABIMxwKIe5pQMwsbqlAzhHQABYAWoDRUNPcgdHMTRPWFA0Ci4IxnISBDMzNDgYzHAgwZMBKIy9pQMwxb6lAzhHQAFYAWoDRUNPcgdHMTRPWFA0CmAKLgjGchIEMzM0NxjBkwEgzHAo%5FL6lAzDbwKUDOFJAAFgBagNFQ09yB1IyMU9YUDQKLgjGchIEMTQ1NxjMcCDssAEoscKlAzDmw6UDOFJAAVgBagNFQ09yB1IyMU9YUDQSCggBEAEYASoCRjkYASIECAEQASgCKAMoBDAB) Tue, Feb 16 - Wed, Feb 17 · MDW · BOS · Roundtrip [Select Frontier Airlines flight, departing Sat, Dec 19 from Chicago to Boston, returning Mon, Jan 18, priced at $241 Found 20 hours ago](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:BOS,departure:12/19/2026TANYT&leg2=from:BOS,to:MDW,departure:1/18/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:240.98&airProductToken=AQpECiAIxnISBDE0NTgY7LABIMxwKJuhoAMwxaKgAzhSQABYAQogCMZyEgQzMzQ4GMxwIMGTASitpaADMOamoAM4UkABWAEKRAogCMZyEgQxNzczGMGTASDgXCjK7KIDMI3uogM4R0AAWAEKIAjGchIEMjc3ORjgXCDssAEo3u-iAzDa8KIDOEdAAVgBEgoIARABGAEqAkY5GAEiBAgBEAEoBDAB) Sat, Dec 19 - Mon, Jan 18 · MDW · BOS · Roundtrip [Select Southwest Airlines flight, departing Thu, Dec 17 from Chicago to Boston, returning Wed, Jan 6, priced at $244 Found 6 hours ago](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:BOS,departure:12/17/2026TANYT&leg2=from:BOS,to:MDW,departure:1/6/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:243.18&airProductToken=AQpiCi8I15wBEgQzMDQyGOywASDyXCiOhKADMNmEoAM4REAAWAFqA1dHQXIHRExBVkgyRgovCNecARIENDkxOBjyXCDBkwEo74WgAzCFh6ADOERAAVgBagNXR0FyB0RMQVZIMkYSCggBEAEYASoCV04YASIECAEQASgCKAMoBDAB) Thu, Dec 17 - Wed, Jan 6 · MDW · BOS · Roundtrip [Select Frontier Airlines flight, departing Sat, Dec 19 from Chicago to Boston, returning Tue, Dec 22, priced at $244 Found 18 hours ago](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:BOS,departure:12/19/2026TANYT&leg2=from:BOS,to:MDW,departure:12/22/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:243.99&airProductToken=AQpgCi4IxnISBDE0NTgY7LABIMxwKJuhoAMwxaKgAzhSQABYAWoDRUNPcgdSMjFPWFA0Ci4IxnISBDMzNDgYzHAgwZMBKK2loAMw5qagAzhSQAFYAWoDRUNPcgdSMjFPWFA0EgwIARABGAEqAkY5MgAYASIECAEQASgCKAMoBDAB) Sat, Dec 19 - Tue, Dec 22 · MDW · BOS · Roundtrip [Select Southwest Airlines flight, departing Fri, Dec 25 from Chicago to Boston, returning Tue, Dec 29, priced at $247 Found 4 hours ago](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:BOS,departure:12/25/2026TANYT&leg2=from:BOS,to:MDW,departure:12/29/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:246.81&airProductToken=AQoyCjAI15wBEgQyOTAyGOywASDBkwEo2eOgAzDl5KADOFZAAFgBagNXR0FyB1ZMTlZIMkYKMQovCNecARIDODE2GMGTASDssAEojZKhAzDBk6EDOFZAAFgBagNXR0FyB1ZMTlZIMkYSCggBEAEYASoCV04YASIECAEQASgCKAMoBDAB) Fri, Dec 25 - Tue, Dec 29 · MDW · BOS · Roundtrip [Select Delta flight, departing Tue, Dec 22 from Chicago to Boston, returning Wed, Jan 6, priced at $264 Found 3 hours ago](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:BOS,departure:12/22/2026TANYT&leg2=from:BOS,to:MDW,departure:1/6/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:263.18&airProductToken=AQpyCjcIxJgBEgQ0NjkwGOywASDjtAEo78GgAzC-wqADOEVAAFgBaglNQUlOQkFTSUNyCFZBVlNBMEJDCjcIxJgBEgQxMTg3GOO0ASDBkwEok8OgAzCLxKADOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNBMEJDEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) Tue, Dec 22 - Wed, Jan 6 · MDW · BOS · Roundtrip ## 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 $462](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:BOS,departure:11/29/2026TANYT&leg2=from:BOS,to:MDW,departure:12/6/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) 7 min ## Find the cheapest month to fly from Chicago (MDW) to Boston (BOS) ### July is typically the cheapest month to fly From $183 - $336 per traveler. View flights in July Insights are based on prices from searches for economy trips of 10 days or less on our sites in the last 12 months. Insights are informative only and current prices may differ. ## Book with confidence ### 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](https://www.expedia.com/southwest-airlines-flights.cwn.travel-guide-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](https://www.expedia.com/lp/flight-routes/delta-from-midway-intl-to-logan-intl/dl/mdw/bos)**: 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. | **Month** | **Temperature** | **Demand** | **Weekly Flights** | **Average one-way Fare** | | --------- | --------------- | ---------- | ------------------ | ------------------------ | | January | 30.0°F (-1.1°C) | Low | 13 | $118 | | February | 31.5°F (-0.3°C) | Low | 12 | $122 | | March | 37.9°F (3.3°C) | High | 18 | $164 | | April | 48.2°F (9.0°C) | High | 19 | $151 | | May | 58.5°F (14.7°C) | Average | 20 | $154 | | June | 66.6°F (19.2°C) | Average | 23 | $128 | | July | 73.6°F (23.1°C) | Average | 26 | $136 | | August | 72.7°F (22.6°C) | Average | 21 | $147 | | September | 65.7°F (18.7°C) | Low | 19 | $137 | | October | 55.6°F (13.1°C) | High | 24 | $144 | | November | 44.4°F (6.9°C) | Average | 21 | $153 | | December | 36.3°F (2.4°C) | Average | 19 | $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](https://www.expedia.com/lp/flights/ord/bos/chicago-to-boston))**: 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](https://www.expedia.com/flight-deals) 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](https://www.expedia.com/why/price-tracking). 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](https://www.expedia.com/car-rentals-in-logan-intl.d5459778.car-rental-guide) 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. ### 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 $116 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](https://www.expedia.com/package-deals). 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.* ## 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 $116 and cheap return flights $220 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](https://www.expedia.com/why/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™](https://www.expedia.com/welcome-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](https://www.expedia.com/boston.d178239.destination-travel-guides) 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](https://www.expedia.com/trips) or confirmation email. Or, head to our [Customer Service portal](https://www.expedia.com/helpcenter/) if you'd like more information. ## Travel information | Origin airport | Chicago Midway Airport | | ------------------- | -------------------------------------------- | | Destination airport | Logan International Airport | | Distance | 857 miles away | | Airlines serving | Southwest Airlines, Delta, Frontier Airlines | | Popular airline | Southwest Airlines | | Roundtrip price | $220 | | Average flight time | 2 hours 17 mins | ## Explore a world of travel with Expedia - [Flights](?equalTargetTab=tab-0) - [Flights from San Diego (SAN) to Boston (BOS)](https://www.expedia.com/lp/flights/san/bos/san-diego-to-boston) - [Flights from London (LHR) to Boston (BOS)](https://www.expedia.com/lp/flights/lhr/bos/london-to-boston) - [Flights from Madrid (MAD) to Boston (BOS)](https://www.expedia.com/lp/flights/mad/bos/madrid-to-boston) - [Flights from Paris (CDG) to Boston (BOS)](https://www.expedia.com/lp/flights/cdg/bos/paris-to-boston) - [Flights from Honolulu (HNL) to Boston (BOS)](https://www.expedia.com/lp/flights/hnl/bos/honolulu-to-boston) - [Flights from San Francisco (SFO) to Boston (BOS)](https://www.expedia.com/lp/flights/sfo/bos/san-francisco-to-boston) - [Flights from Baltimore (BWI) to Boston (BOS)](https://www.expedia.com/lp/flights/bwi/bos/baltimore-to-boston) - [Flights from Buffalo (BUF) to Boston (BOS)](https://www.expedia.com/lp/flights/buf/bos/buffalo-to-boston) - [Flights from Barcelona (BCN) to Boston (BOS)](https://www.expedia.com/lp/flights/bcn/bos/barcelona-to-boston) - [Flights from San Jose (SJC) to Boston (BOS)](https://www.expedia.com/lp/flights/sjc/bos/san-jose-to-boston) - [Flights from New York (NYC) to Boston (BOS)](https://www.expedia.com/lp/flights/nyc/bos/new-york-to-boston) - [Flights from Des Moines (DSM) to Boston (BOS)](https://www.expedia.com/lp/flights/dsm/bos/des-moines-to-boston) - [Flights from Cleveland (CLE) to Boston (BOS)](https://www.expedia.com/lp/flights/cle/bos/cleveland-to-boston) - [Flights from Denver (DEN) to Boston (BOS)](https://www.expedia.com/lp/flights/den/bos/denver-to-boston) - [Flights from Lisbon (LIS) to Boston (BOS)](https://www.expedia.com/lp/flights/lis/bos/lisbon-to-boston) - [Flights from Detroit (DTW) to Boston (BOS)](https://www.expedia.com/lp/flights/dtw/bos/detroit-to-boston) - [Flights from Philadelphia (PHL) to Boston (BOS)](https://www.expedia.com/lp/flights/phl/bos/philadelphia-to-boston) - [Flights from Athens (ATH) to Boston (BOS)](https://www.expedia.com/lp/flights/ath/bos/athens-to-boston) - [Flights from Tucson (TUS) to Boston (BOS)](https://www.expedia.com/lp/flights/tus/bos/tucson-to-boston) - [Flights from Washington (IAD) to Boston (BOS)](https://www.expedia.com/lp/flights/iad/bos/washington-to-boston) - [Flights from Ontario Intl. 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[Flights from Fort Lauderdale (FLL) to Boston (BOS)](https://www.expedia.com/lp/flights/fll/bos/fort-lauderdale-to-boston) - [Flights from Indianapolis (IND) to Boston (BOS)](https://www.expedia.com/lp/flights/ind/bos/indianapolis-to-boston) - [Flights from Ithaca (ITH) to Boston (BOS)](https://www.expedia.com/lp/flights/ith/bos/ithaca-to-boston) - [Flights from Austin (AUS) to Boston (BOS)](https://www.expedia.com/lp/flights/aus/bos/austin-to-boston) - [Flights from Miami (MIA) to Boston (BOS)](https://www.expedia.com/lp/flights/mia/bos/miami-to-boston) \*Available to One Key members. ## Other language versions ```yaml hreflang: x-default: https://www.expedia.com/lp/flights/mdw/bos/chicago-to-boston en-NZ: https://www.expedia.co.nz/lp/flights/mdw/bos/chicago-to-boston en-GB: https://www.expedia.co.uk/lp/flights/mdw/bos/chicago-to-boston es: https://www.expedia.com/es/lp/vuelos/mdw/bos/chicago-a-boston pt-BR: https://www.expedia.com.br/lp/voos/mdw/bos/chicago-para-boston de-CH: https://www.expedia.ch/lp/fluege/mdw/bos/chicago-nach-boston en-IN: https://www.expedia.co.in/lp/flights/mdw/bos/chicago-to-boston en-TW: https://www.expedia.com.tw/en/lp/flights/mdw/bos/chicago-to-boston de-DE: https://www.expedia.de/lp/fluge/mdw/bos/chicago-nach-boston en-US: https://www.expedia.com/lp/flights/mdw/bos/chicago-to-boston ar: https://www.expedia.sa/lp/flights/mdw/bos/chicago-to-boston sv-SE: https://www.expedia.se/lp/flyg/mdw/bos/chicago-till-boston nl-BE: https://www.expedia.be/lp/vluchten/mdw/bos/chicago-naar-boston nb-NO: https://www.expedia.no/lp/fly/mdw/bos/chicago-til-boston fr-BE: https://www.expedia.be/fr/lp/vols/mdw/bos/chicago-a-boston ```