Southwest Boston to Chicago – BOS to MDW

Southwest Boston to Chicago

If you’re planning a trip from Boston to Chicago, Southwest Airlines offers a convenient and reliable travel option. This article will guide you through the details of Southwest Airlines’ Boston to Chicago route, covering essential information such as flight schedules, ticket prices, amenities, and more. Whether you’re traveling for business or pleasure, Southwest Airlines ensures a comfortable and enjoyable journey from BOS to MDW.

Southwest Boston to Chicago Flight Schedule

Southwest Airlines offers multiple daily flights from Boston Logan International Airport (BOS) to Chicago Midway International Airport (MDW). The flight schedule is designed to accommodate various travel preferences, ensuring flexibility for passengers.

Southwest Boston to Chicago Flight Schedule

It’s recommended to check the official Southwest Airlines website or contact their customer support for the most up-to-date information regarding flight schedules.

Southwest BOS to MDW Ticket Prices

Southwest Airlines is known for its affordable ticket prices, providing a cost-effective option for travelers. The ticket prices for the Boston to Chicago route may vary based on factors such as the time of booking, travel dates, and availability. It’s advisable to book your tickets in advance to secure the best deals and discounts offered by Southwest Airlines.

How to Book From BOS to MDW Tickets for Southwest Airlines

Booking a flight from Boston to Chicago with Southwest Airlines is a straightforward process. You can conveniently make your reservation online through the Southwest Airlines website or by using their mobile app.

How to Book From Southwest Boston to Chicago Tickets

The booking process allows you to select your preferred travel dates, choose your seat, and add any additional services or amenities you may require during your flight.

Southwest Airlines Baggage Policy

Southwest Airlines has a generous baggage policy, allowing passengers to bring both checked and carry-on luggage without incurring additional fees. Each passenger can bring one personal item, one carry-on bag, and up to two checked bags, subject to size and weight restrictions. It’s essential to review the specific baggage guidelines on the Southwest Airlines website to ensure compliance and avoid any inconveniences during your journey.

Southwest Rapid Rewards

Southwest Airlines’ frequent flyer program, known as Rapid Rewards, rewards loyal customers with various benefits and privileges. By signing up for Rapid Rewards, you can earn points for each flight you take, which can later be redeemed for free flights, upgrades, and other exciting rewards. Make sure to enroll in the program and start accumulating points to maximize the benefits of your travels with Southwest Airlines.

Airport Information

For passengers flying from Boston to Chicago, Southwest Airlines operates from Boston Logan International Airport (BOS) and arrives at Chicago Midway International Airport (MDW). These airports offer convenient facilities, including dining options, retail stores, and transportation services. It’s advisable to arrive at the airport well in advance to complete check-in procedures and security checks smoothly.

Travel Tips

To make your journey from Boston to Chicago as smooth as possible, consider the following travel tips:

  • Arrive at the airport early to avoid any potential delays.
  • Familiarize yourself with the baggage guidelines to pack accordingly.
  • Keep important travel documents, such as your passport and boarding pass, easily accessible.
  • Stay hydrated throughout the flight by drinking plenty of water.
  • Dress comfortably and wear layers to adapt to changing cabin temperatures.
  • Follow the instructions provided by the flight crew for a safe and pleasant journey.

Customer Reviews

Southwest Airlines has garnered positive reviews from numerous satisfied customers. Passengers appreciate the airline’s friendly and attentive customer service, punctuality, and overall value for money. Many commend Southwest Airlines for its efficient operations and comfortable flights, making it a popular choice for travelers on the Boston to Chicago route.

Safety Measures

In light of the ongoing COVID-19 pandemic, Southwest Airlines has implemented various safety measures to prioritize the well-being of passengers and crew members. These measures include enhanced cleaning protocols, mandatory mask-wearing, social distancing measures, and contactless services. It’s essential to stay updated on the latest safety guidelines provided by Southwest Airlines to ensure a safe and secure journey.


Traveling from Boston to Chicago with Southwest Airlines offers a convenient and enjoyable experience. With multiple daily flights, affordable ticket prices, excellent customer service, and a range of amenities, Southwest Airlines caters to the needs of both business and leisure travelers. Whether you’re visiting family, exploring Windy City’s attractions, or attending business meetings, Southwest Airlines ensures a comfortable and reliable journey from BOS to MDW.


How long does the flight from Boston to Chicago take?

The flight duration from Boston to Chicago may vary depending on factors such as weather conditions and air traffic. However, the average flight time is approximately 3 hours.

Can I bring my own food onboard Southwest Airlines flights?

Yes, you can bring your own food onboard Southwest Airlines flights. However, it’s important to note that Southwest Airlines also provides complimentary snacks and non-alcoholic beverages during the flight.

What are the check-in options available for Southwest Airlines passengers?

Southwest Airlines offers various check-in options, including online check-in through their website or mobile app, self-service kiosks at the airport, and check-in counters staffed by Southwest Airlines personnel.

Are there any extra charges for checked baggage on Southwest Airlines?

No, Southwest Airlines allows passengers to check up to two bags free of charge. However, there are size and weight restrictions that need to be followed. Additional or oversized bags may incur additional fees.

How can I contact Southwest Airlines customer support?

You can contact Southwest Airlines customer support by visiting their official website or calling their dedicated customer service hotline. The contact information can be found on the Southwest Airlines website.

Marquise Snow enjoys traveling a lot. He has traveled to several popular and stunning destinations, such as New York, Bern, Abu Dhabi, and Wellington. He also likes to write his experiences in the form of blogs so that people can find meaningful information about those journeys and places. This can assist people to plan their journeys in better ways.
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