Book Cheap Flight Tickets from Boston (BOS) to Chicago (CHI)
Grab the cheap flight deals on your next flight with Crystal Travel

No matter how many flights you book, whether it's your first or 100th, you need to choose an airline that is within your budget and lands at your destination quickly. As well as being affordable, security is usually a major concern for travelers, which is why we offer cheap flights from Boston to Chicago. 

Crystal Travel's goal is to offer its customers low-cost flights from the best airlines in the industry. The dynamic search engine on our website makes it easy for users to locate the best deals from their favorite airlines, regardless of whether they travel in economy or business class. As an IATA and ASTA-protected company, we are able to provide a safe and secure option for booking flight tickets. 

About Boston

Boston is best known for its famed baked beans, Fenway Park, The Boston Marathon, and, of course, the bar from Cheers, but scratch the surface and you'll discover a startling richness of things that make Boston one of the finest cities in America—and the globe. Loved for its beans, Boston is also known as Bean town. However, you can also explore some mouth-watering seafood there. 

About Chicago

It is a cultural destination with several museums, tourist sites, nature centers, and bustling nightlife. Visitors from all over the world come to Chicago's yearly food festivals to experience the city's delectable cuisine.

Cheap Flights from Boston to Chicago

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FAQs on Boston to Chicago Flights
1. Which airlines fly directly from Boston to Chicago?

Airlines that fly directly from Boston to Chicago are:

  • American Airlines
  • United Airlines 
  • Delta Airlines
  • Southwest Airlines

Crystal Travel offers the finest deals on these popular airlines, allowing you to select what best fits your budget.

2. I’m booking a non-stop/direct flight to Chicago from Boston. Which airport do I choose?

Chicago is served by two airports, where all the flights from Denver can land. The airports are:

  • O'Hare International Airport (ORD)
  • Chicago Midway International Airport (MDW)


You can choose amongst the airports at your convenience. All the flights will depart from Boston Logan International Airport (BOS)  the only international airport in Boston

3. What is the duration of the flight between BOS to ORD?
O'Hare International Airport is typically two hours and forty minutes from Boston by nonstop flight. It travels over a distance of 851 miles.
4. Which airline has the least delayed flights from Boston to Chicago?
Delays on flights are caused by a variety of circumstances, including technical issues and weather conditions. American Airlines and Frontier, on the other hand, offer the least delayed flights from Orlando to Chicago.
5. Which is the cheapest day of the week to fly from Boston to Chicago?
If you want to obtain the greatest rates on flights from Boston to Chicago, fly on a Saturday and avoid flying on Mondays. If you're returning to Boston, the best days to book are Tuesdays, while Sundays are the most costly.
6. Do I need to pay any fees or charges for canceling my flight from BOS to ORD?
Many airlines have changed their cancellation rules after the covid breakout. You can contact our customer care assistance for more information on this or visit the airline's official website since each airline has its own cancellation policy.
7. Do airlines offer sleeping areas to passengers traveling from Boston to Chicago?
Both Boston and Chicago airports have comfortable armrest chairs, but if you want to get pampered before boarding a trip from Boston, go to BeRelax, which offers manicure, waxing, and facial care services to help you rest before your travels.
8. Am I allowed to carry food/eatables on my flight to Chicago?
As per the TSA rules, you are allowed to carry food/eatables in your carry-on or checked baggage as long as it is solid and well packed. Passengers are not allowed to carry liquid, semi-liquid, and gel items.
9. What is the baggage allowance on a flight from Boston to Chicago?
Most airlines allow 20kg or 23kg of checked luggage per passenger. On average, checked baggage measurements are 90cm x 75cm x 43cm. Hand luggage transported into the cabin should not exceed 7kg, and cabin baggage dimensions should be 23cm x 36cm x 56cm.
10. I lost my baggage during my flight to Chicago from Boston, how can I recover it?

In case you lost your baggage during a flight, here are a few steps you can take to recover it.

  • Contact the airlines immediately. Airlines are responsible for any lost, damaged, or delayed baggage. They have a system to track and identify bags' location.
  • Request for delivery to your address or accommodation till it's found.
  • Request for the baggage fee reimbursement
  • Keep all the receipts of incidental expenses.


Most airlines take 24 hours to 5 days to declare that the baggage is lost. In case your baggage is lost, airlines will compensate you for your bag and its content. For more information, you can check the airline and government policies or contact travel experts.

11. What are the latest offers available with Crystal Travel on flights to Chicago?
Crystal Travel has a number of deals on flights to Chicago. Using our extensive search engine, you may find some of the most recent vacation bargains in only a few clicks. To remain up to date on the newest airline tickets and specials, sign up for our newsletter and follow us on social media.
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