Book Cheap Flight Tickets from Chicago (CHI) to Boston (BOS)

Grab your cheap flights from Chicago to Boston with Crystal Travel

Whether you're visiting a loved one, planning a vacation, or traveling for business, flying to Boston from Chicago is guaranteed to be an enjoyable experience. The magnificent and lovely Boston is a sight to see. However, browsing the many airline websites and choosing cheap flights from Chicago to Boston within budget might be a challenging endeavor.

Crystal Travel is ready to assist you in finding flight tickets that are within your budget. We offer some of the finest prices on flights that will fit your schedule and price range, whether you want to travel one-way, non-stop, or round trip. So, what are you waiting out now for? Book your low-cost flight tickets from Chicago to Boston.

About Chicago

A flourishing hub of international trade and commerce, and a destination for individuals of many nationalities and backgrounds seeking the American dream. A place, most renowned for its hotdogs, jazz music, architecture, some insane sports fans, and delicious Chicago-style pizzas.

About Boston

Boston is one of the most historically rich cities in America. The legends of the Midnight Ride and its tea parties are reason enough to visit this location. Boston is an interesting destination to visit because of its famed baked beans and its status as a major commercial center.

Cheap Flights from Chicago to Boston

Click on the Origin Airport of your choice to unlock various flight deals

FAQs on Chicago to Boston Flights

1. Which airlines fly directly from Chicago to Boston?

Below are the major airlines that fly non-stop from Chicago to Boston—

  • Southwest
  • American Airlines
  • JetBlue
  • Delta
  • United Airlines
  • Spirit Airlines
2. I’m booking a non-stop/direct flight to Boston from Chicago. Which airport do I choose?

When departing from Chicago, you can choose from one of the following airports:

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

Choose amongst these two airports depending upon your destination, travel cost, and time is taken. In Boston, you will be landing at Boston Logan Intl. Airport.

3. What is the duration of the flight between CHI and BOS?
A nonstop trip from Chicago to Boston normally takes 2h 50m. The trip covers a total distance of 851 miles. Delta and Southwest Airlines are known to be serving the route in the least time by covering a distance around 5 minutes early.
4. Which airline has the least delayed flights from Chicago to Boston?
Delta Air Lines has the fewest delayed flights between Chicago and Boston, according to statistics accessible until April 2022, followed by Southwest, United, and American Airlines. Except for weather and technical concerns, these flights are consistently on schedule.
5. Which is the cheapest day of the week to fly from Chicago to Boston?
On your return trip to Chicago, consider flying on a Tuesday and avoiding Thursdays. It is generally cheaper to fly to Boston on a Saturday and more expensive on a Monday.
6. Do I need to pay any fees or charges for canceling my flight from ORD/MDW to BOS?
For flight adjustments or cancellations, most airlines charge a service fee. These days customers can cancel their flights online at any time, according to some airline policies. Please contact our customer care team or visit the airline's website for further information.
7. Do airlines offer sleeping areas to passengers traveling from Chicago to Boston?
If you are flying from Chicago then O'Hare International Airport has private lounges to sleep in and rest. Boston airport on the other hand has the resting chairs but no lounges to sleep.
8. Am I allowed to carry food/eatables on my flight to Boston?
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 Chicago to Boston?
Each checked bag must have a maximum linear size of 158 cm (62 inches) and a maximum weight of 23 kg, according to US travel restrictions (50 pounds). As a consequence, it's advisable to plan ahead of time and confirm your luggage dimensions with the airline for your Chicago to BOS journey.
10. I lost my baggage during my flight to Boston from Chicago, 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. You can check the airline and government policies or contact travel experts for more information.

11. What are the latest offers available with Crystal Travel on flights to Boston?
Crystal Travel readily has low-cost flights to Boston. You can discover some of the most major deals for your vacation in just a few clicks by using our vast search engine. Add your travel destinations. Then, to locate the most recent deals, use search. If you're still undecided, contact our travel specialists, who will provide you with the most recent discounts.
Search Offers Navigation

Get a great deal on your next holiday