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Fares from $25 One Way, $50 Round Trip from Chicago to Boston

Prices starting at $50 for return flights and $25 for one-way flights to Boston were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

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More About Flying To Boston from Chicago

Route Information for Flights from Chicago to Boston

Origin Airport IATA CodeCHI
Destination Airport IATA CodeBOS
Distance863 mi
Direct Flight AirlinesIcelandair, JetBlue Airways, SAS, Hawaiian Airlines, ANA, TAP Air Portugal, Air New Zealand, United Airlines
Earliest Flight Arrival4:36PM UTC
Latest Flight Arrival1:35AM UTC

Flights Review

Mar 16, 2020

TSA ARE VERY RUDE. for a person that has flown twice since 9/11, 1st time tsa took my lucky coins, this time they were just plain rude! I can't read minds and you are scared to move wrong and if you don't. Over fast enough, they are just plain hateful.

Feb 28, 2020

Our attendants on this flight were so kind and helpful! They were very friendly and personable!

Feb 23, 2020

Great flight with Delta

Feb 21, 2020

Hated the extra cost of buying seats to guarantee that we sat together. Not sure I would do this again. The value isn’t there.

Jan 7, 2020

I liked that I was allowed early boarding with my 4 year old. Not every airline allows that. Delta is great!

Dec 23, 2019

Wifi would not work and USB port was broke

Dec 22, 2019

Seats are so tight and small. But you get what you pay for.

Dec 16, 2019

Nice trip.

Dec 14, 2019

First time on Jet Blue and it was a good experience

Dec 8, 2019

Great airline. I wish they had more routes.

Orbitz is the best online spot to find cheap tickets to put the wind beneath your wings for flights from Chicago to Boston you'll have a few extra bucks in your back pocket when you land in Beantown.

The Windy City offers two options for budget fares for your Chicago to Boston flight, depending on your location and personal tastes. O'Hare International Airport (ORD) is in the northwest corner, 17 miles from the downtown loop. Midway International Airport (MDW) is on the southwest side, eight miles from the loop. Budget-conscious planners who opt for O'Hare will find that the bustling airport, the world's second largest, is a hub for United Airlines and American Airlines and that the smaller Midway is a hub for Southwest Airlines. Your Chicago to Boston flight could be on any of the major airlines, because they all serve Massachusetts' capital city with direct flights. O'Hare offers the best in airport accommodations with a handful of lounges, classic American and international food, and a lot of specialty shops to procure a one-of-a-kind souvenir.

Even though the two-hour nonstop Chicago to Boston flight is a domestic route, you will step into a historic city known as the Athens of America when you land at Logan International Airport (BOS). Aviation.com dubbed Logan the "Easiest Airport to Get To" in 2007 because of its transportation options, including rental cars, cabs, vans, limos and several options from the Massachusetts Bay Transportation Authority (MBTA) like the Blue line train, the Silver line train, and the ferry. That means it is easy to enjoy your flight from Chicago to Boston without having to think about any other hassles, whether you're traveling the three miles to downtown or you're a budget planner who plotted tours of the City on a Hill when you booked tickets. If you're coming from Chicago, the weather in Boston will be nothing new, but chances are you'll want to book your flight from Chicago to Boston in the summer.

Flights from Chicago to Boston - Frequently Asked Questions

Are there non-stop flights from Chicago to Boston?

Yes, you can book direct flights from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.). What's more, there are 5 airlines to choose from. Pretty cool, huh? See which of these well-known carriers works the best for you:

  • United Airlines
  • American Airlines
  • JetBlue Airways
  • Delta Air Lines
  • Spirit Airlines
What is the shortest flight from Chicago to Boston?

If conditions are good and everything goes to plan, you could be flying into Boston, MA (BOS-Logan Intl.) from Chicago, IL (ORD-O'Hare Intl.) in just 2 hours and 8 minutes. With such a short flight time, think about taking carry-on luggage only.

What airlines fly from Chicago (and vicinity) to Boston (and vicinity) most frequently?

With a good variety of airlines flying between Chicago, IL Airport (ORD-OHare Intl.) and Boston, MA Airport (BOS-Logan Intl.), you'll have your choice of fantastic deals. The carriers operating on this route the most frequently are: United Airlines - (UA) with 201 flights every month American Airlines - (AA) with 165 flights every month JetBlue - (B6) with 108 flights every month Delta - (DL) with 92 flights every month

If I am not able to travel due to COVID-19, can I cancel my flight to Boston?

We get that traveling right now has its challenges, so it's good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Boston have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you'll quickly see what options are available. Our Customer Service Portal is the place to go for more information.

Are there flights to Boston with flexible change policies?

In most cases you'll have the option to reschedule your flight to Boston without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the "no change fees" filter and book with confidence.

What is the cheapest day of the week to fly?

Consider flying out early in the week to save on your airfare. Orbitz data from 2019 shows that Tuesday is the cheapest day to depart, followed by Monday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.

What is the cheapest month to fly?

We won't keep you guessing, according to Orbitz data the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a fresh start to the new year. Be aware that the most expensive time to fly isn't the height of summer, as most people assume, but the festive month of December.

How can I save money on flights?

To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you'll generally get a much better deal. Those who tried this on Orbitz in 2019 saved over 50% on their airfares. Get mixing and matching today!

*According to flight demand on Orbitz.com from January to December 2019. Savings are subject to change based on departure location, date and destination.

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.