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Selected fares from Chicago to Boston

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Route Information for Flights from Chicago to Boston

Origin Airport IATA Code ORD
Destination Airport IATA Code BOS
Flight Price $127
Distance 1,381 km

Chicago (CHI) to Boston (BOS)

What?! A trip to Boston! Well, looks like you'll need a flight from Chicago pretty soon. We suppose you could ride a scooter for most of it, but you probably are on a bit of a schedule. Luckily, you found us. Hotwire can get you a great deal on your ticket from CHI to BOS.

How can you get a great rate on tickets from Chicago to Boston?

We've been in the game a long time, which means getting that great deal on a Boston flight is easy-peasy. You can pocket that extra cash for more than just getting from point A to point B with a little know-how.

What is the best day of the week to book a flight?

With the right attitude and flexibility, you can fly for less. Below are the cheapest days to fly:

  • Tuesday and Wednesday—You know how most stores are not crowded midweek? Same thing here. So, get on while the getting is good.
  • Thursday and Saturday—Get a head start on that Friday crowd. This also works on your return flight. Shorten your holiday by a day and increase your savings.
  • Monday through Thursday—If you're flying internationally, deals are often available when departing these days.

Why are flights cheaper if you stay over the weekend?

If you stay through the weekend, generally that return ticket to CHI can be cheaper since you'll be leaving earlier in the week. All those business travelers have less elastic itineraries, so that means savings for you. Good thing to tell your boss if you have a business trip -- wink-wink.

What are shoulder seasons?

It's all about going to a place when its weather is at its best. Summertime is when Europe, Hawaii, and Alaska are at their most popular. Popular Spring Break destinations are New Orleans, California, and Florida. Winter is prime for Mexico and the Caribbean because of its warm weather, as well as ski and snowboard destinations like the Colorado Rockies. In the autumn, Northern California, the Pacific Northwest, and New England draw visitors. If you can plan your trip around these peak seasons, you'll not only save money, but you'll typically avoid the crowds. Win-win in our books.

Jump on that great rate

Airlines change their rates seemingly by the minute. If you discover the price you like, then get it. There are a lot of others that are seeking a great deal on a flight from Chicago to Boston. You may miss out on your chance to dial in the time and the flight you wanted.

How else can I save on my flight from Chicago to Boston?

We think the Hotwire Hot Rate is one of the best deals out there, although we may be slightly biased. You'll get one of our best rates on a flight from Chicago (CHI) to Boston (BOS). After your purchase, you'll get the time and name of the airline, but if you are not on a set schedule, you can save big on your flight.

Book your Chicago to Boston flight today

At Hotwire we'll do our best to help you save on your ticket from Chicago to Boston. Use our guide to get you that crazy good deal. For those risk-takers that don't like to be too risky, go for the Hotwire Hot Rate. You'll get your flight and have more money in your pocket to do Boston up right. So say "So long" to Chicago and "What's up?" to Boston.

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^Savings based on all package bookings with Flight + Hotel made on Hotwire.com from January 1, 2018 to December 31, 2018 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.