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Selected fares from Boston to Chicago

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

Route Information for Flights from Boston to Chicago

Origin Airport IATA Code MHT
Destination Airport IATA Code ORD
Flight Price $79
Distance 1,345 km

Boston (BOS) to Chicago (CHI)

Whether you're traveling for business or pleasure, you're going to want a great deal on a flight to Chicago. Because when you eventually land, you have a city that is waiting to be explored, and that extra cash in your pocket can take your trip from "meh" to amazing. You're on the right page to grab an awesome deal on your next flight from Boston. Whether you label yourself an airline aficionado or you're new to the jet-setting scene, read on to see how to book a too-good-to-be-true flight.

How do I get the best price on my flight from BOS to CHI?

We've been doing this for years, which means getting that great deal on a Chicago flight is easy-peasy. You'll make spending less look so very good 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. Most people opt to depart at the beginning or end of the week.
  • Thursday and Saturday—Get a head start on that Friday crowd. This also works on your return flight. Shorten your vacay by a day and increase your savings.
  • Monday through Thursday—If you're flying internationally, deals are often available when departing these days.

What's the Saturday night stay rule?

Staying the weekend at your destination, like Chicago, usually means lower airfare since most people fly during this time. Good thing to tell your boss if you have a business trip -- wink-wink.

Can you save while traveling during the off-peak season?

Have good weather, will travel. Summertime is when Europe, Hawaii, and Alaska are at their most popular. During spring, New Orleans, Florida, and California open their arms to tourists. Winter is prime for Mexico and the Caribbean because of its warm weather, as well as ski and snowboard destinations like the Colorado Rockies. Who doesn't love some good fall foliage? The Pacific Northwest, Northern California, and New England are popular this time of the year. 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.

Is that the lowest price?

Airlines change their rates frequently. If a price you want pops up, then pick it! Unsurprisingly, you're not the only vacation-hungry person longing for a great rate on a flight from Boston to Chicago. You may lose your chance to dial in the time and the flight you wanted.

Are there any other ways to save?

The Hotwire Hot Rate is what makes us one of the best bargains out there. You can get one of the best rates on a flight from Boston (BOS) to Chicago (CHI). You won't know the time and airline until after you book, but if you are not on a set schedule, you can save big on your flight.

Book your Boston to Chicago flight today

We're here to help you save some money on your ticket from Boston to Chicago. Use our guide to help you land that unreal deal. For traveler that likes to take it as it comes, and save while doing it, go for the Hotwire Hot Rate. You'll get your flight and have more money in your wallet to do Chicago up right. So say "So long" to Boston and "What's up?" to Chicago.

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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.