Cheap Flights from Boston (BOS) to Chicago (DPA)

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Frequently asked questions

Is it cheaper to buy a plane ticket from Logan Intl. Airport (BOS) to Dupage Airport (DPA) last minute?
Being the spontaneous type is an awesome way to travel, but it isn't always the wisest method to find a bargain airfare. It's better to book your Logan Intl. Airport (BOS) to DPA trip in advance rather than waiting till the last minute. Based on flight pricing and demand studies in 2022, we have found that the best time to book domestic flights is between 28 – 35 days ahead of the departure date, and international flights three to four months in advance. Save all that spontaneity for when you reach DPA!
What airports do you fly into for Chicago from Boston?
With Dupage Airport (DPA), O'Hare Intl. Airport (ORD) and Lewis University Airport (LOT) to select from, connecting from Boston to Chicago is easy. The city's main terminal, Dupage Airport (DPA), is approximately 48 kilometers west of the center. Along with ticket prices, consider factors like the ease of getting from the airport and the distance to your hotel when deciding where to fly into. Get your Chicago vacation off to an awesome start by visiting Wrigley Field and Millennium Park.
Can I change the date of my flight from Logan Intl. Airport (BOS) to DuPage Airport?
It's so easy to make amendments to your Logan Intl. Airport to Dupage Airport (DPA) trip yourself. Simply go to the Expedia Trips portal and hit "change flight." Look for new flights and choose the one that works best with your plans. You'll see an estimate of applicable flight change costs. You can also find your way to our Customer Service portal to connect with our Virtual Agent and quickly get answers to all your questions.

Travel information

Travel information

Origin airport
Logan Intl.
Destination airport
Dupage
Distance
1411 km

Book with confidence

Book with confidence

Boston to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Boston to Chicago offer the perfect respite. Not only does exploring Chicago provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Boston to Chicago may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from to today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Chicago are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Chicago more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Chicago is now!

Boston to Chicago Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia