AED280 Cheap Flights from Boston (BOS) to Chicago (ORD)

View AED280 flight on Tue, 13 January 2026Opens in a new window

Popular airlines from Boston to Chicago, IL (ORD-O'Hare Intl.)

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Cheap Flights from Boston to Chicago (BOS-ORD)

Prices were available within the past 7 days and start at AED280 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frequently asked questions

How long does it take to fly from BOS to ORD?
Purchase a ticket with United Airlines and you'll be in the air for about 2 hours and 48 minutes. This leading carrier operates a direct flight that jets off at 9:40AM from BOS and comes in to land at O'Hare Intl. Airport (ORD) at 11:28AM. Expedia has some amazing flight deals, so take a peek at what's on offer on this route today.
Is it cheaper to buy a plane ticket from Logan Intl. Airport (BOS) to ORD last minute?
Booking your flight from Logan Intl. Airport to ORD last minute could save you dollars if you strike it lucky and find a terrific deal. However, fares typically don't come down in price closer to the departure date. If you choose to wait, flights could also be booked up or the best seats taken. If you don't want to risk it, book well ahead of when you want to leave. It's worth noting that some of the best deals can be found up to 12 months in advance. If your preferred carrier hasn't released its airfares yet, check back regularly as deals are constantly updated on Expedia.
What airline has the least delays from Logan Intl. Airport to ORD?
Head off with United Airlines from Logan Intl. Airport (BOS) to O'Hare Airport and touch down at the time printed on your plane ticket. This carrier takes first place on this route, with 81% of flights arriving on time. If your flight is delayed for some reason, the free Expedia App is the best way to stay updated. Our handy app will give you real-time trip updates, from flight delays to gate changes and the carousel number to collect your luggage.
What airports do you fly into for Chicago from Boston?
From Boston, you can reach Chicago via O'Hare Intl. Airport (ORD), Midway Intl. Airport (MDW) and Lewis University Airport (LOT). Research which airport is the most convenient for you before making your decision. If you go with O'Hare Intl. Airport (ORD), it's roughly 26 kilometers northwest of the city center. Use the cash you save when booking your airfare with Expedia to tour the city's top sights, such as Wrigley Field and Millennium Park.
What are the most popular departure times for flights from Logan Intl. Airport (BOS) to O'Hare Airport?
The most popular departure times for journeys from BOS to O'Hare Intl. Airport (ORD) fall between 9:00 AM - 10:00 AM on United Airlines. Our advice is to jet off in the morning. The earlier you travel, the better your chances of a delay-free flight with lighter air traffic in the sky.
Can I change the date of my flight from Logan Intl. Airport to O'Hare Intl. Airport (ORD)?
It's a snap to make amendments to your BOS to O'Hare Intl. Airport (ORD) journey yourself. Just log in to the Expedia Trips portal and click on "change flight." Look around for new flights and secure the one that works best. You'll see an estimate of applicable flight change costs. You can also find your way to our Customer Service portal to chat to our Virtual Agent and get answers to your questions.

Travel information

Origin airport
Logan Intl.
Destination airport
O'Hare Intl.
Distance
1381 km
Average flight time
2 hours 4 mins

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 AED280 now!

Boston to Chicago Flights

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