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Cheap Flights from Boston to Chicago

Prices were available within the past 7 days and starts at $44 for one-way flights and $88 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Boston to Chicago route information

Origin Airport Logan Intl.
Destination Airport O'Hare Intl.
Airlines Serving American Airlines, Delta, Frontier Airlines, JetBlue Airways, Spirit Airlines, United
Flight Price $87
Distance 863 mi

Providence

$104.80

Worcester

$169.89

Chicago

$194.80

Cheap BOS to ORD Flights

  • How long does the average person visit Chicago?

    Of course, you're not an average person, but if you were, you'd stay around five days.
  • How long does it take to fly from Boston to Chicago?

    This flight takes around two hours and 39 minutes via United Airlines. If you catch the 5:20 AM EST departure, you'll arrive at 6:59 AM CST. Don't forget the one-hour time change.
  • What is the cheapest day to fly?

    The cheapest day to fly from Boston to Chicago is on Tuesday. So, if you want to save a little money on your next holiday look for flights on that day.
  • What is the cheapest day to fly to Chicago?

    Mar 11th has bookings (as of Feb 17th) for as little as $99. That comes in 35% below the average price. Saving now gives you more money in your pocket.
  • What is the cheapest airline flying from Boston to Chicago?

    Spirit Airlines is the leader in keeping costs low for their passengers over the next three months. Bookings are being made at just $87, which is a great deal when compared to the high-end bookings of $454.
  • Which airline has the least delays from Boston to Chicago?

    Booking with Iberia means you will arrive to Chicago around the time you were supposed to. In fact, this timely airline has a 100% average for landing before the plane turns into a pumpkin.
  • From Boston to Chicago, which day is going to have the most flight times?

    The day with the most departure times for this route is Wednesday with 63 options. However, with only 29 flight times, Saturday doesn't offer quite as many options when finding that perfect departure time.

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 BOS to ORD 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 flexbily many prefers to purchase one-way tickets with options to take different airlines. One way ticket to Chicago is $44 now!

Package Disclaimer

*Savings amount equal to 100% when flight + hotel are booked together. Prices based on searches conducted by fellow shoppers within the past 24 hours. There is no guarantee that these prices will be in effect at the time of your search. Vacation package savings are based on comparison to prices on Expedia.com of the same components booked separately. Savings vary based on origin/destination, length of trip, stay dates and travel partners, and aren't available on all packages.