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Cheap BOS to ORD Flights

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

Boston to Chicago route information

Origin Airport Logan Intl.
Destination Airport O'Hare Intl.
Airlines Serving American Airlines, Delta, JetBlue Airways, Spirit Airlines, United
Flight Price $91
Distance 863 mi

New Bedford










Cheap BOS to ORD Flights

  • What is the cheapest day to fly to Chicago?

    As of Sep 16th, the best day for booking to Chicago (ORD) is Sep 17th. A ticket will cost you $103, which is 36% less than the average price to book the same route.
  • How many flights are there per day from Boston to Chicago?

    The number of flight times varies by day, but on average, BOS to ORD sees 36 different choices. Compared to the average route departing the United States with nine flight times, you'll have more options than most.
  • What is the cheapest airline flying from Boston to Chicago?

    Spirit Airlines is the leader in keeping costs down for their passengers over the next three months. Fares are being booked at just $103 and, when compared to the more expensive bookings of $517, it's a terrific deal.
  • How long do most people stay in Chicago?

    Of course, you are not most people, but if you were, you'd stay roughly four days.
  • How much is a plane ticket to Chicago (ORD) from Boston (BOS)?

    Cost can range from $103 to $517, prices for BOS to ORD change less than most routes in the United States. However, usually the sooner you book, the better the price.
  • How long is the flight from BOS to ORD?

    This direct flight will whoosh you away to your destination in two hours and 47 minutes via United Airlines. If you catch the 2:50 PM EDT departure, you'll arrive at 4:37 PM CDT. Giving you plenty of time to freshen up or grab a quick lunch before your next rendezvous (remember, there is a time change of one hour).
  • What day has the most flight time options?

    The day with the most departure times for this route is Sunday with 40 options. Saturday currently offers the least amount of flight times with 30 options.

Boston to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Boston to Chicago will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at, we’ll pair you up with BOS to ORD flights that won’t make your bank account wince. Ready to temporarily leave behind Boston for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to ORD with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.