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Cheap ORD to BOS Flights

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

Chicago to Boston route information

Origin Airport O'Hare Intl.
Destination Airport Logan Intl.
Airlines Serving American Airlines, Delta, JetBlue Airways, Spirit Airlines, United
Flight Price $113
Distance 863 mi



New Bedford








Cheap ORD to BOS Flights

  • Which airline has the least delays from Chicago to Boston?

    Booking with Frontier Airlines means you will arrive to Boston pretty close to the time your ticket states. In fact, this timely airline has a 100% average for landing before the plane turns into a pumpkin. It never hurts to be prepared. If you should choose this airline, be sure to track the flight status to stay on top of the departure time.
  • What is the cheapest airline flying from Chicago to Boston?

    Spirit Airlines strives to keep prices low for their passengers over the next three months. Fares are being booked at just $103 and, when compared to the pricier bookings of $727, it's quite a deal.
  • What day of the week has the most flight time options?

    With 41 total flight time options, Sunday provides the most flexibility from ORD to BOS. Saturday currently offers the fewest number of flight times with only 34 options.
  • What is the cheapest day to fly to Boston?

    If you are needing to save cash, look at Oct 9th. As of Sep 16th, it's showing the cheapest ticket at $103. That is 34% below the average price for this route, so you can spend that extra money on some souvenirs while in Boston.
  • How many flights are there per day from Chicago to Boston?

    Depending on the day of the week, the number of flight times will change, but on average there are 37. You'll have more choices on this route than most other routes departing the United States.
  • How much time do people spend in Boston?

    The average time spent hanging out in Boston by passengers from Chicago is four days.
  • What is the cheapest day to fly?

    The cheapest day to fly from Chicago to Boston is on Tuesday. So, if you want to save a bit of money on your next holiday look for flights on Tuesday.

Chicago to Boston 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 Chicago to Boston 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 Boston.

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 ORD to BOS flights that won’t make your bank account wince. Ready to temporarily leave behind Chicago 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 BOS 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.

Sep 14, 2019

TSA agent could have been more friendly

Sep 6, 2019

First time on Jet Blue. My new favorite airline.

Aug 28, 2019

Good experience!

Aug 28, 2019

The attitudes of the captain and crew made me feel at ease- informative, happy to be there, great timing with snacks and garbage bags. Trip was fast and smooth, I was really happy because I’m very afraid to fly. Thank you

Aug 25, 2019

baggage was delivered quite late

Aug 18, 2019

Need to add Delta entertainment for each seat.

Aug 17, 2019

Check in staff went ten extra miles to get us on an earlier flight when our original flight was delayed. So much better than United who quite frankly couldn't give a damn.

Aug 15, 2019

Leaky air conditioner at my seat , 5D

Aug 14, 2019

Would be great to select aisle seats in the same raw you are assigned for free. In order not to bother people if you wanna use facilities. Thanks

Aug 10, 2019

Great flight attendant