CA $60 Cheap Flights from Boston (BOS) to Chicago (ORD)

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Cheap flights from Boston (BOS) to Chicago (ORD)

Prices were available within the past 7 days and start at CA $60 for one-way flights and CA $129 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Spirit Airlines
JetBlue Airways
Spirit Airlines
Spirit Airlines
JetBlue Airways
American Airlines
Delta
JetBlue Airways
JetBlue Airways
Flight from Boston to Chicago (BOS - ORD) route information
Origin airport
Logan Intl.
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, JetBlue Airways, Spirit Airlines, United
Roundtrip price
CA $128
Distance
1381 km

Boston to Chicago Flights

The easy way to book your flights from Boston to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from Boston whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are American Airlines, Qatar Airways, JAL, Delta Air Lines, Air New Zealand, United Airlines, Alaska Airlines, JetBlue, Avianca, Cathay Pacific, Royal Jordanian, SAS, Iberia, Hawaiian Airlines, Korean Air, ANA, TAP Air Portugal, Virgin Atlantic, British Airways nonstop flights to O'Hare Intl., too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Boston to Chicago today, tomorrow, or this week.  

 

Save dollars with cheap flights from Logan Intl., BOS to O'Hare Intl., ORD 

Sort your search results by price to find great deals on your flight from Boston to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Boston currently is just CA $129 rising to CA $162.  

Here are more money-saving tips: 

  • Fly in November when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Chicago  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Chicago from Boston 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today.

Frequently asked questions

How much is a flight from Logan Intl. Airport to ORD?
If you’re planning on traveling from BOS to O’Hare Airport, round-trip flights start from CA $129. This price is based on airfares advertised within the last 7 days on Expedia for flights departing within the next year, so don’t hang about. Book now and save yourself both money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Logan Intl. Airport (BOS) to ORD?
The majority of flights can be conveniently canceled online, but whether or not you incur a fee varies between airlines. If you do have to cancel your trip, follow the easy instructions in the Customer Service Portal.
How do I find cheap flights from BOS to O'Hare Intl. Airport (ORD) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you’re searching for Logan Intl. Airport to O’Hare Airport flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from BOS to O'Hare Intl. Airport (ORD)?
Forget about a movie marathon on this flight — it’s only 1,400 kilometers from Boston to Chicago. Sit down, buckle up and you’ll be touching down before long.
Which airlines fly direct from Logan Intl. Airport to ORD?
It’s a breeze to fly directly from Logan Intl. Airport to ORD. Below are some of the top carriers that operate nonstop services on this route:

  • American Airlines - (AA) with 230 monthly flights
  • United Airlines - (UA) with 178 monthly flights
  • Delta Air Lines - (DL) with 139 monthly flights
  • JetBlue Airways - (B6) with 30 monthly flights

Are Logan Intl. Airport to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute?
It is possible to get great last-minute deals from BOS to O’Hare Airport, but it’s also possible to miss out entirely! As many airlines publish prices up to a year in advance, it’s worth keeping an eye on fares early and being ready to pounce when you spot a good bargain. Expedia compares air carrier prices and updates flight deals frequently, so you can rest easy knowing you’re always getting the latest offers.
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