
Popular airlines from Chicago O'Hare International Airport (ORD) to Logan International Airport (BOS)
- JetBlue Airways
JetBlue Airways
- Spirit Airlines
Spirit Airlines
- American Airlines
American Airlines
- Delta
Delta
- United
United
- Plan, book, fly with confidence
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Cheap flights from Chicago (ORD) to Boston (BOS)
Prices were available within the past 7 days and start at CA $71 for one-way flights and CA $124 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.










Find the cheapest month to fly from Chicago (ORD) to Boston (BOS)
September is typically the cheapest month to fly
Graph displaying average flight prices per month
Origin airport | O'Hare Intl. |
Destination airport | Logan Intl. |
Airlines serving | American Airlines, Delta, JetBlue Airways, Spirit Airlines, United |
Roundtrip price | CA $123 |
Distance | 1381 km |
Average flight time | 3 hours 23 mins |
Chicago to Boston Flights
The easy way to book your flights from Chicago to Boston
With Expedia, it’s simple to find and book flights to Boston from Chicago 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, KLM, Qatar Airways, JAL, Icelandair, Emirates, Delta Air Lines, Air New Zealand, United Airlines, Alaska Airlines, Etihad Airways, JetBlue, Avianca, Cathay Pacific, Royal Jordanian, SAS, Hawaiian Airlines, Iberia, ANA, Korean Air, TAP Air Portugal, WestJet, Virgin Atlantic, British Airways nonstop flights to Logan 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 Chicago to Boston today, tomorrow, or this week.
Save dollars with cheap flights from O'Hare Intl., ORD to Logan Intl., BOS
Sort your search results by price to find great deals on your flight from Chicago to Boston—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Boston from Chicago currently is just CA $124 rising to CA $230.
Here are more money-saving tips:
- Fly in October when flight prices are normally at their lowest
- Book about a month to 6 weeks before you travel for the best prices to Boston
- 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 Boston from Chicago
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 Boston with Expedia today.
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Top Routes from Chicago
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Top Routes to Boston
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