CA $70 Cheap Flights from Chicago (ORD) to Boston (BOS)

View CA $70 flight on Tue, Apr. 8, 2025Opens in a new window

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

Prices were available within the past 7 days and start at CA $70 for one-way flights and CA $139 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sun., May 25 - Tue., Jun. 10
ORD
Chicago
BOS
Boston
CA $139 Roundtrip, found 3 days ago
CA $139
Roundtrip
found 3 days ago
Select Delta flight, departing Sun., May 25 from Chicago to Boston, returning Tue., Jun. 10, priced at CA $139 found 3 days ago
American Airlines
Fri., Apr. 4 - Mon., Apr. 7
ORD
Chicago
BOS
Boston
CA $139 Roundtrip, found 6 days ago
CA $139
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri., Apr. 4 from Chicago to Boston, returning Mon., Apr. 7, priced at CA $139 found 6 days ago
JetBlue Airways
Thu., Sep. 4 - Wed., Sep. 10
ORD
Chicago
BOS
Boston
CA $139 Roundtrip, found 12 hours ago
CA $139
Roundtrip
found 12 hours ago
Select JetBlue Airways flight, departing Thu., Sep. 4 from Chicago to Boston, returning Wed., Sep. 10, priced at CA $139 found 12 hours ago
Delta
Tue., Aug. 5 - Tue., Aug. 26
ORD
Chicago
BOS
Boston
CA $140 Roundtrip, found 21 hours ago
CA $140
Roundtrip
found 21 hours ago
Select Delta flight, departing Tue., Aug. 5 from Chicago to Boston, returning Tue., Aug. 26, priced at CA $140 found 21 hours ago
Delta
Thu., Aug. 7 - Mon., Aug. 11
ORD
Chicago
BOS
Boston
CA $152 Roundtrip, found 5 days ago
CA $152
Roundtrip
found 5 days ago
Select Delta flight, departing Thu., Aug. 7 from Chicago to Boston, returning Mon., Aug. 11, priced at CA $152 found 5 days ago
JetBlue Airways
Thu., Apr. 3 - Mon., Apr. 7
ORD
Chicago
BOS
Boston
CA $153 Roundtrip, found 15 hours ago
CA $153
Roundtrip
found 15 hours ago
Select JetBlue Airways flight, departing Thu., Apr. 3 from Chicago to Boston, returning Mon., Apr. 7, priced at CA $153 found 15 hours ago
Delta
Thu., Apr. 3 - Mon., Apr. 7
ORD
Chicago
BOS
Boston
CA $154 Roundtrip, found 15 hours ago
CA $154
Roundtrip
found 15 hours ago
Select Delta flight, departing Thu., Apr. 3 from Chicago to Boston, returning Mon., Apr. 7, priced at CA $154 found 15 hours ago
Delta
Thu., Apr. 3 - Mon., Apr. 7
ORD
Chicago
BOS
Boston
CA $155 Roundtrip, found 15 hours ago
CA $155
Roundtrip
found 15 hours ago
Select Delta flight, departing Thu., Apr. 3 from Chicago to Boston, returning Mon., Apr. 7, priced at CA $155 found 15 hours ago
United
Fri., Apr. 4 - Mon., Apr. 7
ORD
Chicago
BOS
Boston
CA $191 Roundtrip, found 6 days ago
CA $191
Roundtrip
found 6 days ago
Select United flight, departing Fri., Apr. 4 from Chicago to Boston, returning Mon., Apr. 7, priced at CA $191 found 6 days ago
Spirit Airlines
Wed., Jun. 25 - Mon., Jun. 30
ORD
Chicago
BOS
Boston
CA $194 Roundtrip, found 3 days ago
CA $194
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed., Jun. 25 from Chicago to Boston, returning Mon., Jun. 30, priced at CA $194 found 3 days ago
Flight from Chicago to Boston (ORD - BOS) route information
Origin airport
O'Hare Intl.
Destination airport
Logan Intl.
Airlines serving
American Airlines, Delta, JetBlue Airways, Spirit Airlines, United
Roundtrip price
CA $138
Distance
1381 km

Chicago to Boston Flights

Ready for an adventure? Thought so! Prepare to see the sights when you book your trip from Chicago to Boston with Expedia.ca. Whether you’re visiting for business or pleasure, we know how important it is to bring home travel stories. Maybe your tales will include the best dinner of your life, or the weirdest street art you saw in the city, or the concert that turned you into a fan of a new band. Whatever it is, your new favourite anecdote is right around the corner. Book your trip from ORD to BOS and begin your journey!

Getting a cheap deal on your trip sets the tone for the perfect holiday. And with Expedia.ca, you know you can travel from Chicago to Boston on the cheap, with enough money left over for a stellar time in the city. That could mean more tours with the kids, more concerts with the spouse, more dessert amongst co-workers, or even front row seats to a sports game if you’re travelling solo. It’s your holiday! Make it great.

Travelling shouldn’t cost an arm and a leg before you even get to relax on the plane’s armrests. Count on Expedia.ca to get you the best discounts on flights from ORD to BOS. And remember this: You can also save big when you bundle. Add a hotel or car rental deal to your flight and witness those savings add up. Hey, more money for more souvenirs, right? Right! Pack your bags and we’ll see you on the route.

Combine your Boston flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights from with Expedia Canada. Use us as your top travel destination and have the confidence that you’re getting a bargain!

Frequently asked questions

How much is a flight from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS)?
Start packing your suitcase, because round-trip flights from ORD to Logan Intl. Airport (BOS) start from CA $139. That’s based on airfares listed within the last 7 days on Expedia for flights departing within the next year. Prices can change quickly, so book now to score the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from O'Hare Airport to BOS?
Most flights can be canceled online, but every air carrier has different terms and conditions. If you do need to cancel your flight, check out our Customer Service Portal and follow the instructions.
How do I find cheap flights from ORD to Logan Intl. Airport 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 O’Hare Airport to Logan Intl. Airport flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from O'Hare Airport to Logan Intl. Airport?
That new movie you’ve been desperate to see will just have to wait — the flight distance between O’Hare Airport (ORD) and BOS (BOS) is only 1,400 kilometers. The captain will be asking you to put your seat upright for landing before you know it.
Which airlines fly direct from ORD to Logan Intl. Airport (BOS)?
It’s easy to fly directly from O’Hare Intl. Airport (ORD) to Logan Intl. Airport. Here are some of the top carriers that offer nonstop services on this route:

  • American Airlines - (AA) with 225 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 O'Hare Intl. Airport (ORD) to Logan Intl. Airport flight tickets cheaper when they're purchased at the last minute?
It is possible to score an awesome last-minute deal from ORD to BOS, but there’s no guarantee. As many airlines release seats up to a year in advance, it’s worth keeping an eye on fares early and being ready to book when you see a good bargain. Expedia compares carrier prices and updates flight deals regularly, so you can be certain you’re always seeing the latest offers.
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