CA $85 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 $85 for one-way flights and CA $172 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Wed., Feb. 5 - Wed., Feb. 12
BOS
Boston
ORD
Chicago
CA $172 Roundtrip, found 2 days ago
CA $172
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed., Feb. 5 from Boston to Chicago, returning Wed., Feb. 12, priced at CA $172 found 2 days ago
Spirit Airlines
Wed., Feb. 5 - Wed., Feb. 12
BOS
Boston
ORD
Chicago
CA $199 Roundtrip, found 2 days ago
CA $199
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed., Feb. 5 from Boston to Chicago, returning Wed., Feb. 12, priced at CA $199 found 2 days ago
Spirit Airlines
Tue., Feb. 25 - Thu., Feb. 27
BOS
Boston
ORD
Chicago
CA $211 Roundtrip, found 1 day ago
CA $211
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue., Feb. 25 from Boston to Chicago, returning Thu., Feb. 27, priced at CA $211 found 1 day ago
Spirit Airlines
Wed., Feb. 26 - Wed., Mar. 5
BOS
Boston
ORD
Chicago
CA $211 Roundtrip, found 3 days ago
CA $211
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed., Feb. 26 from Boston to Chicago, returning Wed., Mar. 5, priced at CA $211 found 3 days ago
JetBlue Airways
Thu., Jan. 16 - Wed., Jan. 22
BOS
Boston
ORD
Chicago
CA $213 Roundtrip, found 2 days ago
CA $213
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Thu., Jan. 16 from Boston to Chicago, returning Wed., Jan. 22, priced at CA $213 found 2 days ago
Delta
Mon., Jan. 13 - Wed., Jan. 15
BOS
Boston
ORD
Chicago
CA $220 Roundtrip, found 5 days ago
CA $220
Roundtrip
found 5 days ago
Select Delta flight, departing Mon., Jan. 13 from Boston to Chicago, returning Wed., Jan. 15, priced at CA $220 found 5 days ago
JetBlue Airways
Mon., Jan. 13 - Wed., Jan. 15
BOS
Boston
ORD
Chicago
CA $221 Roundtrip, found 5 days ago
CA $221
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Mon., Jan. 13 from Boston to Chicago, returning Wed., Jan. 15, priced at CA $221 found 5 days ago
JetBlue Airways
Tue., Feb. 11 - Wed., Feb. 12
BOS
Boston
ORD
Chicago
CA $223 Roundtrip, found 2 days ago
CA $223
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue., Feb. 11 from Boston to Chicago, returning Wed., Feb. 12, priced at CA $223 found 2 days ago
Delta
Tue., Feb. 11 - Tue., Feb. 11
BOS
Boston
ORD
Chicago
CA $224 Roundtrip, found 2 days ago
CA $224
Roundtrip
found 2 days ago
Select Delta flight, departing Tue., Feb. 11 from Boston to Chicago, returning Tue., Feb. 11, priced at CA $224 found 2 days ago
American Airlines
Wed., Feb. 5 - Wed., Feb. 5
BOS
Boston
ORD
Chicago
CA $224 Roundtrip, found 2 days ago
CA $224
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed., Feb. 5 from Boston to Chicago, returning Wed., Feb. 5, priced at CA $224 found 2 days ago
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
Roundtrip price
CA $172
Distance
1381 km

Boston to Chicago Flights

Ready for an adventure? Thought so! Prepare to see the sights when you book your trip from Boston to Chicago 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 BOS to ORD 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 Boston to Chicago 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 BOS to ORD. 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 Chicago 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 Logan Intl. Airport to ORD?
If you’re planning on traveling from BOS to O’Hare Airport, round-trip flights start from CA $172. 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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