Cheap Flights From O'Hare Intl. (ORD) To Logan Intl. (BOS)

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Cheapest Flights from Chicago (ORD) to Boston (BOS)

The cheapest flights to Logan Intl. found within the past 7 days were CA $171 round trip and CA $86 one way. Prices and availability subject to change. Additional terms may apply.

Wed., Oct. 1 - Tue., Oct. 7
ORD
Chicago
BOS
Boston
CA $171 Roundtrip, found 2 days ago
CA $171
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed., Oct. 1 from Chicago to Boston, returning Tue., Oct. 7, priced at CA $171 found 2 days ago
Mon., Aug. 25 - Sat., Sep. 27
ORD
Chicago
BOS
Boston
CA $180 Roundtrip, found 6 days ago
CA $180
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Mon., Aug. 25 from Chicago to Boston, returning Sat., Sep. 27, priced at CA $180 found 6 days ago
Wed., Oct. 1 - Tue., Oct. 7
ORD
Chicago
BOS
Boston
CA $182 Roundtrip, found 2 days ago
CA $182
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed., Oct. 1 from Chicago to Boston, returning Tue., Oct. 7, priced at CA $182 found 2 days ago
Mon., Sep. 8 - Thu., Sep. 11
ORD
Chicago
BOS
Boston
CA $186 Roundtrip, found 1 day ago
CA $186
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon., Sep. 8 from Chicago to Boston, returning Thu., Sep. 11, priced at CA $186 found 1 day ago
Mon., Aug. 25 - Sat., Sep. 27
ORD
Chicago
BOS
Boston
CA $188 Roundtrip, found 6 days ago
CA $188
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Mon., Aug. 25 from Chicago to Boston, returning Sat., Sep. 27, priced at CA $188 found 6 days ago
Thu., Jul. 10 - Sun., Jul. 13
ORD
Chicago
BOS
Boston
CA $189 Roundtrip, found 23 hours ago
CA $189
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Thu., Jul. 10 from Chicago to Boston, returning Sun., Jul. 13, priced at CA $189 found 23 hours ago
Wed., Oct. 1 - Tue., Oct. 7
ORD
Chicago
BOS
Boston
CA $190 Roundtrip, found 2 days ago
CA $190
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed., Oct. 1 from Chicago to Boston, returning Tue., Oct. 7, priced at CA $190 found 2 days ago
Mon., Aug. 25 - Sat., Sep. 27
ORD
Chicago
BOS
Boston
CA $205 Roundtrip, found 6 days ago
CA $205
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon., Aug. 25 from Chicago to Boston, returning Sat., Sep. 27, priced at CA $205 found 6 days ago
Mon., Aug. 25 - Sat., Sep. 27
ORD
Chicago
BOS
Boston
CA $221 Roundtrip, found 6 days ago
CA $221
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Mon., Aug. 25 from Chicago to Boston, returning Sat., Sep. 27, priced at CA $221 found 6 days ago
Thu., Jul. 10 - Sun., Jul. 13
ORD
Chicago
BOS
Boston
CA $227 Roundtrip, found 23 hours ago
CA $227
Roundtrip
found 23 hours ago
Select Spirit Airlines flight, departing Thu., Jul. 10 from Chicago to Boston, returning Sun., Jul. 13, priced at CA $227 found 23 hours ago

Frequently asked questions

Are there direct flights from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS)?
Multiple airlines offer flights straight from O'Hare Airport to Logan Intl. Airport (BOS). Among these are United Airlines and American Airlines --- look into them if you'd prefer to touch down at Boston with no fuss.
What airlines fly from O'Hare Airport to BOS?
With good range of airlines operating direct flights from ORD to BOS, you shouldn't have a problem finding that perfect fare. Here are some of the most popular carriers:
  • United Airlines - (UA) with 208 flights every month
  • American Airlines - (AA) with 199 flights every month
  • Delta - (DL) with 147 flights every month
  • JetBlue - (B6) with 56 flights every month

What is the best day to buy a plane ticket?
Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you're looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you're browsing flight deals.
What are the cheapest days to fly?
Frequent travellers may already know this, but earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.
How far in advance can you book a flight?
Here's the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2-4 weeks prior to their travel dates.*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

Popular Flight Routes from Chicago (ORD)

Travelers at ORD love to visit these top cities. Roam to the top destinations from Chicago (ORD) today with the cheap prices from Travelocity!

Popular Flight Routes from Boston (BOS)

Travelers at BOS love to visit these top cities. Roam to the top destinations from Boston(BOS) today with the cheap prices from Travelocity!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.