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

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Find The Best Dates To Fly

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

The cheapest flights to Logan Intl. found within the past 7 days were CA $202 round trip and CA $94 one way. Prices and availability subject to change. Additional terms may apply.

Fri, Apr 10 - Tue, Apr 14
ORD
Chicago
BOS
Boston
CA $202 Roundtrip, found 1 hour ago
CA $202
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Fri, Apr 10 from Chicago to Boston, returning Tue, Apr 14, priced at CA $202 found 1 hour ago
Tue, May 12 - Sat, May 16
ORD
Chicago
BOS
Boston
CA $209 Roundtrip, found 23 hours ago
CA $209
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Tue, May 12 from Chicago to Boston, returning Sat, May 16, priced at CA $209 found 23 hours ago
Mon, Apr 20 - Thu, Apr 23
ORD
Chicago
BOS
Boston
CA $221 Roundtrip, found 1 day ago
CA $221
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Apr 20 from Chicago to Boston, returning Thu, Apr 23, priced at CA $221 found 1 day ago
Thu, Apr 16 - Wed, Apr 22
ORD
Chicago
BOS
Boston
CA $230 Roundtrip, found 1 day ago
CA $230
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Apr 16 from Chicago to Boston, returning Wed, Apr 22, priced at CA $230 found 1 day ago
Tue, Apr 7 - Sat, Apr 11
ORD
Chicago
BOS
Boston
CA $235 Roundtrip, found 3 days ago
CA $235
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, Apr 7 from Chicago to Boston, returning Sat, Apr 11, priced at CA $235 found 3 days ago
Fri, Apr 10 - Tue, Apr 14
ORD
Chicago
BOS
Boston
CA $242 Roundtrip, found 1 hour ago
CA $242
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Fri, Apr 10 from Chicago to Boston, returning Tue, Apr 14, priced at CA $242 found 1 hour ago
Mon, Apr 20 - Thu, Apr 23
ORD
Chicago
BOS
Boston
CA $242 Roundtrip, found 1 day ago
CA $242
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Apr 20 from Chicago to Boston, returning Thu, Apr 23, priced at CA $242 found 1 day ago
Tue, Apr 7 - Sat, Apr 11
ORD
Chicago
BOS
Boston
CA $249 Roundtrip, found 3 days ago
CA $249
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Apr 7 from Chicago to Boston, returning Sat, Apr 11, priced at CA $249 found 3 days ago
Mon, Apr 20 - Thu, Apr 23
ORD
Chicago
BOS
Boston
CA $261 Roundtrip, found 1 day ago
CA $261
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Mon, Apr 20 from Chicago to Boston, returning Thu, Apr 23, priced at CA $261 found 1 day ago
Thu, Apr 16 - Wed, Apr 22
ORD
Chicago
BOS
Boston
CA $281 Roundtrip, found 1 day ago
CA $281
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Apr 16 from Chicago to Boston, returning Wed, Apr 22, priced at CA $281 found 1 day 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.

Explore More Ways to Travel with 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.