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

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 Boston (BOS) to Chicago (ORD)

The cheapest flights to O'Hare Intl. found within the past 7 days were CA $161 round trip and CA $79 one way. Prices and availability subject to change. Additional terms may apply.

Mon, Sep. 1 - Tue, Sep. 2
BOS
Boston
ORD
Chicago
CA $161 Roundtrip, found 3 days ago
CA $161
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Mon, Sep. 1 from Boston to Chicago, returning Tue, Sep. 2, priced at CA $161 found 3 days ago
Thu, Sep. 4 - Mon, Sep. 8
BOS
Boston
ORD
Chicago
CA $180 Roundtrip, found 1 hour ago
CA $180
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Thu, Sep. 4 from Boston to Chicago, returning Mon, Sep. 8, priced at CA $180 found 1 hour ago
Fri, Aug. 22 - Mon, Aug. 25
BOS
Boston
ORD
Chicago
CA $191 Roundtrip, found 4 days ago
CA $191
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Aug. 22 from Boston to Chicago, returning Mon, Aug. 25, priced at CA $191 found 4 days ago
Thu, Aug. 28 - Wed, Sep. 3
BOS
Boston
ORD
Chicago
CA $214 Roundtrip, found 3 days ago
CA $214
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Thu, Aug. 28 from Boston to Chicago, returning Wed, Sep. 3, priced at CA $214 found 3 days ago
Thu, Sep. 4 - Mon, Sep. 8
BOS
Boston
ORD
Chicago
CA $216 Roundtrip, found 1 hour ago
CA $216
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Thu, Sep. 4 from Boston to Chicago, returning Mon, Sep. 8, priced at CA $216 found 1 hour ago
Thu, Aug. 28 - Wed, Sep. 3
BOS
Boston
ORD
Chicago
CA $217 Roundtrip, found 3 days ago
CA $217
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Thu, Aug. 28 from Boston to Chicago, returning Wed, Sep. 3, priced at CA $217 found 3 days ago
Thu, Sep. 4 - Mon, Sep. 8
BOS
Boston
ORD
Chicago
CA $221 Roundtrip, found 1 hour ago
CA $221
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Thu, Sep. 4 from Boston to Chicago, returning Mon, Sep. 8, priced at CA $221 found 1 hour ago
Fri, Aug. 22 - Mon, Aug. 25
BOS
Boston
ORD
Chicago
CA $223 Roundtrip, found 4 days ago
CA $223
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Aug. 22 from Boston to Chicago, returning Mon, Aug. 25, priced at CA $223 found 4 days ago
Thu, Sep. 4 - Mon, Sep. 8
BOS
Boston
ORD
Chicago
CA $230 Roundtrip, found 1 hour ago
CA $230
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Thu, Sep. 4 from Boston to Chicago, returning Mon, Sep. 8, priced at CA $230 found 1 hour ago
Thu, Sep. 4 - Mon, Sep. 8
BOS
Boston
ORD
Chicago
CA $236 Roundtrip, found 1 hour ago
CA $236
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Thu, Sep. 4 from Boston to Chicago, returning Mon, Sep. 8, priced at CA $236 found 1 hour ago

Frequently asked questions

Are there direct flights from Logan Intl. Airport to ORD?
Your next unforgettable adventure is on the other side of just one flight. You can jet direct from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD) with multiple airlines, including United Airlines and American Airlines.
What airlines fly from BOS to ORD?
With a range of airlines operating direct flights from BOS to O'Hare Intl. Airport (ORD), you're spoiled for choice. Here are some of the most well-known air carriers:

  • United Airlines - (UA) with 208 flights every month
  • American Airlines - (AA) with 195 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 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!

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!

*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.