Skip to main content
A spacious airport terminal with high ceilings, check-in counters, and a Starbucks coffee shop.

￥16,820 Cheap Flights from Boston (BOS) to Chicago (ORD)

Photo by by O'Hare Intl Airport
Open Photo by by O'Hare Intl Airport

Cheap Flights from Boston to Chicago (BOS-ORD)

Prices were available within the past 7 days and start at ￥16,820 for one-way flights and ￥33,640 for roundtrip, for the period specified. Prices and availability are subject to change.
American Airlines
Tue, Sep 22 - Wed, Sep 23
BOS
Boston
ORD
Chicago
￥33,640
Roundtrip
Found 5 days ago
Select American Airlines flight, departing Tue, Sep 22 from Boston to Chicago, returning Wed, Sep 23, priced at ￥33,640 Found 5 days ago
American Airlines
Sat, Sep 12 - Sun, Sep 13
BOS
Boston
ORD
Chicago
￥35,140
Roundtrip
Found 6 days ago
Select American Airlines flight, departing Sat, Sep 12 from Boston to Chicago, returning Sun, Sep 13, priced at ￥35,140 Found 6 days ago
Delta
Tue, Sep 22 - Wed, Sep 23
BOS
Boston
ORD
Chicago
￥35,360
Roundtrip
Found 5 days ago
Select Delta flight, departing Tue, Sep 22 from Boston to Chicago, returning Wed, Sep 23, priced at ￥35,360 Found 5 days ago
Delta
Tue, Oct 13 - Tue, Oct 20
BOS
Boston
ORD
Chicago
￥35,380
Roundtrip
Found 4 days ago
Select Delta flight, departing Tue, Oct 13 from Boston to Chicago, returning Tue, Oct 20, priced at ￥35,380 Found 4 days ago
American Airlines
Wed, Sep 9 - Wed, Sep 16
BOS
Boston
ORD
Chicago
￥35,490
Roundtrip
Found 22 hours ago
Select American Airlines flight, departing Wed, Sep 9 from Boston to Chicago, returning Wed, Sep 16, priced at ￥35,490 Found 22 hours ago
Delta
Sat, Sep 12 - Sun, Sep 13
BOS
Boston
ORD
Chicago
￥36,010
Roundtrip
Found 6 days ago
Select Delta flight, departing Sat, Sep 12 from Boston to Chicago, returning Sun, Sep 13, priced at ￥36,010 Found 6 days ago
American Airlines
Sun, Aug 16 - Mon, Aug 17
BOS
Boston
ORD
Chicago
￥36,650
Roundtrip
Found 5 days ago
Select American Airlines flight, departing Sun, Aug 16 from Boston to Chicago, returning Mon, Aug 17, priced at ￥36,650 Found 5 days ago
Delta
Sat, Sep 5 - Sat, Sep 19
BOS
Boston
ORD
Chicago
￥36,760
Roundtrip
Found 6 days ago
Select Delta flight, departing Sat, Sep 5 from Boston to Chicago, returning Sat, Sep 19, priced at ￥36,760 Found 6 days ago
Delta
Wed, Sep 9 - Sat, Sep 12
BOS
Boston
ORD
Chicago
￥37,210
Roundtrip
Found 2 days ago
Select Delta flight, departing Wed, Sep 9 from Boston to Chicago, returning Sat, Sep 12, priced at ￥37,210 Found 2 days ago
United
Wed, Sep 9 - Wed, Sep 16
BOS
Boston
ORD
Chicago
￥48,600
Roundtrip
Found 22 hours ago
Select United flight, departing Wed, Sep 9 from Boston to Chicago, returning Wed, Sep 16, priced at ￥48,600 Found 22 hours ago

Find the cheapest month to fly from Boston (BOS) to Chicago (ORD)

May is typically the cheapest month to fly

From ￥15,135 - ￥29,398 per traveler.

Travel information

Origin airport
Logan International Airport
Destination airport
Chicago O'Hare Intl. Airport
Distance
1,389 km away
Airlines serving
JetBlue Airways, Delta, American Airlines, United, Alaska Airlines, Frontier Airlines, Sun Country Airlines
Popular airline
JetBlue Airways
Roundtrip price
￥33,640
Average flight time
3 hours
*Available to One Key members.