Flights to Historic Route 66 from Boston - ￥6,660

View ￥6,660 flight on Thu, Aug 21, 2025Opens in a new window

Popular airlines from Boston to Historic Route 66

  • Delta

    Delta

  • American Airlines

    American Airlines

  • United

    United

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Cheap Flights from Boston to Historic Route 66 (BOS-CHI)

Prices were available within the past 7 days and start at ￥6,660 for one-way flights and ￥13,320 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Thu, Aug 21 - Mon, Aug 25
BOS
Boston
ORD
Chicago
￥13,320 Roundtrip, found 6 days ago
￥13,320
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, Aug 21 from Boston to Chicago, returning Mon, Aug 25, priced at ￥13,320 found 6 days ago
Delta
Thu, Aug 21 - Mon, Aug 25
BOS
Boston
ORD
Chicago
￥15,260 Roundtrip, found 6 days ago
￥15,260
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Aug 21 from Boston to Chicago, returning Mon, Aug 25, priced at ￥15,260 found 6 days ago
Delta
Thu, Aug 21 - Mon, Aug 25
BOS
Boston
ORD
Chicago
￥16,690 Roundtrip, found 6 days ago
￥16,690
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Aug 21 from Boston to Chicago, returning Mon, Aug 25, priced at ￥16,690 found 6 days ago
Delta
Thu, Aug 21 - Mon, Aug 25
BOS
Boston
ORD
Chicago
￥16,760 Roundtrip, found 6 days ago
￥16,760
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Aug 21 from Boston to Chicago, returning Mon, Aug 25, priced at ￥16,760 found 6 days ago
United
Thu, Aug 21 - Mon, Aug 25
BOS
Boston
ORD
Chicago
￥21,920 Roundtrip, found 6 days ago
￥21,920
Roundtrip
found 6 days ago
Select United flight, departing Thu, Aug 21 from Boston to Chicago, returning Mon, Aug 25, priced at ￥21,920 found 6 days ago
JetBlue Airways
Tue, Sep 2 - Thu, Sep 18
BOS
Boston
ORD
Chicago
￥27,420 Roundtrip, found 4 days ago
￥27,420
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Tue, Sep 2 from Boston to Chicago, returning Thu, Sep 18, priced at ￥27,420 found 4 days ago

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

September is typically the cheapest month to fly

From ￥7,033 - ￥17,144 per traveler.

Graph displaying average flight prices per month

*Available to Expedia members.