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Selected fares from Chicago to The Berkshires
The cheapest prices found with in the last 7 days for return flights were $97 and $49 for one-way flights to The Berkshires for the period specified. Prices and availability are subject to change. Additional terms apply.
Wed, Sep 11 - Sat, Sep 14
ORD
O'Hare Intl.
BDL
Bradley Intl.
$97 Roundtrip, found 4 days ago
$97
Roundtrip
found 4 days ago
Tue, Sep 17 - Fri, Sep 20
ORD
O'Hare Intl.
ALB
Albany Intl.
$125 Roundtrip, found 5 days ago
$125
Roundtrip
found 5 days ago
Sat, Sep 14 - Tue, Sep 17
ORD
O'Hare Intl.
ALB
Albany Intl.
$125 Roundtrip, found 5 days ago
$125
Roundtrip
found 5 days ago
More to explore for Chicago to The Berkshires
Other Flights to The Berkshires
- Chicago to The Berkshires
- Newark to The Berkshires
- Los Angeles to The Berkshires
- Washington to The Berkshires
- Tampa to The Berkshires
- Miami to The Berkshires
- Portland to The Berkshires
- Fort Lauderdale to The Berkshires
- New York to The Berkshires
- Charlotte to The Berkshires
- Denver to The Berkshires
- Seattle to The Berkshires
- Dallas to The Berkshires
- Orlando to The Berkshires
- Atlanta to The Berkshires
- San Francisco to The Berkshires
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