Flights to Western Suburbs from Boston - $57

Cheap Flights from Boston to Western Suburbs (BOS-CHI)

Prices were available within the past 7 days and start at $57 for one-way flights and $97 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Aug 28 - Wed, Sep 3

BOS

Boston

MDW

Chicago

$97 Roundtrip, found 16 hours ago

$97

Roundtrip

found 16 hours ago

Select Southwest Airlines flight, departing Thu, Aug 28 from Boston to Chicago, returning Wed, Sep 3, priced at $97 found 16 hours ago

Tue, Nov 11 - Wed, Nov 12

BOS

Boston

MDW

Chicago

$102 Roundtrip, found 1 day ago

$102

Roundtrip

found 1 day ago

Select Southwest Airlines flight, departing Tue, Nov 11 from Boston to Chicago, returning Wed, Nov 12, priced at $102 found 1 day ago

Wed, Sep 3 - Sat, Sep 13

BOS

Boston

ORD

Chicago

$107 Roundtrip, found 17 hours ago

$107

Roundtrip

found 17 hours ago

Select JetBlue Airways flight, departing Wed, Sep 3 from Boston to Chicago, returning Sat, Sep 13, priced at $107 found 17 hours ago

Tue, Aug 19 - Wed, Aug 20

BOS

Boston

ORD

Chicago

$114 Roundtrip, found 11 hours ago

$114

Roundtrip

found 11 hours ago

Select Spirit Airlines flight, departing Tue, Aug 19 from Boston to Chicago, returning Wed, Aug 20, priced at $114 found 11 hours ago

Mon, Sep 8 - Thu, Sep 18

BOS

Boston

ORD

Chicago

$116 Roundtrip, found 17 hours ago

$116

Roundtrip

found 17 hours ago

Select United flight, departing Mon, Sep 8 from Boston to Chicago, returning Thu, Sep 18, priced at $116 found 17 hours ago

Sat, Aug 30 - Tue, Sep 2

BOS

Boston

ORD

Chicago

$117 Roundtrip, just found

$117

Roundtrip

just found

Select American Airlines flight, departing Sat, Aug 30 from Boston to Chicago, returning Tue, Sep 2, priced at $117 just found