Flights from Boston to Winnetka

Cheapest flights from Boston

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, May 28 - Thu, Jun 5

BOS

Logan Intl.

ORD

O'Hare Intl.

$99 Roundtrip, found 1 day ago

$99

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Wed, May 28 from Logan Intl. to O'Hare Intl., returning Thu, Jun 5, priced at $99 found 1 day ago

Sun, May 25 - Thu, Jun 5

BOS

Logan Intl.

ORD

O'Hare Intl.

$108 Roundtrip, found 1 day ago

$108

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Sun, May 25 from Logan Intl. to O'Hare Intl., returning Thu, Jun 5, priced at $108 found 1 day ago

Wed, May 28 - Sat, May 31

BOS

Logan Intl.

ORD

O'Hare Intl.

$117 Roundtrip, found 1 day ago

$117

Roundtrip

found 1 day ago

Select Delta flight, departing Wed, May 28 from Logan Intl. to O'Hare Intl., returning Sat, May 31, priced at $117 found 1 day ago

Thu, May 29 - Thu, Jun 5

BOS

Logan Intl.

ORD

O'Hare Intl.

$137 Roundtrip, found 1 day ago

$137

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Thu, May 29 from Logan Intl. to O'Hare Intl., returning Thu, Jun 5, priced at $137 found 1 day ago

Mon, May 26 - Thu, Jun 5

BOS

Logan Intl.

ORD

O'Hare Intl.

$139 Roundtrip, found 1 day ago

$139

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Mon, May 26 from Logan Intl. to O'Hare Intl., returning Thu, Jun 5, priced at $139 found 1 day ago

Wed, May 28 - Tue, Jun 3

BOS

Logan Intl.

ORD

O'Hare Intl.

$140 Roundtrip, found 1 day ago

$140

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, May 28 from Logan Intl. to O'Hare Intl., returning Tue, Jun 3, priced at $140 found 1 day ago

Sun, May 25 - Wed, May 28

BOS

Logan Intl.

ORD

O'Hare Intl.

$146 Roundtrip, found 1 day ago

$146

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Sun, May 25 from Logan Intl. to O'Hare Intl., returning Wed, May 28, priced at $146 found 1 day ago

Thu, May 29 - Tue, Jun 3

BOS

Logan Intl.

ORD

O'Hare Intl.

$151 Roundtrip, found 1 day ago

$151

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Thu, May 29 from Logan Intl. to O'Hare Intl., returning Tue, Jun 3, priced at $151 found 1 day ago

Sun, May 25 - Tue, Jun 3

BOS

Logan Intl.

ORD

O'Hare Intl.

$160 Roundtrip, found 1 day ago

$160

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Sun, May 25 from Logan Intl. to O'Hare Intl., returning Tue, Jun 3, priced at $160 found 1 day ago

Wed, May 28 - Mon, Jun 2

BOS

Logan Intl.

ORD

O'Hare Intl.

$163 Roundtrip, found 1 day ago

$163

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, May 28 from Logan Intl. to O'Hare Intl., returning Mon, Jun 2, priced at $163 found 1 day ago

Fri, May 23 - Thu, Jun 5

BOS

Logan Intl.

ORD

O'Hare Intl.

$163 Roundtrip, found 1 day ago

$163

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Fri, May 23 from Logan Intl. to O'Hare Intl., returning Thu, Jun 5, priced at $163 found 1 day ago

Sat, May 24 - Tue, Jun 3

BOS

Logan Intl.

ORD

O'Hare Intl.

$167 Roundtrip, found 1 day ago

$167

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, May 24 from Logan Intl. to O'Hare Intl., returning Tue, Jun 3, priced at $167 found 1 day ago

Thu, May 29 - Sat, May 31

BOS

Logan Intl.

ORD

O'Hare Intl.

$169 Roundtrip, found 1 day ago

$169

Roundtrip

found 1 day ago

Select United flight, departing Thu, May 29 from Logan Intl. to O'Hare Intl., returning Sat, May 31, priced at $169 found 1 day ago

Thu, May 29 - Sun, Jun 1

BOS

Logan Intl.

ORD

O'Hare Intl.

$171 Roundtrip, found 1 day ago

$171

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Thu, May 29 from Logan Intl. to O'Hare Intl., returning Sun, Jun 1, priced at $171 found 1 day ago

Thu, May 29 - Mon, Jun 2

BOS

Logan Intl.

ORD

O'Hare Intl.

$173 Roundtrip, found 1 day ago

$173

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Thu, May 29 from Logan Intl. to O'Hare Intl., returning Mon, Jun 2, priced at $173 found 1 day ago

Sat, May 24 - Sat, May 24

BOS

Logan Intl.

ORD

O'Hare Intl.

$187 Roundtrip, found 1 day ago

$187

Roundtrip

found 1 day ago

Select United flight, departing Sat, May 24 from Logan Intl. to O'Hare Intl., returning Sat, May 24, priced at $187 found 1 day ago

Mon, May 26 - Tue, May 27

BOS

Logan Intl.

ORD

O'Hare Intl.

$188 Roundtrip, found 1 day ago

$188

Roundtrip

found 1 day ago

Select American Airlines flight, departing Mon, May 26 from Logan Intl. to O'Hare Intl., returning Tue, May 27, priced at $188 found 1 day ago

Sat, May 24 - Mon, Jun 2

BOS

Logan Intl.

ORD

O'Hare Intl.

$190 Roundtrip, found 1 day ago

$190

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, May 24 from Logan Intl. to O'Hare Intl., returning Mon, Jun 2, priced at $190 found 1 day ago

Fri, Jun 6 - Sat, Jun 7

BOS

Logan Intl.

ORD

O'Hare Intl.

$210 Roundtrip, found 6 days ago

$210

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Fri, Jun 6 from Logan Intl. to O'Hare Intl., returning Sat, Jun 7, priced at $210 found 6 days ago

Sat, May 24 - Sun, May 25

MHT

Manchester-Boston Regional

ORD

O'Hare Intl.

$367 Roundtrip, found 4 days ago

$367

Roundtrip

found 4 days ago

Select American Airlines flight, departing Sat, May 24 from Manchester-Boston Regional to O'Hare Intl., returning Sun, May 25, priced at $367 found 4 days ago