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 22 hours ago

$99

Roundtrip

found 22 hours ago

Select JetBlue Airways flight, departing Wed, May 28 from Logan Intl. to O'Hare Intl., returning Thu, Jun 5, priced at $99 found 22 hours ago

Sun, May 25 - Thu, Jun 5

BOS

Logan Intl.

ORD

O'Hare Intl.

$108 Roundtrip, found 22 hours ago

$108

Roundtrip

found 22 hours ago

Select JetBlue Airways flight, departing Sun, May 25 from Logan Intl. to O'Hare Intl., returning Thu, Jun 5, priced at $108 found 22 hours ago

Fri, Aug 15 - Sun, Aug 17

BOS

Logan Intl.

ORD

O'Hare Intl.

$117 Roundtrip, found 6 days ago

$117

Roundtrip

found 6 days ago

Select United flight, departing Fri, Aug 15 from Logan Intl. to O'Hare Intl., returning Sun, Aug 17, priced at $117 found 6 days ago

Wed, May 28 - Sat, May 31

BOS

Logan Intl.

ORD

O'Hare Intl.

$117 Roundtrip, found 22 hours ago

$117

Roundtrip

found 22 hours ago

Select Delta flight, departing Wed, May 28 from Logan Intl. to O'Hare Intl., returning Sat, May 31, priced at $117 found 22 hours ago

Fri, Aug 15 - Sun, Aug 17

BOS

Logan Intl.

ORD

O'Hare Intl.

$117 Roundtrip, found 6 days ago

$117

Roundtrip

found 6 days ago

Select United flight, departing Fri, Aug 15 from Logan Intl. to O'Hare Intl., returning Sun, Aug 17, priced at $117 found 6 days ago

Fri, Aug 15 - Sun, Aug 17

BOS

Logan Intl.

ORD

O'Hare Intl.

$117 Roundtrip, found 6 days ago

$117

Roundtrip

found 6 days ago

Select American Airlines flight, departing Fri, Aug 15 from Logan Intl. to O'Hare Intl., returning Sun, Aug 17, priced at $117 found 6 days ago

Fri, Aug 15 - Sun, Aug 17

BOS

Logan Intl.

ORD

O'Hare Intl.

$123 Roundtrip, found 6 days ago

$123

Roundtrip

found 6 days ago

Select United flight, departing Fri, Aug 15 from Logan Intl. to O'Hare Intl., returning Sun, Aug 17, priced at $123 found 6 days ago

Thu, May 29 - Thu, Jun 5

BOS

Logan Intl.

ORD

O'Hare Intl.

$137 Roundtrip, found 22 hours ago

$137

Roundtrip

found 22 hours ago

Select JetBlue Airways flight, departing Thu, May 29 from Logan Intl. to O'Hare Intl., returning Thu, Jun 5, priced at $137 found 22 hours ago

Mon, May 26 - Thu, Jun 5

BOS

Logan Intl.

ORD

O'Hare Intl.

$139 Roundtrip, found 22 hours ago

$139

Roundtrip

found 22 hours ago

Select JetBlue Airways flight, departing Mon, May 26 from Logan Intl. to O'Hare Intl., returning Thu, Jun 5, priced at $139 found 22 hours ago

Wed, May 28 - Tue, Jun 3

BOS

Logan Intl.

ORD

O'Hare Intl.

$140 Roundtrip, found 22 hours ago

$140

Roundtrip

found 22 hours ago

Select Spirit Airlines flight, departing Wed, May 28 from Logan Intl. to O'Hare Intl., returning Tue, Jun 3, priced at $140 found 22 hours ago

Fri, Aug 15 - Sun, Aug 17

BOS

Logan Intl.

ORD

O'Hare Intl.

$145 Roundtrip, found 6 days ago

$145

Roundtrip

found 6 days ago

Select United flight, departing Fri, Aug 15 from Logan Intl. to O'Hare Intl., returning Sun, Aug 17, priced at $145 found 6 days ago

Sun, May 25 - Wed, May 28

BOS

Logan Intl.

ORD

O'Hare Intl.

$146 Roundtrip, found 22 hours ago

$146

Roundtrip

found 22 hours ago

Select JetBlue Airways flight, departing Sun, May 25 from Logan Intl. to O'Hare Intl., returning Wed, May 28, priced at $146 found 22 hours ago

Thu, May 29 - Tue, Jun 3

BOS

Logan Intl.

ORD

O'Hare Intl.

$151 Roundtrip, found 22 hours ago

$151

Roundtrip

found 22 hours ago

Select Spirit Airlines flight, departing Thu, May 29 from Logan Intl. to O'Hare Intl., returning Tue, Jun 3, priced at $151 found 22 hours ago

Fri, Aug 15 - Sun, Aug 17

BOS

Logan Intl.

ORD

O'Hare Intl.

$152 Roundtrip, found 6 days ago

$152

Roundtrip

found 6 days ago

Select United flight, departing Fri, Aug 15 from Logan Intl. to O'Hare Intl., returning Sun, Aug 17, priced at $152 found 6 days ago

Fri, Aug 15 - Sun, Aug 17

BOS

Logan Intl.

ORD

O'Hare Intl.

$155 Roundtrip, found 6 days ago

$155

Roundtrip

found 6 days ago

Select United flight, departing Fri, Aug 15 from Logan Intl. to O'Hare Intl., returning Sun, Aug 17, priced at $155 found 6 days ago

Sun, May 25 - Tue, Jun 3

BOS

Logan Intl.

ORD

O'Hare Intl.

$160 Roundtrip, found 22 hours ago

$160

Roundtrip

found 22 hours ago

Select JetBlue Airways flight, departing Sun, May 25 from Logan Intl. to O'Hare Intl., returning Tue, Jun 3, priced at $160 found 22 hours ago

Wed, May 28 - Mon, Jun 2

BOS

Logan Intl.

ORD

O'Hare Intl.

$163 Roundtrip, found 22 hours ago

$163

Roundtrip

found 22 hours ago

Select Spirit Airlines flight, departing Wed, May 28 from Logan Intl. to O'Hare Intl., returning Mon, Jun 2, priced at $163 found 22 hours ago

Fri, May 23 - Thu, Jun 5

BOS

Logan Intl.

ORD

O'Hare Intl.

$163 Roundtrip, found 22 hours ago

$163

Roundtrip

found 22 hours ago

Select JetBlue Airways flight, departing Fri, May 23 from Logan Intl. to O'Hare Intl., returning Thu, Jun 5, priced at $163 found 22 hours 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