Flights from Boston to Winfield

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.

Tue, Jan 27 - Tue, Feb 10

BOS

Logan Intl.

ORD

O'Hare Intl.

$132 Roundtrip, found 3 days ago

$132

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Tue, Jan 27 from Logan Intl. to O'Hare Intl., returning Tue, Feb 10, priced at $132 found 3 days ago

Thu, Jan 1 - Sat, Jan 17

BOS

Logan Intl.

ORD

O'Hare Intl.

$132 Roundtrip, found 3 days ago

$132

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Thu, Jan 1 from Logan Intl. to O'Hare Intl., returning Sat, Jan 17, priced at $132 found 3 days ago

Thu, Jan 1 - Mon, Jan 12

BOS

Logan Intl.

ORD

O'Hare Intl.

$137 Roundtrip, found 3 days ago

$137

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Thu, Jan 1 from Logan Intl. to O'Hare Intl., returning Mon, Jan 12, priced at $137 found 3 days ago

Wed, Feb 18 - Fri, Feb 27

BOS

Logan Intl.

ORD

O'Hare Intl.

$147 Roundtrip, found 3 days ago

$147

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Wed, Feb 18 from Logan Intl. to O'Hare Intl., returning Fri, Feb 27, priced at $147 found 3 days ago

Thu, Feb 19 - Mon, Mar 9

BOS

Logan Intl.

ORD

O'Hare Intl.

$152 Roundtrip, found 3 days ago

$152

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Thu, Feb 19 from Logan Intl. to O'Hare Intl., returning Mon, Mar 9, priced at $152 found 3 days ago

Thu, Jan 1 - Mon, Jan 12

BOS

Logan Intl.

MDW

Midway Intl.

$152 Roundtrip, found 3 days ago

$152

Roundtrip

found 3 days ago

Select Southwest Airlines flight, departing Thu, Jan 1 from Logan Intl. to Midway Intl., returning Mon, Jan 12, priced at $152 found 3 days ago

Fri, Jan 2 - Tue, Jan 13

BOS

Logan Intl.

MDW

Midway Intl.

$157 Roundtrip, found 3 days ago

$157

Roundtrip

found 3 days ago

Select Southwest Airlines flight, departing Fri, Jan 2 from Logan Intl. to Midway Intl., returning Tue, Jan 13, priced at $157 found 3 days ago

Thu, Feb 19 - Sat, Mar 7

BOS

Logan Intl.

ORD

O'Hare Intl.

$160 Roundtrip, found 3 days ago

$160

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Thu, Feb 19 from Logan Intl. to O'Hare Intl., returning Sat, Mar 7, priced at $160 found 3 days ago

Thu, Jan 1 - Mon, Jan 12

BOS

Logan Intl.

MDW

Midway Intl.

$162 Roundtrip, found 3 days ago

$162

Roundtrip

found 3 days ago

Select Southwest Airlines flight, departing Thu, Jan 1 from Logan Intl. to Midway Intl., returning Mon, Jan 12, priced at $162 found 3 days ago

Thu, Jan 1 - Fri, Jan 16

BOS

Logan Intl.

ORD

O'Hare Intl.

$170 Roundtrip, found 3 days ago

$170

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Thu, Jan 1 from Logan Intl. to O'Hare Intl., returning Fri, Jan 16, priced at $170 found 3 days ago

Thu, Jan 1 - Mon, Jan 12

BOS

Logan Intl.

MDW

Midway Intl.

$172 Roundtrip, found 3 days ago

$172

Roundtrip

found 3 days ago

Select Southwest Airlines flight, departing Thu, Jan 1 from Logan Intl. to Midway Intl., returning Mon, Jan 12, priced at $172 found 3 days ago

Fri, Jan 2 - Tue, Jan 13

BOS

Logan Intl.

MDW

Midway Intl.

$172 Roundtrip, found 3 days ago

$172

Roundtrip

found 3 days ago

Select Southwest Airlines flight, departing Fri, Jan 2 from Logan Intl. to Midway Intl., returning Tue, Jan 13, priced at $172 found 3 days ago

Sun, Jan 11 - Sun, Jan 25

BOS

Logan Intl.

ORD

O'Hare Intl.

$176 Roundtrip, found 3 days ago

$176

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Sun, Jan 11 from Logan Intl. to O'Hare Intl., returning Sun, Jan 25, priced at $176 found 3 days ago

Sun, Jan 4 - Thu, Jan 15

BOS

Logan Intl.

MDW

Midway Intl.

$177 Roundtrip, found 3 days ago

$177

Roundtrip

found 3 days ago

Select Southwest Airlines flight, departing Sun, Jan 4 from Logan Intl. to Midway Intl., returning Thu, Jan 15, priced at $177 found 3 days ago

Fri, Jan 2 - Tue, Jan 20

BOS

Logan Intl.

ORD

O'Hare Intl.

$177 Roundtrip, found 3 days ago

$177

Roundtrip

found 3 days ago

Select Delta flight, departing Fri, Jan 2 from Logan Intl. to O'Hare Intl., returning Tue, Jan 20, priced at $177 found 3 days ago

Thu, Jan 1 - Mon, Jan 12

BOS

Logan Intl.

MDW

Midway Intl.

$182 Roundtrip, found 3 days ago

$182

Roundtrip

found 3 days ago

Select Southwest Airlines flight, departing Thu, Jan 1 from Logan Intl. to Midway Intl., returning Mon, Jan 12, priced at $182 found 3 days ago

Wed, Dec 31 - Sun, Jan 11

BOS

Logan Intl.

ORD

O'Hare Intl.

$182 Roundtrip, found 3 days ago

$182

Roundtrip

found 3 days ago

Select United flight, departing Wed, Dec 31 from Logan Intl. to O'Hare Intl., returning Sun, Jan 11, priced at $182 found 3 days ago

Sat, Jan 3 - Wed, Jan 14

BOS

Logan Intl.

ORD

O'Hare Intl.

$187 Roundtrip, found 3 days ago

$187

Roundtrip

found 3 days ago

Select United flight, departing Sat, Jan 3 from Logan Intl. to O'Hare Intl., returning Wed, Jan 14, priced at $187 found 3 days ago

Tue, Feb 10 - Fri, Feb 20

BOS

Logan Intl.

ORD

O'Hare Intl.

$190 Roundtrip, found 3 days ago

$190

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Tue, Feb 10 from Logan Intl. to O'Hare Intl., returning Fri, Feb 20, priced at $190 found 3 days ago

Fri, Jan 2 - Tue, Jan 13

BOS

Logan Intl.

ORD

O'Hare Intl.

$197 Roundtrip, found 3 days ago

$197

Roundtrip

found 3 days ago

Select American Airlines flight, departing Fri, Jan 2 from Logan Intl. to O'Hare Intl., returning Tue, Jan 13, priced at $197 found 3 days ago