Flights from Boston to West Chicago

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.

Thu, Aug 21 - Mon, Aug 25

BOS

Logan Intl.

ORD

O'Hare Intl.

$121 Roundtrip, found 6 days ago

$121

Roundtrip

found 6 days ago

Select United flight, departing Thu, Aug 21 from Logan Intl. to O'Hare Intl., returning Mon, Aug 25, priced at $121 found 6 days ago

Thu, Aug 21 - Mon, Aug 25

BOS

Logan Intl.

ORD

O'Hare Intl.

$129 Roundtrip, found 6 days ago

$129

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Thu, Aug 21 from Logan Intl. to O'Hare Intl., returning Mon, Aug 25, priced at $129 found 6 days ago

Mon, Aug 18 - Wed, Aug 20

BOS

Logan Intl.

ORD

O'Hare Intl.

$136 Roundtrip, found 6 days ago

$136

Roundtrip

found 6 days ago

Select Delta flight, departing Mon, Aug 18 from Logan Intl. to O'Hare Intl., returning Wed, Aug 20, priced at $136 found 6 days ago

Tue, Aug 19 - Tue, Aug 26

BOS

Logan Intl.

ORD

O'Hare Intl.

$137 Roundtrip, found 6 days ago

$137

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Tue, Aug 19 from Logan Intl. to O'Hare Intl., returning Tue, Aug 26, priced at $137 found 6 days ago

Tue, Nov 4 - Thu, Nov 6

BOS

Logan Intl.

ORD

O'Hare Intl.

$137 Roundtrip, found 2 hours ago

$137

Roundtrip

found 2 hours ago

Select Delta flight, departing Tue, Nov 4 from Logan Intl. to O'Hare Intl., returning Thu, Nov 6, priced at $137 found 2 hours ago

Tue, Nov 4 - Thu, Nov 6

BOS

Logan Intl.

ORD

O'Hare Intl.

$137 Roundtrip, found 2 hours ago

$137

Roundtrip

found 2 hours ago

Select American Airlines flight, departing Tue, Nov 4 from Logan Intl. to O'Hare Intl., returning Thu, Nov 6, priced at $137 found 2 hours ago

Tue, Nov 4 - Thu, Nov 6

BOS

Logan Intl.

ORD

O'Hare Intl.

$139 Roundtrip, found 2 hours ago

$139

Roundtrip

found 2 hours ago

Select Spirit Airlines flight, departing Tue, Nov 4 from Logan Intl. to O'Hare Intl., returning Thu, Nov 6, priced at $139 found 2 hours ago

Thu, Aug 21 - Mon, Aug 25

BOS

Logan Intl.

ORD

O'Hare Intl.

$139 Roundtrip, found 6 days ago

$139

Roundtrip

found 6 days ago

Select Delta flight, departing Thu, Aug 21 from Logan Intl. to O'Hare Intl., returning Mon, Aug 25, priced at $139 found 6 days ago

Mon, Aug 18 - Tue, Aug 26

BOS

Logan Intl.

ORD

O'Hare Intl.

$147 Roundtrip, found 6 days ago

$147

Roundtrip

found 6 days ago

Select Delta flight, departing Mon, Aug 18 from Logan Intl. to O'Hare Intl., returning Tue, Aug 26, priced at $147 found 6 days ago

Tue, Nov 4 - Thu, Nov 6

BOS

Logan Intl.

ORD

O'Hare Intl.

$149 Roundtrip, found 2 hours ago

$149

Roundtrip

found 2 hours ago

Select Spirit Airlines flight, departing Tue, Nov 4 from Logan Intl. to O'Hare Intl., returning Thu, Nov 6, priced at $149 found 2 hours ago

Tue, Nov 4 - Thu, Nov 6

BOS

Logan Intl.

ORD

O'Hare Intl.

$153 Roundtrip, found 2 hours ago

$153

Roundtrip

found 2 hours ago

Select United flight, departing Tue, Nov 4 from Logan Intl. to O'Hare Intl., returning Thu, Nov 6, priced at $153 found 2 hours ago

Tue, Nov 4 - Thu, Nov 6

BOS

Logan Intl.

ORD

O'Hare Intl.

$154 Roundtrip, found 2 hours ago

$154

Roundtrip

found 2 hours ago

Select Spirit Airlines flight, departing Tue, Nov 4 from Logan Intl. to O'Hare Intl., returning Thu, Nov 6, priced at $154 found 2 hours ago

Tue, Nov 4 - Thu, Nov 6

BOS

Logan Intl.

ORD

O'Hare Intl.

$155 Roundtrip, found 2 hours ago

$155

Roundtrip

found 2 hours ago

Select United flight, departing Tue, Nov 4 from Logan Intl. to O'Hare Intl., returning Thu, Nov 6, priced at $155 found 2 hours ago

Thu, Aug 21 - Mon, Aug 25

BOS

Logan Intl.

ORD

O'Hare Intl.

$156 Roundtrip, found 6 days ago

$156

Roundtrip

found 6 days ago

Select American Airlines flight, departing Thu, Aug 21 from Logan Intl. to O'Hare Intl., returning Mon, Aug 25, priced at $156 found 6 days ago

Mon, Aug 18 - Wed, Aug 20

BOS

Logan Intl.

ORD

O'Hare Intl.

$157 Roundtrip, found 6 days ago

$157

Roundtrip

found 6 days ago

Select Delta flight, departing Mon, Aug 18 from Logan Intl. to O'Hare Intl., returning Wed, Aug 20, priced at $157 found 6 days ago

Thu, Aug 21 - Mon, Aug 25

BOS

Logan Intl.

ORD

O'Hare Intl.

$159 Roundtrip, found 6 days ago

$159

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Thu, Aug 21 from Logan Intl. to O'Hare Intl., returning Mon, Aug 25, priced at $159 found 6 days ago

Tue, Nov 4 - Thu, Nov 6

BOS

Logan Intl.

ORD

O'Hare Intl.

$167 Roundtrip, found 2 hours ago

$167

Roundtrip

found 2 hours ago

Select Spirit Airlines flight, departing Tue, Nov 4 from Logan Intl. to O'Hare Intl., returning Thu, Nov 6, priced at $167 found 2 hours ago

Wed, Aug 13 - Wed, Aug 13

MHT

Manchester-Boston Regional

ORD

O'Hare Intl.

$206 Roundtrip, found 6 days ago

$206

Roundtrip

found 6 days ago

Select American Airlines flight, departing Wed, Aug 13 from Manchester-Boston Regional to O'Hare Intl., returning Wed, Aug 13, priced at $206 found 6 days ago

Sat, Aug 16 - Sat, Aug 23

BOS

Logan Intl.

ORD

O'Hare Intl.

$208 Roundtrip, found 6 days ago

$208

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Sat, Aug 16 from Logan Intl. to O'Hare Intl., returning Sat, Aug 23, priced at $208 found 6 days ago

Tue, Nov 4 - Thu, Nov 6

PVD

T.F. Green

ORD

O'Hare Intl.

$234 Roundtrip, found 2 hours ago

$234

Roundtrip

found 2 hours ago

Select American Airlines flight, departing Tue, Nov 4 from T.F. Green to O'Hare Intl., returning Thu, Nov 6, priced at $234 found 2 hours ago