Flights from Boston to 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.

Tue, Jul 8 - Sun, Jul 13

BOS

Logan Intl.

ORD

O'Hare Intl.

$117 Roundtrip, found 2 days ago

$117

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Jul 8 from Logan Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $117 found 2 days ago

Tue, Jul 8 - Thu, Jul 10

BOS

Logan Intl.

ORD

O'Hare Intl.

$117 Roundtrip, found 2 days ago

$117

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Jul 8 from Logan Intl. to O'Hare Intl., returning Thu, Jul 10, priced at $117 found 2 days ago

Tue, May 13 - Tue, May 13

BOS

Logan Intl.

ORD

O'Hare Intl.

$117 Roundtrip, found 10 hours ago

$117

Roundtrip

found 10 hours ago

Select JetBlue Airways flight, departing Tue, May 13 from Logan Intl. to O'Hare Intl., returning Tue, May 13, priced at $117 found 10 hours ago

Sat, Aug 16 - Fri, Aug 22

BOS

Logan Intl.

ORD

O'Hare Intl.

$117 Roundtrip, found 4 days ago

$117

Roundtrip

found 4 days ago

Select United flight, departing Sat, Aug 16 from Logan Intl. to O'Hare Intl., returning Fri, Aug 22, priced at $117 found 4 days ago

Tue, Jul 8 - Sun, Jul 13

BOS

Logan Intl.

ORD

O'Hare Intl.

$117 Roundtrip, found 2 days ago

$117

Roundtrip

found 2 days ago

Select American Airlines flight, departing Tue, Jul 8 from Logan Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $117 found 2 days ago

Tue, Jul 8 - Sun, Jul 13

BOS

Logan Intl.

ORD

O'Hare Intl.

$123 Roundtrip, found 2 days ago

$123

Roundtrip

found 2 days ago

Select United flight, departing Tue, Jul 8 from Logan Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $123 found 2 days ago

Tue, Jul 8 - Sun, Jul 13

BOS

Logan Intl.

ORD

O'Hare Intl.

$137 Roundtrip, found 2 days ago

$137

Roundtrip

found 2 days ago

Select United flight, departing Tue, Jul 8 from Logan Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $137 found 2 days ago

Tue, May 13 - Tue, May 20

BOS

Logan Intl.

ORD

O'Hare Intl.

$137 Roundtrip, found 10 hours ago

$137

Roundtrip

found 10 hours ago

Select Delta flight, departing Tue, May 13 from Logan Intl. to O'Hare Intl., returning Tue, May 20, priced at $137 found 10 hours ago

Tue, Jul 8 - Sun, Jul 13

BOS

Logan Intl.

ORD

O'Hare Intl.

$139 Roundtrip, found 2 days ago

$139

Roundtrip

found 2 days ago

Select United flight, departing Tue, Jul 8 from Logan Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $139 found 2 days ago

Tue, May 13 - Wed, May 21

BOS

Logan Intl.

ORD

O'Hare Intl.

$140 Roundtrip, found 10 hours ago

$140

Roundtrip

found 10 hours ago

Select JetBlue Airways flight, departing Tue, May 13 from Logan Intl. to O'Hare Intl., returning Wed, May 21, priced at $140 found 10 hours ago

Tue, Jul 8 - Sun, Jul 13

BOS

Logan Intl.

ORD

O'Hare Intl.

$147 Roundtrip, found 2 days ago

$147

Roundtrip

found 2 days ago

Select United flight, departing Tue, Jul 8 from Logan Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $147 found 2 days ago

Sat, Jul 5 - Thu, Jul 10

BOS

Logan Intl.

ORD

O'Hare Intl.

$148 Roundtrip, found 2 days ago

$148

Roundtrip

found 2 days ago

Select Delta flight, departing Sat, Jul 5 from Logan Intl. to O'Hare Intl., returning Thu, Jul 10, priced at $148 found 2 days ago

Tue, Jul 8 - Sun, Jul 13

BOS

Logan Intl.

ORD

O'Hare Intl.

$149 Roundtrip, found 2 days ago

$149

Roundtrip

found 2 days ago

Select United flight, departing Tue, Jul 8 from Logan Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $149 found 2 days ago

Tue, Jul 8 - Sun, Jul 13

BOS

Logan Intl.

ORD

O'Hare Intl.

$152 Roundtrip, found 2 days ago

$152

Roundtrip

found 2 days ago

Select United flight, departing Tue, Jul 8 from Logan Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $152 found 2 days ago

Sat, Aug 16 - Fri, Aug 22

BOS

Logan Intl.

ORD

O'Hare Intl.

$157 Roundtrip, found 4 days ago

$157

Roundtrip

found 4 days ago

Select United flight, departing Sat, Aug 16 from Logan Intl. to O'Hare Intl., returning Fri, Aug 22, priced at $157 found 4 days ago

Tue, Jul 8 - Sun, Jul 13

BOS

Logan Intl.

ORD

O'Hare Intl.

$159 Roundtrip, found 2 days ago

$159

Roundtrip

found 2 days ago

Select United flight, departing Tue, Jul 8 from Logan Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $159 found 2 days ago

Tue, May 13 - Thu, May 22

BOS

Logan Intl.

ORD

O'Hare Intl.

$194 Roundtrip, found 10 hours ago

$194

Roundtrip

found 10 hours ago

Select Spirit Airlines flight, departing Tue, May 13 from Logan Intl. to O'Hare Intl., returning Thu, May 22, priced at $194 found 10 hours ago

Fri, May 16 - Sat, May 24

BOS

Logan Intl.

ORD

O'Hare Intl.

$218 Roundtrip, found 10 hours ago

$218

Roundtrip

found 10 hours ago

Select Frontier Airlines flight, departing Fri, May 16 from Logan Intl. to O'Hare Intl., returning Sat, May 24, priced at $218 found 10 hours ago

Wed, Aug 13 - Thu, Aug 21

PVD

T.F. Green

ORD

O'Hare Intl.

$293 Roundtrip, found 6 days ago

$293

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Wed, Aug 13 from T.F. Green to O'Hare Intl., returning Thu, Aug 21, priced at $293 found 6 days ago

Fri, Jun 6 - Mon, Jun 9

BOS

Logan Intl.

MDW

Midway Intl.

$317 Roundtrip, found 2 days ago

$317

Roundtrip

found 2 days ago

Select Delta flight, departing Fri, Jun 6 from Logan Intl. to Midway Intl., returning Mon, Jun 9, priced at $317 found 2 days ago