Flights from Chicago to Braintree

Cheapest flights from Chicago

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.

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 1 day ago

$137

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $137 found 1 day ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 1 day ago

$137

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $137 found 1 day ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 1 day ago

$137

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $137 found 1 day ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 1 day ago

$137

Roundtrip

found 1 day ago

Select United flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $137 found 1 day ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$139 Roundtrip, found 1 day ago

$139

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $139 found 1 day ago

Sat, Oct 18 - Sat, Oct 18

ORD

O'Hare Intl.

BOS

Logan Intl.

$145 Roundtrip, found 3 days ago

$145

Roundtrip

found 3 days ago

Select Delta flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Sat, Oct 18, priced at $145 found 3 days ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$149 Roundtrip, found 1 day ago

$149

Roundtrip

found 1 day ago

Select United flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $149 found 1 day ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$153 Roundtrip, found 1 day ago

$153

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $153 found 1 day ago

Wed, Jul 30 - Tue, Aug 12

ORD

O'Hare Intl.

BOS

Logan Intl.

$155 Roundtrip, found 2 days ago

$155

Roundtrip

found 2 days ago

Select Delta flight, departing Wed, Jul 30 from O'Hare Intl. to Logan Intl., returning Tue, Aug 12, priced at $155 found 2 days ago

Sat, Aug 9 - Sat, Aug 16

ORD

O'Hare Intl.

BOS

Logan Intl.

$160 Roundtrip, found 6 days ago

$160

Roundtrip

found 6 days ago

Select United flight, departing Sat, Aug 9 from O'Hare Intl. to Logan Intl., returning Sat, Aug 16, priced at $160 found 6 days ago

Thu, Jul 3 - Mon, Jul 7

ORD

O'Hare Intl.

BOS

Logan Intl.

$163 Roundtrip, found 4 days ago

$163

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Thu, Jul 3 from O'Hare Intl. to Logan Intl., returning Mon, Jul 7, priced at $163 found 4 days ago

Tue, Jul 22 - Mon, Jul 28

ORD

O'Hare Intl.

BOS

Logan Intl.

$165 Roundtrip, found 3 days ago

$165

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Tue, Jul 22 from O'Hare Intl. to Logan Intl., returning Mon, Jul 28, priced at $165 found 3 days ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$165 Roundtrip, found 1 day ago

$165

Roundtrip

found 1 day ago

Select United flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $165 found 1 day ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$167 Roundtrip, found 1 day ago

$167

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $167 found 1 day ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$172 Roundtrip, found 1 day ago

$172

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $172 found 1 day ago

Fri, Aug 1 - Tue, Aug 12

ORD

O'Hare Intl.

BOS

Logan Intl.

$173 Roundtrip, found 2 days ago

$173

Roundtrip

found 2 days ago

Select Delta flight, departing Fri, Aug 1 from O'Hare Intl. to Logan Intl., returning Tue, Aug 12, priced at $173 found 2 days ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$177 Roundtrip, found 1 day ago

$177

Roundtrip

found 1 day ago

Select United flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $177 found 1 day ago

Wed, Aug 6 - Mon, Aug 18

ORD

O'Hare Intl.

BOS

Logan Intl.

$177 Roundtrip, found 6 days ago

$177

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Wed, Aug 6 from O'Hare Intl. to Logan Intl., returning Mon, Aug 18, priced at $177 found 6 days ago

Sat, Sep 6 - Sat, Oct 4

ORD

O'Hare Intl.

BOS

Logan Intl.

$179 Roundtrip, found 2 days ago

$179

Roundtrip

found 2 days ago

Select United flight, departing Sat, Sep 6 from O'Hare Intl. to Logan Intl., returning Sat, Oct 4, priced at $179 found 2 days ago

Sat, Aug 9 - Sat, Aug 16

ORD

O'Hare Intl.

BOS

Logan Intl.

$298 Roundtrip, found 6 days ago

$298

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Sat, Aug 9 from O'Hare Intl. to Logan Intl., returning Sat, Aug 16, priced at $298 found 6 days ago