Flights from Boston to Historic Route 66

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, Nov 4 - Thu, Nov 6

BOS

Logan Intl.

ORD

O'Hare Intl.

$137 Roundtrip, found 20 hours ago

$137

Roundtrip

found 20 hours ago

Select United flight, departing Tue, Nov 4 from Logan Intl. to O'Hare Intl., returning Thu, Nov 6, priced at $137 found 20 hours ago

Tue, Nov 4 - Thu, Nov 6

BOS

Logan Intl.

ORD

O'Hare Intl.

$137 Roundtrip, found 20 hours ago

$137

Roundtrip

found 20 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 20 hours ago

Tue, Nov 4 - Thu, Nov 6

BOS

Logan Intl.

ORD

O'Hare Intl.

$139 Roundtrip, found 20 hours ago

$139

Roundtrip

found 20 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 20 hours ago

Tue, Nov 4 - Thu, Nov 6

BOS

Logan Intl.

ORD

O'Hare Intl.

$142 Roundtrip, found 20 hours ago

$142

Roundtrip

found 20 hours ago

Select Delta flight, departing Tue, Nov 4 from Logan Intl. to O'Hare Intl., returning Thu, Nov 6, priced at $142 found 20 hours ago

Tue, Nov 4 - Thu, Nov 6

BOS

Logan Intl.

ORD

O'Hare Intl.

$147 Roundtrip, found 20 hours ago

$147

Roundtrip

found 20 hours ago

Select Delta flight, departing Tue, Nov 4 from Logan Intl. to O'Hare Intl., returning Thu, Nov 6, priced at $147 found 20 hours ago

Tue, Nov 4 - Thu, Nov 6

BOS

Logan Intl.

ORD

O'Hare Intl.

$149 Roundtrip, found 20 hours ago

$149

Roundtrip

found 20 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 20 hours ago

Tue, Nov 4 - Thu, Nov 6

BOS

Logan Intl.

ORD

O'Hare Intl.

$153 Roundtrip, found 21 hours ago

$153

Roundtrip

found 21 hours ago

Select United flight, departing Tue, Nov 4 from Logan Intl. to O'Hare Intl., returning Thu, Nov 6, priced at $153 found 21 hours ago

Tue, Nov 4 - Thu, Nov 6

BOS

Logan Intl.

ORD

O'Hare Intl.

$154 Roundtrip, found 20 hours ago

$154

Roundtrip

found 20 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 20 hours ago

Tue, Nov 4 - Thu, Nov 6

BOS

Logan Intl.

ORD

O'Hare Intl.

$155 Roundtrip, found 20 hours ago

$155

Roundtrip

found 20 hours ago

Select United flight, departing Tue, Nov 4 from Logan Intl. to O'Hare Intl., returning Thu, Nov 6, priced at $155 found 20 hours ago

Sun, Dec 7 - Sat, Dec 13

BOS

Logan Intl.

ORD

O'Hare Intl.

$160 Roundtrip, found 2 days ago

$160

Roundtrip

found 2 days ago

Select United flight, departing Sun, Dec 7 from Logan Intl. to O'Hare Intl., returning Sat, Dec 13, priced at $160 found 2 days ago

Tue, Nov 4 - Thu, Nov 6

BOS

Logan Intl.

ORD

O'Hare Intl.

$165 Roundtrip, found 20 hours ago

$165

Roundtrip

found 20 hours ago

Select United flight, departing Tue, Nov 4 from Logan Intl. to O'Hare Intl., returning Thu, Nov 6, priced at $165 found 20 hours ago

Tue, Nov 4 - Thu, Nov 6

BOS

Logan Intl.

ORD

O'Hare Intl.

$167 Roundtrip, found 20 hours ago

$167

Roundtrip

found 20 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 20 hours ago

Tue, Nov 4 - Thu, Nov 6

BOS

Logan Intl.

ORD

O'Hare Intl.

$172 Roundtrip, found 20 hours ago

$172

Roundtrip

found 20 hours ago

Select United flight, departing Tue, Nov 4 from Logan Intl. to O'Hare Intl., returning Thu, Nov 6, priced at $172 found 20 hours ago

Tue, Nov 4 - Thu, Nov 6

BOS

Logan Intl.

ORD

O'Hare Intl.

$227 Roundtrip, found 20 hours ago

$227

Roundtrip

found 20 hours ago

Select JetBlue Airways flight, departing Tue, Nov 4 from Logan Intl. to O'Hare Intl., returning Thu, Nov 6, priced at $227 found 20 hours ago

Tue, Nov 4 - Thu, Nov 6

PVD

T.F. Green

ORD

O'Hare Intl.

$234 Roundtrip, found 1 day ago

$234

Roundtrip

found 1 day 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 1 day ago

Wed, Sep 17 - Wed, Sep 24

MHT

Manchester-Boston Regional

STL

Lambert-St. Louis Intl.

$237 Roundtrip, found 3 days ago

$237

Roundtrip

found 3 days ago

Select American Airlines flight, departing Wed, Sep 17 from Manchester-Boston Regional to Lambert-St. Louis Intl., returning Wed, Sep 24, priced at $237 found 3 days ago

Sat, Aug 2 - Thu, Aug 7

BOS

Logan Intl.

STL

Lambert-St. Louis Intl.

$278 Roundtrip, found 6 days ago

$278

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Sat, Aug 2 from Logan Intl. to Lambert-St. Louis Intl., returning Thu, Aug 7, priced at $278 found 6 days ago

Fri, Aug 15 - Mon, Aug 18

MHT

Manchester-Boston Regional

SGF

Springfield-Branson National

$349 Roundtrip, found 6 days ago

$349

Roundtrip

found 6 days ago

Select American Airlines flight, departing Fri, Aug 15 from Manchester-Boston Regional to Springfield-Branson National, returning Mon, Aug 18, priced at $349 found 6 days ago

Sat, Oct 4 - Sun, Oct 12

MHT

Manchester-Boston Regional

OKC

Will Rogers World

$352 Roundtrip, found 1 day ago

$352

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sat, Oct 4 from Manchester-Boston Regional to Will Rogers World, returning Sun, Oct 12, priced at $352 found 1 day ago

Tue, Sep 16 - Wed, Sep 17

BOS

Logan Intl.

FLG

Flagstaff Pulliam Field

$486 Roundtrip, found 4 days ago

$486

Roundtrip

found 4 days ago

Select American Airlines flight, departing Tue, Sep 16 from Logan Intl. to Flagstaff Pulliam Field, returning Wed, Sep 17, priced at $486 found 4 days ago