Flights from Chicago to Cumberland

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.

Thu, Oct 16 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$119 Roundtrip, found 6 days ago

$119

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $119 found 6 days ago

Thu, Oct 16 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$122 Roundtrip, found 6 days ago

$122

Roundtrip

found 6 days ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $122 found 6 days ago

Thu, Oct 16 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$125 Roundtrip, found 6 days ago

$125

Roundtrip

found 6 days ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $125 found 6 days ago

Wed, Oct 15 - Fri, Oct 17

ORD

O'Hare Intl.

BOS

Logan Intl.

$125 Roundtrip, found 1 day ago

$125

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Fri, Oct 17, priced at $125 found 1 day ago

Thu, Oct 16 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$128 Roundtrip, found 6 days ago

$128

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Thu, Oct 16 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $128 found 6 days ago

Sun, Oct 12 - Fri, Oct 17

ORD

O'Hare Intl.

BOS

Logan Intl.

$131 Roundtrip, found 1 day ago

$131

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Sun, Oct 12 from O'Hare Intl. to Logan Intl., returning Fri, Oct 17, priced at $131 found 1 day ago

Thu, Oct 16 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$136 Roundtrip, found 6 days ago

$136

Roundtrip

found 6 days ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $136 found 6 days ago

Sun, Oct 12 - Sat, Oct 18

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 1 day ago

$137

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Sun, Oct 12 from O'Hare Intl. to Logan Intl., returning Sat, Oct 18, priced at $137 found 1 day ago

Thu, Oct 16 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$139 Roundtrip, found 6 days ago

$139

Roundtrip

found 6 days ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $139 found 6 days ago

Thu, Oct 16 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$146 Roundtrip, found 6 days ago

$146

Roundtrip

found 6 days ago

Select American Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $146 found 6 days ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$149 Roundtrip, found 1 day ago

$149

Roundtrip

found 1 day ago

Select United flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $149 found 1 day ago

Wed, Oct 15 - Thu, Oct 16

ORD

O'Hare Intl.

BOS

Logan Intl.

$155 Roundtrip, found 1 day ago

$155

Roundtrip

found 1 day ago

Select Delta flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Thu, Oct 16, priced at $155 found 1 day ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$155 Roundtrip, found 1 day ago

$155

Roundtrip

found 1 day ago

Select American Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $155 found 1 day ago

Thu, Oct 16 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$156 Roundtrip, found 6 days ago

$156

Roundtrip

found 6 days ago

Select Delta flight, departing Thu, Oct 16 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $156 found 6 days ago

Thu, Oct 16 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$157 Roundtrip, found 6 days ago

$157

Roundtrip

found 6 days ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $157 found 6 days ago

Thu, Oct 16 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$158 Roundtrip, found 6 days ago

$158

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Thu, Oct 16 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $158 found 6 days ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$160 Roundtrip, found 1 day ago

$160

Roundtrip

found 1 day ago

Select Delta flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $160 found 1 day ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$163 Roundtrip, found 1 day ago

$163

Roundtrip

found 1 day ago

Select United flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $163 found 1 day ago

Tue, Aug 26 - Sat, Aug 30

ORD

O'Hare Intl.

PVD

T.F. Green

$266 Roundtrip, found 13 hours ago

$266

Roundtrip

found 13 hours ago

Select JetBlue Airways flight, departing Tue, Aug 26 from O'Hare Intl. to T.F. Green, returning Sat, Aug 30, priced at $266 found 13 hours ago

Thu, Jul 10 - Sat, Jul 19

MDW

Midway Intl.

BOS

Logan Intl.

$271 Roundtrip, found 1 day ago

$271

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Thu, Jul 10 from Midway Intl. to Logan Intl., returning Sat, Jul 19, priced at $271 found 1 day ago