Flights from Chicago to Tewksbury

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, Aug 23 - Tue, Aug 26

ORD

O'Hare Intl.

BOS

Logan Intl.

$129 Roundtrip, found 3 days ago

$129

Roundtrip

found 3 days ago

Select United flight, departing Sat, Aug 23 from O'Hare Intl. to Logan Intl., returning Tue, Aug 26, priced at $129 found 3 days ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

BOS

Logan Intl.

$130 Roundtrip, found 5 days ago

$130

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Logan Intl., returning Tue, Oct 21, priced at $130 found 5 days ago

Fri, May 30 - Sun, Jun 1

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 2 days ago

$137

Roundtrip

found 2 days ago

Select American Airlines flight, departing Fri, May 30 from O'Hare Intl. to Logan Intl., returning Sun, Jun 1, priced at $137 found 2 days ago

Fri, May 30 - Sun, Jun 1

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 2 days ago

$137

Roundtrip

found 2 days ago

Select United flight, departing Fri, May 30 from O'Hare Intl. to Logan Intl., returning Sun, Jun 1, priced at $137 found 2 days ago

Thu, Aug 7 - Tue, Aug 12

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 8 hours ago

$137

Roundtrip

found 8 hours ago

Select JetBlue Airways flight, departing Thu, Aug 7 from O'Hare Intl. to Logan Intl., returning Tue, Aug 12, priced at $137 found 8 hours ago

Tue, Aug 5 - Wed, Aug 13

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 8 hours ago

$137

Roundtrip

found 8 hours ago

Select Delta flight, departing Tue, Aug 5 from O'Hare Intl. to Logan Intl., returning Wed, Aug 13, priced at $137 found 8 hours ago

Thu, Aug 7 - Mon, Aug 11

ORD

O'Hare Intl.

BOS

Logan Intl.

$143 Roundtrip, found 3 days ago

$143

Roundtrip

found 3 days ago

Select American Airlines flight, departing Thu, Aug 7 from O'Hare Intl. to Logan Intl., returning Mon, Aug 11, priced at $143 found 3 days ago

Tue, Oct 7 - Thu, Oct 16

ORD

O'Hare Intl.

BOS

Logan Intl.

$145 Roundtrip, found 1 day ago

$145

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Oct 7 from O'Hare Intl. to Logan Intl., returning Thu, Oct 16, priced at $145 found 1 day ago

Fri, Aug 8 - Fri, Aug 8

ORD

O'Hare Intl.

BOS

Logan Intl.

$150 Roundtrip, found 3 days ago

$150

Roundtrip

found 3 days ago

Select Delta flight, departing Fri, Aug 8 from O'Hare Intl. to Logan Intl., returning Fri, Aug 8, priced at $150 found 3 days ago

Fri, May 30 - Sun, Jun 1

ORD

O'Hare Intl.

BOS

Logan Intl.

$151 Roundtrip, found 2 days ago

$151

Roundtrip

found 2 days ago

Select United flight, departing Fri, May 30 from O'Hare Intl. to Logan Intl., returning Sun, Jun 1, priced at $151 found 2 days ago

Wed, Oct 15 - Sun, Oct 19

ORD

O'Hare Intl.

BOS

Logan Intl.

$155 Roundtrip, found 5 days ago

$155

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Sun, Oct 19, priced at $155 found 5 days ago

Tue, Aug 5 - Tue, Aug 12

ORD

O'Hare Intl.

BOS

Logan Intl.

$155 Roundtrip, found 8 hours ago

$155

Roundtrip

found 8 hours ago

Select Delta flight, departing Tue, Aug 5 from O'Hare Intl. to Logan Intl., returning Tue, Aug 12, priced at $155 found 8 hours ago

Sat, Aug 23 - Tue, Aug 26

ORD

O'Hare Intl.

BOS

Logan Intl.

$157 Roundtrip, found 3 days ago

$157

Roundtrip

found 3 days ago

Select United flight, departing Sat, Aug 23 from O'Hare Intl. to Logan Intl., returning Tue, Aug 26, priced at $157 found 3 days ago

Fri, May 30 - Sun, Jun 1

ORD

O'Hare Intl.

BOS

Logan Intl.

$158 Roundtrip, found 2 days ago

$158

Roundtrip

found 2 days ago

Select United flight, departing Fri, May 30 from O'Hare Intl. to Logan Intl., returning Sun, Jun 1, priced at $158 found 2 days ago

Fri, Aug 22 - Fri, Aug 22

ORD

O'Hare Intl.

BOS

Logan Intl.

$160 Roundtrip, found 1 day ago

$160

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Fri, Aug 22 from O'Hare Intl. to Logan Intl., returning Fri, Aug 22, priced at $160 found 1 day ago

Thu, Aug 7 - Mon, Aug 11

ORD

O'Hare Intl.

BOS

Logan Intl.

$161 Roundtrip, found 3 days ago

$161

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Thu, Aug 7 from O'Hare Intl. to Logan Intl., returning Mon, Aug 11, priced at $161 found 3 days ago

Wed, Oct 15 - Sun, Oct 19

ORD

O'Hare Intl.

BOS

Logan Intl.

$163 Roundtrip, found 5 days ago

$163

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Sun, Oct 19, priced at $163 found 5 days ago

Fri, May 30 - Sun, Jun 1

ORD

O'Hare Intl.

BOS

Logan Intl.

$164 Roundtrip, found 2 days ago

$164

Roundtrip

found 2 days ago

Select United flight, departing Fri, May 30 from O'Hare Intl. to Logan Intl., returning Sun, Jun 1, priced at $164 found 2 days ago

Mon, Aug 4 - Sat, Aug 9

ORD

O'Hare Intl.

BOS

Logan Intl.

$220 Roundtrip, found 8 hours ago

$220

Roundtrip

found 8 hours ago

Select Frontier Airlines flight, departing Mon, Aug 4 from O'Hare Intl. to Logan Intl., returning Sat, Aug 9, priced at $220 found 8 hours ago

Sat, Aug 23 - Tue, Aug 26

MDW

Midway Intl.

BOS

Logan Intl.

$313 Roundtrip, found 3 days ago

$313

Roundtrip

found 3 days ago

Select Delta flight, departing Sat, Aug 23 from Midway Intl. to Logan Intl., returning Tue, Aug 26, priced at $313 found 3 days ago