Flights from Chicago to North Andover

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.

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 1 day ago

$137

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 $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 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.

$137 Roundtrip, found 1 day ago

$137

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, 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 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$145 Roundtrip, found 1 day ago

$145

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 $145 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

Tue, Aug 5 - Fri, Aug 8

ORD

O'Hare Intl.

BOS

Logan Intl.

$155 Roundtrip, found 4 days ago

$155

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Tue, Aug 5 from O'Hare Intl. to Logan Intl., returning Fri, Aug 8, priced at $155 found 4 days ago

Tue, Aug 5 - Tue, Aug 12

ORD

O'Hare Intl.

BOS

Logan Intl.

$155 Roundtrip, found 4 days ago

$155

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Aug 5 from O'Hare Intl. to Logan Intl., returning Tue, Aug 12, priced at $155 found 4 days ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$165 Roundtrip, found 1 day ago

$165

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 $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

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$172 Roundtrip, found 1 day ago

$172

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 $172 found 1 day ago

Sat, Aug 9 - Tue, Aug 12

ORD

O'Hare Intl.

BOS

Logan Intl.

$173 Roundtrip, found 4 days ago

$173

Roundtrip

found 4 days ago

Select Delta flight, departing Sat, Aug 9 from O'Hare Intl. to Logan Intl., returning Tue, Aug 12, priced at $173 found 4 days ago

Thu, Aug 7 - Wed, Aug 13

ORD

O'Hare Intl.

BOS

Logan Intl.

$175 Roundtrip, found 4 days ago

$175

Roundtrip

found 4 days ago

Select Delta flight, departing Thu, Aug 7 from O'Hare Intl. to Logan Intl., returning Wed, Aug 13, priced at $175 found 4 days ago

Thu, Aug 7 - Sun, Aug 10

ORD

O'Hare Intl.

BOS

Logan Intl.

$176 Roundtrip, found 4 days ago

$176

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Thu, Aug 7 from O'Hare Intl. to Logan Intl., returning Sun, Aug 10, priced at $176 found 4 days ago

Sat, Aug 9 - Mon, Aug 11

ORD

O'Hare Intl.

BOS

Logan Intl.

$177 Roundtrip, found 4 days ago

$177

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Sat, Aug 9 from O'Hare Intl. to Logan Intl., returning Mon, Aug 11, priced at $177 found 4 days ago

Fri, Oct 17 - Fri, Oct 17

ORD

O'Hare Intl.

BOS

Logan Intl.

$182 Roundtrip, found 3 days ago

$182

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Fri, Oct 17 from O'Hare Intl. to Logan Intl., returning Fri, Oct 17, priced at $182 found 3 days ago

Wed, Aug 6 - Sun, Aug 10

ORD

O'Hare Intl.

BOS

Logan Intl.

$182 Roundtrip, found 4 days ago

$182

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Wed, Aug 6 from O'Hare Intl. to Logan Intl., returning Sun, Aug 10, priced at $182 found 4 days ago

Mon, Jul 28 - Tue, Aug 5

ORD

O'Hare Intl.

MHT

Manchester-Boston Regional

$236 Roundtrip, found 4 days ago

$236

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Mon, Jul 28 from O'Hare Intl. to Manchester-Boston Regional, returning Tue, Aug 5, priced at $236 found 4 days ago

Thu, Jul 10 - Sat, Jul 19

MDW

Midway Intl.

BOS

Logan Intl.

$284 Roundtrip, found 3 days ago

$284

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Thu, Jul 10 from Midway Intl. to Logan Intl., returning Sat, Jul 19, priced at $284 found 3 days ago