Flights from Chicago to Lakeville

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.

Mon, Sep 15 - Mon, Sep 22

ORD

O'Hare Intl.

BOS

Logan Intl.

$91 Roundtrip, found 1 hour ago

$91

Roundtrip

found 1 hour ago

Select American Airlines flight, departing Mon, Sep 15 from O'Hare Intl. to Logan Intl., returning Mon, Sep 22, priced at $91 found 1 hour ago

Mon, Sep 15 - Mon, Sep 22

ORD

O'Hare Intl.

BOS

Logan Intl.

$114 Roundtrip, found 1 hour ago

$114

Roundtrip

found 1 hour ago

Select American Airlines flight, departing Mon, Sep 15 from O'Hare Intl. to Logan Intl., returning Mon, Sep 22, priced at $114 found 1 hour ago

Mon, Sep 15 - Mon, Sep 22

ORD

O'Hare Intl.

BOS

Logan Intl.

$127 Roundtrip, found 1 hour ago

$127

Roundtrip

found 1 hour ago

Select United flight, departing Mon, Sep 15 from O'Hare Intl. to Logan Intl., returning Mon, Sep 22, priced at $127 found 1 hour ago

Tue, Oct 21 - Tue, Oct 21

ORD

O'Hare Intl.

BOS

Logan Intl.

$132 Roundtrip, found 5 days ago

$132

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Tue, Oct 21 from O'Hare Intl. to Logan Intl., returning Tue, Oct 21, priced at $132 found 5 days ago

Mon, Sep 15 - Mon, Sep 22

ORD

O'Hare Intl.

BOS

Logan Intl.

$132 Roundtrip, found 1 hour ago

$132

Roundtrip

found 1 hour ago

Select Delta flight, departing Mon, Sep 15 from O'Hare Intl. to Logan Intl., returning Mon, Sep 22, priced at $132 found 1 hour ago

Mon, Sep 15 - Mon, Sep 22

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 1 hour ago

$137

Roundtrip

found 1 hour ago

Select United flight, departing Mon, Sep 15 from O'Hare Intl. to Logan Intl., returning Mon, Sep 22, priced at $137 found 1 hour ago

Sat, Sep 13 - Sat, Sep 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 1 hour ago

$137

Roundtrip

found 1 hour ago

Select Delta flight, departing Sat, Sep 13 from O'Hare Intl. to Logan Intl., returning Sat, Sep 20, priced at $137 found 1 hour 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

Mon, Sep 15 - Mon, Sep 22

ORD

O'Hare Intl.

BOS

Logan Intl.

$142 Roundtrip, found 1 hour ago

$142

Roundtrip

found 1 hour ago

Select United flight, departing Mon, Sep 15 from O'Hare Intl. to Logan Intl., returning Mon, Sep 22, priced at $142 found 1 hour ago

Mon, Sep 15 - Mon, Sep 22

ORD

O'Hare Intl.

BOS

Logan Intl.

$144 Roundtrip, found 1 hour ago

$144

Roundtrip

found 1 hour ago

Select Delta flight, departing Mon, Sep 15 from O'Hare Intl. to Logan Intl., returning Mon, Sep 22, priced at $144 found 1 hour ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$145 Roundtrip, found 1 day ago

$145

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 $145 found 1 day ago

Tue, Aug 5 - Thu, Aug 14

ORD

O'Hare Intl.

BOS

Logan Intl.

$148 Roundtrip, found 4 days ago

$148

Roundtrip

found 4 days ago

Select United flight, departing Tue, Aug 5 from O'Hare Intl. to Logan Intl., returning Thu, Aug 14, priced at $148 found 4 days ago

Mon, Sep 15 - Mon, Sep 22

ORD

O'Hare Intl.

BOS

Logan Intl.

$149 Roundtrip, found 1 hour ago

$149

Roundtrip

found 1 hour ago

Select United flight, departing Mon, Sep 15 from O'Hare Intl. to Logan Intl., returning Mon, Sep 22, priced at $149 found 1 hour ago

Mon, Sep 15 - Mon, Sep 22

ORD

O'Hare Intl.

BOS

Logan Intl.

$150 Roundtrip, found 1 hour ago

$150

Roundtrip

found 1 hour ago

Select United flight, departing Mon, Sep 15 from O'Hare Intl. to Logan Intl., returning Mon, Sep 22, priced at $150 found 1 hour ago

Mon, Sep 15 - Mon, Sep 22

ORD

O'Hare Intl.

BOS

Logan Intl.

$152 Roundtrip, found 1 hour ago

$152

Roundtrip

found 1 hour ago

Select United flight, departing Mon, Sep 15 from O'Hare Intl. to Logan Intl., returning Mon, Sep 22, priced at $152 found 1 hour ago

Tue, Aug 5 - Fri, Aug 8

ORD

O'Hare Intl.

BOS

Logan Intl.

$155 Roundtrip, found 1 day ago

$155

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Aug 5 from O'Hare Intl. to Logan Intl., returning Fri, Aug 8, priced at $155 found 1 day ago

Mon, Sep 15 - Mon, Sep 22

ORD

O'Hare Intl.

BOS

Logan Intl.

$155 Roundtrip, found 1 hour ago

$155

Roundtrip

found 1 hour ago

Select United flight, departing Mon, Sep 15 from O'Hare Intl. to Logan Intl., returning Mon, Sep 22, priced at $155 found 1 hour ago

Tue, Aug 5 - Tue, Aug 12

ORD

O'Hare Intl.

PVD

T.F. Green

$217 Roundtrip, found 1 day ago

$217

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Aug 5 from O'Hare Intl. to T.F. Green, returning Tue, Aug 12, priced at $217 found 1 day ago

Sun, Aug 3 - Wed, Aug 13

MDW

Midway Intl.

PVD

T.F. Green

$298 Roundtrip, found 1 day ago

$298

Roundtrip

found 1 day ago

Select Delta flight, departing Sun, Aug 3 from Midway Intl. to T.F. Green, returning Wed, Aug 13, priced at $298 found 1 day ago

Tue, Aug 5 - Thu, Aug 14

MDW

Midway Intl.

BOS

Logan Intl.

$319 Roundtrip, found 4 days ago

$319

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Aug 5 from Midway Intl. to Logan Intl., returning Thu, Aug 14, priced at $319 found 4 days ago