Flights from Boston to Grayslake

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.

Thu, Aug 21 - Mon, Aug 25

BOS

Logan Intl.

ORD

O'Hare Intl.

$121 Roundtrip, found 4 days ago

$121

Roundtrip

found 4 days ago

Select United flight, departing Thu, Aug 21 from Logan Intl. to O'Hare Intl., returning Mon, Aug 25, priced at $121 found 4 days ago

Thu, Aug 21 - Mon, Aug 25

BOS

Logan Intl.

ORD

O'Hare Intl.

$129 Roundtrip, found 4 days ago

$129

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Thu, Aug 21 from Logan Intl. to O'Hare Intl., returning Mon, Aug 25, priced at $129 found 4 days ago

Mon, Aug 18 - Wed, Aug 20

BOS

Logan Intl.

ORD

O'Hare Intl.

$136 Roundtrip, found 4 days ago

$136

Roundtrip

found 4 days ago

Select Delta flight, departing Mon, Aug 18 from Logan Intl. to O'Hare Intl., returning Wed, Aug 20, priced at $136 found 4 days ago

Tue, Aug 19 - Tue, Aug 26

BOS

Logan Intl.

ORD

O'Hare Intl.

$137 Roundtrip, found 4 days ago

$137

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Tue, Aug 19 from Logan Intl. to O'Hare Intl., returning Tue, Aug 26, priced at $137 found 4 days ago

Tue, Aug 19 - Tue, Aug 19

BOS

Logan Intl.

ORD

O'Hare Intl.

$137 Roundtrip, found 4 days ago

$137

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Aug 19 from Logan Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $137 found 4 days ago

Thu, Aug 21 - Mon, Aug 25

BOS

Logan Intl.

ORD

O'Hare Intl.

$139 Roundtrip, found 4 days ago

$139

Roundtrip

found 4 days ago

Select Delta flight, departing Thu, Aug 21 from Logan Intl. to O'Hare Intl., returning Mon, Aug 25, priced at $139 found 4 days ago

Mon, Aug 18 - Tue, Aug 26

BOS

Logan Intl.

ORD

O'Hare Intl.

$147 Roundtrip, found 4 days ago

$147

Roundtrip

found 4 days ago

Select Delta flight, departing Mon, Aug 18 from Logan Intl. to O'Hare Intl., returning Tue, Aug 26, priced at $147 found 4 days ago

Thu, Aug 21 - Mon, Aug 25

BOS

Logan Intl.

ORD

O'Hare Intl.

$156 Roundtrip, found 4 days ago

$156

Roundtrip

found 4 days ago

Select American Airlines flight, departing Thu, Aug 21 from Logan Intl. to O'Hare Intl., returning Mon, Aug 25, priced at $156 found 4 days ago

Mon, Aug 18 - Wed, Aug 20

BOS

Logan Intl.

ORD

O'Hare Intl.

$157 Roundtrip, found 4 days ago

$157

Roundtrip

found 4 days ago

Select Delta flight, departing Mon, Aug 18 from Logan Intl. to O'Hare Intl., returning Wed, Aug 20, priced at $157 found 4 days ago

Thu, Aug 21 - Mon, Aug 25

BOS

Logan Intl.

ORD

O'Hare Intl.

$157 Roundtrip, found 4 days ago

$157

Roundtrip

found 4 days ago

Select American Airlines flight, departing Thu, Aug 21 from Logan Intl. to O'Hare Intl., returning Mon, Aug 25, priced at $157 found 4 days ago

Thu, Aug 21 - Mon, Aug 25

BOS

Logan Intl.

ORD

O'Hare Intl.

$159 Roundtrip, found 4 days ago

$159

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Thu, Aug 21 from Logan Intl. to O'Hare Intl., returning Mon, Aug 25, priced at $159 found 4 days ago

Thu, Aug 21 - Mon, Aug 25

BOS

Logan Intl.

ORD

O'Hare Intl.

$167 Roundtrip, found 4 days ago

$167

Roundtrip

found 4 days ago

Select United flight, departing Thu, Aug 21 from Logan Intl. to O'Hare Intl., returning Mon, Aug 25, priced at $167 found 4 days ago

Mon, Aug 18 - Wed, Aug 20

BOS

Logan Intl.

ORD

O'Hare Intl.

$171 Roundtrip, found 4 days ago

$171

Roundtrip

found 4 days ago

Select Delta flight, departing Mon, Aug 18 from Logan Intl. to O'Hare Intl., returning Wed, Aug 20, priced at $171 found 4 days ago

Mon, Aug 18 - Wed, Aug 20

BOS

Logan Intl.

ORD

O'Hare Intl.

$173 Roundtrip, found 4 days ago

$173

Roundtrip

found 4 days ago

Select American Airlines flight, departing Mon, Aug 18 from Logan Intl. to O'Hare Intl., returning Wed, Aug 20, priced at $173 found 4 days ago

Mon, Aug 18 - Wed, Aug 20

BOS

Logan Intl.

ORD

O'Hare Intl.

$174 Roundtrip, found 4 days ago

$174

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Mon, Aug 18 from Logan Intl. to O'Hare Intl., returning Wed, Aug 20, priced at $174 found 4 days ago

Mon, Aug 18 - Wed, Aug 20

BOS

Logan Intl.

ORD

O'Hare Intl.

$176 Roundtrip, found 4 days ago

$176

Roundtrip

found 4 days ago

Select American Airlines flight, departing Mon, Aug 18 from Logan Intl. to O'Hare Intl., returning Wed, Aug 20, priced at $176 found 4 days ago

Tue, Aug 12 - Tue, Aug 19

BOS

Logan Intl.

ORD

O'Hare Intl.

$178 Roundtrip, found 4 days ago

$178

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Aug 12 from Logan Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $178 found 4 days ago

Mon, Aug 18 - Wed, Aug 20

BOS

Logan Intl.

ORD

O'Hare Intl.

$179 Roundtrip, found 4 days ago

$179

Roundtrip

found 4 days ago

Select United flight, departing Mon, Aug 18 from Logan Intl. to O'Hare Intl., returning Wed, Aug 20, priced at $179 found 4 days ago

Wed, Aug 13 - Wed, Aug 13

MHT

Manchester-Boston Regional

ORD

O'Hare Intl.

$206 Roundtrip, found 4 days ago

$206

Roundtrip

found 4 days ago

Select American Airlines flight, departing Wed, Aug 13 from Manchester-Boston Regional to O'Hare Intl., returning Wed, Aug 13, priced at $206 found 4 days ago

Sat, Aug 16 - Sat, Aug 23

BOS

Logan Intl.

ORD

O'Hare Intl.

$208 Roundtrip, found 4 days ago

$208

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Sat, Aug 16 from Logan Intl. to O'Hare Intl., returning Sat, Aug 23, priced at $208 found 4 days ago