Flights from Chicago to Glen Mills

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.

$129 Roundtrip, found 3 hours ago

$129

Roundtrip

found 3 hours ago

Select Spirit Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $129 found 3 hours ago

Wed, Oct 15 - Tue, Oct 21

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 3 hours ago

$137

Roundtrip

found 3 hours ago

Select Delta flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Tue, Oct 21, priced at $137 found 3 hours ago

Tue, Sep 2 - Sat, Sep 6

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 2 days ago

$137

Roundtrip

found 2 days ago

Select United flight, departing Tue, Sep 2 from O'Hare Intl. to Logan Intl., returning Sat, Sep 6, priced at $137 found 2 days ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 3 hours ago

$137

Roundtrip

found 3 hours ago

Select JetBlue Airways flight, departing Thu, Oct 16 from O'Hare Intl. to Logan Intl., returning Tue, Oct 21, priced at $137 found 3 hours ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 3 hours ago

$137

Roundtrip

found 3 hours ago

Select American Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $137 found 3 hours ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$139 Roundtrip, found 3 hours ago

$139

Roundtrip

found 3 hours ago

Select Spirit Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $139 found 3 hours ago

Tue, Sep 23 - Wed, Oct 1

ORD

O'Hare Intl.

BOS

Logan Intl.

$140 Roundtrip, found 5 days ago

$140

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Tue, Sep 23 from O'Hare Intl. to Logan Intl., returning Wed, Oct 1, priced at $140 found 5 days ago

Tue, Sep 23 - Wed, Oct 1

ORD

O'Hare Intl.

BOS

Logan Intl.

$143 Roundtrip, found 5 days ago

$143

Roundtrip

found 5 days ago

Select United flight, departing Tue, Sep 23 from O'Hare Intl. to Logan Intl., returning Wed, Oct 1, priced at $143 found 5 days ago

Thu, Jun 12 - Mon, Jun 16

ORD

O'Hare Intl.

BOS

Logan Intl.

$150 Roundtrip, found 4 days ago

$150

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Thu, Jun 12 from O'Hare Intl. to Logan Intl., returning Mon, Jun 16, priced at $150 found 4 days ago

Wed, Aug 6 - Sun, Aug 10

ORD

O'Hare Intl.

BOS

Logan Intl.

$150 Roundtrip, found 5 days ago

$150

Roundtrip

found 5 days ago

Select United flight, departing Wed, Aug 6 from O'Hare Intl. to Logan Intl., returning Sun, Aug 10, priced at $150 found 5 days ago

Thu, Jun 12 - Fri, Jun 13

ORD

O'Hare Intl.

BOS

Logan Intl.

$151 Roundtrip, found 4 days ago

$151

Roundtrip

found 4 days ago

Select United flight, departing Thu, Jun 12 from O'Hare Intl. to Logan Intl., returning Fri, Jun 13, priced at $151 found 4 days ago

Wed, Oct 15 - Sun, Oct 19

ORD

O'Hare Intl.

BOS

Logan Intl.

$154 Roundtrip, found 4 days ago

$154

Roundtrip

found 4 days ago

Select United flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Sun, Oct 19, priced at $154 found 4 days ago

Thu, Jun 12 - Mon, Jun 16

ORD

O'Hare Intl.

BOS

Logan Intl.

$155 Roundtrip, found 4 days ago

$155

Roundtrip

found 4 days ago

Select United flight, departing Thu, Jun 12 from O'Hare Intl. to Logan Intl., returning Mon, Jun 16, priced at $155 found 4 days ago

Thu, Jun 12 - Mon, Jun 16

ORD

O'Hare Intl.

BOS

Logan Intl.

$162 Roundtrip, found 4 days ago

$162

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Thu, Jun 12 from O'Hare Intl. to Logan Intl., returning Mon, Jun 16, priced at $162 found 4 days ago

Sat, Aug 23 - Sun, Aug 24

ORD

O'Hare Intl.

BOS

Logan Intl.

$165 Roundtrip, found 1 day ago

$165

Roundtrip

found 1 day ago

Select United flight, departing Sat, Aug 23 from O'Hare Intl. to Logan Intl., returning Sun, Aug 24, priced at $165 found 1 day ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$167 Roundtrip, found 3 hours ago

$167

Roundtrip

found 3 hours ago

Select JetBlue Airways flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $167 found 3 hours ago

Sat, Jul 12 - Sat, Jul 19

ORD

O'Hare Intl.

BOS

Logan Intl.

$210 Roundtrip, found 23 hours ago

$210

Roundtrip

found 23 hours ago

Select Frontier Airlines flight, departing Sat, Jul 12 from O'Hare Intl. to Logan Intl., returning Sat, Jul 19, priced at $210 found 23 hours ago

Tue, Jul 29 - Sat, Aug 2

ORD

O'Hare Intl.

MHT

Manchester-Boston Regional

$303 Roundtrip, found 1 day ago

$303

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Tue, Jul 29 from O'Hare Intl. to Manchester-Boston Regional, returning Sat, Aug 2, priced at $303 found 1 day ago

Sat, Aug 23 - Sun, Aug 24

MDW

Midway Intl.

BOS

Logan Intl.

$318 Roundtrip, found 1 day ago

$318

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, Aug 23 from Midway Intl. to Logan Intl., returning Sun, Aug 24, priced at $318 found 1 day ago

Thu, Jun 12 - Mon, Jun 16

ORD

O'Hare Intl.

BOS

Logan Intl.

$1,112 Roundtrip, found 4 days ago

$1,112

Roundtrip

found 4 days ago

Select Alaska Airlines flight, departing Thu, Jun 12 from O'Hare Intl. to Logan Intl., returning Mon, Jun 16, priced at $1,112 found 4 days ago