Flights from Chicago to Milton

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.

Tue, Oct 7 - Wed, Oct 15

ORD

O'Hare Intl.

BOS

Logan Intl.

$91 Roundtrip, just found

$91

Roundtrip

just found

Select JetBlue Airways flight, departing Tue, Oct 7 from O'Hare Intl. to Logan Intl., returning Wed, Oct 15, priced at $91 just found

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$91 Roundtrip, found 20 hours ago

$91

Roundtrip

found 20 hours ago

Select American Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $91 found 20 hours ago

Fri, Sep 26 - Wed, Oct 1

ORD

O'Hare Intl.

BOS

Logan Intl.

$98 Roundtrip, just found

$98

Roundtrip

just found

Select JetBlue Airways flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Wed, Oct 1, priced at $98 just found

Fri, Sep 26 - Mon, Sep 29

ORD

O'Hare Intl.

BOS

Logan Intl.

$98 Roundtrip, just found

$98

Roundtrip

just found

Select United flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Mon, Sep 29, priced at $98 just found

Tue, Oct 7 - Thu, Oct 16

ORD

O'Hare Intl.

BOS

Logan Intl.

$114 Roundtrip, just found

$114

Roundtrip

just found

Select JetBlue Airways flight, departing Tue, Oct 7 from O'Hare Intl. to Logan Intl., returning Thu, Oct 16, priced at $114 just found

Fri, Sep 26 - Mon, Sep 29

ORD

O'Hare Intl.

BOS

Logan Intl.

$116 Roundtrip, just found

$116

Roundtrip

just found

Select United flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Mon, Sep 29, priced at $116 just found

Fri, Sep 26 - Mon, Sep 29

ORD

O'Hare Intl.

BOS

Logan Intl.

$120 Roundtrip, just found

$120

Roundtrip

just found

Select United flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Mon, Sep 29, priced at $120 just found

Fri, Sep 26 - Sun, Sep 28

ORD

O'Hare Intl.

BOS

Logan Intl.

$121 Roundtrip, just found

$121

Roundtrip

just found

Select JetBlue Airways flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Sun, Sep 28, priced at $121 just found

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$124 Roundtrip, found 20 hours ago

$124

Roundtrip

found 20 hours ago

Select Delta flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $124 found 20 hours ago

Fri, Sep 26 - Mon, Sep 29

ORD

O'Hare Intl.

BOS

Logan Intl.

$126 Roundtrip, just found

$126

Roundtrip

just found

Select United flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Mon, Sep 29, priced at $126 just found

Mon, Sep 15 - Mon, Sep 22

ORD

O'Hare Intl.

BOS

Logan Intl.

$127 Roundtrip, found 2 days ago

$127

Roundtrip

found 2 days ago

Select United flight, departing Mon, Sep 15 from O'Hare Intl. to Logan Intl., returning Mon, Sep 22, priced at $127 found 2 days ago

Fri, Sep 26 - Mon, Sep 29

ORD

O'Hare Intl.

BOS

Logan Intl.

$128 Roundtrip, just found

$128

Roundtrip

just found

Select United flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Mon, Sep 29, priced at $128 just found

Mon, Sep 15 - Mon, Sep 22

ORD

O'Hare Intl.

BOS

Logan Intl.

$132 Roundtrip, found 2 days ago

$132

Roundtrip

found 2 days ago

Select Delta flight, departing Mon, Sep 15 from O'Hare Intl. to Logan Intl., returning Mon, Sep 22, priced at $132 found 2 days ago

Fri, Sep 26 - Mon, Sep 29

ORD

O'Hare Intl.

BOS

Logan Intl.

$133 Roundtrip, just found

$133

Roundtrip

just found

Select United flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Mon, Sep 29, priced at $133 just found

Fri, Sep 26 - Mon, Sep 29

ORD

O'Hare Intl.

BOS

Logan Intl.

$135 Roundtrip, just found

$135

Roundtrip

just found

Select United flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Mon, Sep 29, priced at $135 just found

Thu, Oct 9 - Thu, Oct 16

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, just found

$137

Roundtrip

just found

Select JetBlue Airways flight, departing Thu, Oct 9 from O'Hare Intl. to Logan Intl., returning Thu, Oct 16, priced at $137 just found

Sat, Sep 27 - Sat, Sep 27

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, just found

$137

Roundtrip

just found

Select Delta flight, departing Sat, Sep 27 from O'Hare Intl. to Logan Intl., returning Sat, Sep 27, priced at $137 just found

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

Fri, Sep 26 - Mon, Sep 29

ORD

O'Hare Intl.

BOS

Logan Intl.

$281 Roundtrip, just found

$281

Roundtrip

just found

Select Frontier Airlines flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Mon, Sep 29, priced at $281 just found

Mon, Aug 4 - Tue, Aug 12

MDW

Midway Intl.

BOS

Logan Intl.

$368 Roundtrip, found 5 days ago

$368

Roundtrip

found 5 days ago

Select Delta flight, departing Mon, Aug 4 from Midway Intl. to Logan Intl., returning Tue, Aug 12, priced at $368 found 5 days ago