Flights from Chicago to Middleton

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 21 - Tue, Oct 21

ORD

O'Hare Intl.

BOS

Logan Intl.

$132 Roundtrip, found 2 days ago

$132

Roundtrip

found 2 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 2 days ago

Tue, Aug 5 - Thu, Aug 14

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 1 day ago

$137

Roundtrip

found 1 day ago

Select United flight, departing Tue, Aug 5 from O'Hare Intl. to Logan Intl., returning Thu, Aug 14, priced at $137 found 1 day ago

Tue, Aug 5 - Wed, Aug 13

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 1 day ago

$137

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Aug 5 from O'Hare Intl. to Logan Intl., returning Wed, Aug 13, priced at $137 found 1 day ago

Tue, Aug 5 - Thu, Aug 14

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 1 day ago

$137

Roundtrip

found 1 day ago

Select American Airlines flight, departing Tue, Aug 5 from O'Hare Intl. to Logan Intl., returning Thu, Aug 14, priced at $137 found 1 day ago

Tue, Aug 5 - Thu, Aug 14

ORD

O'Hare Intl.

BOS

Logan Intl.

$139 Roundtrip, found 1 day ago

$139

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Aug 5 from O'Hare Intl. to Logan Intl., returning Thu, Aug 14, priced at $139 found 1 day ago

Wed, Oct 15 - Wed, Oct 15

ORD

O'Hare Intl.

BOS

Logan Intl.

$145 Roundtrip, found 2 days ago

$145

Roundtrip

found 2 days ago

Select Delta flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Wed, Oct 15, priced at $145 found 2 days ago

Tue, Aug 5 - Thu, Aug 14

ORD

O'Hare Intl.

BOS

Logan Intl.

$148 Roundtrip, found 1 day ago

$148

Roundtrip

found 1 day ago

Select United flight, departing Tue, Aug 5 from O'Hare Intl. to Logan Intl., returning Thu, Aug 14, priced at $148 found 1 day ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$153 Roundtrip, found 4 days ago

$153

Roundtrip

found 4 days ago

Select Delta flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $153 found 4 days ago

Tue, Aug 5 - Thu, Aug 14

ORD

O'Hare Intl.

BOS

Logan Intl.

$165 Roundtrip, found 1 day ago

$165

Roundtrip

found 1 day ago

Select United flight, departing Tue, Aug 5 from O'Hare Intl. to Logan Intl., returning Thu, Aug 14, priced at $165 found 1 day ago

Wed, Oct 15 - Sun, Oct 19

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 Sun, Oct 19, priced at $167 found 1 day ago

Tue, Aug 5 - Thu, Aug 14

ORD

O'Hare Intl.

BOS

Logan Intl.

$167 Roundtrip, found 1 day ago

$167

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Aug 5 from O'Hare Intl. to Logan Intl., returning Thu, Aug 14, priced at $167 found 1 day ago

Tue, Aug 5 - Thu, Aug 14

ORD

O'Hare Intl.

BOS

Logan Intl.

$172 Roundtrip, found 1 day ago

$172

Roundtrip

found 1 day ago

Select United flight, departing Tue, Aug 5 from O'Hare Intl. to Logan Intl., returning Thu, Aug 14, priced at $172 found 1 day ago

Wed, Oct 15 - Sun, Oct 19

ORD

O'Hare Intl.

BOS

Logan Intl.

$173 Roundtrip, found 1 day ago

$173

Roundtrip

found 1 day ago

Select Delta flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Sun, Oct 19, priced at $173 found 1 day ago

Tue, Aug 5 - Thu, Aug 14

ORD

O'Hare Intl.

BOS

Logan Intl.

$175 Roundtrip, found 1 day ago

$175

Roundtrip

found 1 day ago

Select United flight, departing Tue, Aug 5 from O'Hare Intl. to Logan Intl., returning Thu, Aug 14, priced at $175 found 1 day ago

Thu, Oct 23 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$175 Roundtrip, found 2 days ago

$175

Roundtrip

found 2 days ago

Select Delta flight, departing Thu, Oct 23 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $175 found 2 days ago

Tue, Aug 5 - Thu, Aug 14

ORD

O'Hare Intl.

BOS

Logan Intl.

$178 Roundtrip, found 1 day ago

$178

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Aug 5 from O'Hare Intl. to Logan Intl., returning Thu, Aug 14, priced at $178 found 1 day ago

Wed, Oct 15 - Fri, Oct 17

ORD

O'Hare Intl.

BOS

Logan Intl.

$179 Roundtrip, found 2 days ago

$179

Roundtrip

found 2 days ago

Select United flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Fri, Oct 17, priced at $179 found 2 days ago

Fri, Oct 17 - Fri, Oct 17

ORD

O'Hare Intl.

BOS

Logan Intl.

$182 Roundtrip, found 2 days ago

$182

Roundtrip

found 2 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 2 days ago

Sun, Oct 12 - Fri, Oct 24

ORD

O'Hare Intl.

BOS

Logan Intl.

$182 Roundtrip, found 2 days ago

$182

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Sun, Oct 12 from O'Hare Intl. to Logan Intl., returning Fri, Oct 24, priced at $182 found 2 days ago

Tue, Aug 5 - Thu, Aug 14

MDW

Midway Intl.

BOS

Logan Intl.

$319 Roundtrip, found 1 day ago

$319

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Aug 5 from Midway Intl. to Logan Intl., returning Thu, Aug 14, priced at $319 found 1 day ago