Flights from Chicago to Madison

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 8 - Tue, Sep 16

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$193 Roundtrip, found 3 days ago

$193

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Mon, Sep 8 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Sep 16, priced at $193 found 3 days ago

Sun, Sep 7 - Tue, Sep 16

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$208 Roundtrip, found 3 days ago

$208

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Sun, Sep 7 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Sep 16, priced at $208 found 3 days ago

Mon, Sep 8 - Mon, Sep 15

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$210 Roundtrip, found 3 days ago

$210

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Mon, Sep 8 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 15, priced at $210 found 3 days ago

Tue, Jul 15 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$220 Roundtrip, just found

$220

Roundtrip

just found

Select JetBlue Airways flight, departing Tue, Jul 15 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $220 just found

Sun, Sep 7 - Mon, Sep 15

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$225 Roundtrip, found 3 days ago

$225

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Sun, Sep 7 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 15, priced at $225 found 3 days ago

Thu, Sep 11 - Mon, Sep 15

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$237 Roundtrip, found 3 days ago

$237

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Thu, Sep 11 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 15, priced at $237 found 3 days ago

Fri, Sep 12 - Tue, Sep 16

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$243 Roundtrip, found 3 days ago

$243

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Fri, Sep 12 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Sep 16, priced at $243 found 3 days ago

Mon, Sep 8 - Sat, Sep 13

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$243 Roundtrip, found 3 days ago

$243

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Mon, Sep 8 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Sep 13, priced at $243 found 3 days ago

Wed, Jul 16 - Mon, Jul 21

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$248 Roundtrip, just found

$248

Roundtrip

just found

Select JetBlue Airways flight, departing Wed, Jul 16 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Jul 21, priced at $248 just found

Sat, Sep 6 - Tue, Sep 16

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$253 Roundtrip, found 3 days ago

$253

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Sat, Sep 6 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Sep 16, priced at $253 found 3 days ago

Sun, Sep 7 - Sat, Sep 13

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$258 Roundtrip, found 3 days ago

$258

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Sun, Sep 7 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Sep 13, priced at $258 found 3 days ago

Wed, Jul 16 - Mon, Jul 21

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$259 Roundtrip, just found

$259

Roundtrip

just found

Select United flight, departing Wed, Jul 16 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Jul 21, priced at $259 just found

Wed, Jul 16 - Mon, Jul 21

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$269 Roundtrip, just found

$269

Roundtrip

just found

Select American Airlines flight, departing Wed, Jul 16 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Jul 21, priced at $269 just found

Mon, Jul 14 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$275 Roundtrip, just found

$275

Roundtrip

just found

Select JetBlue Airways flight, departing Mon, Jul 14 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $275 just found

Wed, Sep 10 - Fri, Sep 19

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$279 Roundtrip, found 3 days ago

$279

Roundtrip

found 3 days ago

Select Delta flight, departing Wed, Sep 10 from Midway Intl. to Portland Intl. Jetport, returning Fri, Sep 19, priced at $279 found 3 days ago

Mon, Jul 14 - Fri, Jul 18

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$279 Roundtrip, just found

$279

Roundtrip

just found

Select Delta flight, departing Mon, Jul 14 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Jul 18, priced at $279 just found

Sun, Jul 13 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$279 Roundtrip, just found

$279

Roundtrip

just found

Select JetBlue Airways flight, departing Sun, Jul 13 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $279 just found

Thu, Sep 11 - Sat, Sep 13

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$280 Roundtrip, found 3 days ago

$280

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Thu, Sep 11 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Sep 13, priced at $280 found 3 days ago

Wed, Jul 16 - Mon, Jul 21

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$288 Roundtrip, just found

$288

Roundtrip

just found

Select JetBlue Airways flight, departing Wed, Jul 16 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Jul 21, priced at $288 just found

Tue, Jul 29 - Sat, Aug 2

ORD

O'Hare Intl.

MHT

Manchester-Boston Regional

$303 Roundtrip, found 4 days ago

$303

Roundtrip

found 4 days 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 4 days ago