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.

Sat, Oct 4 - Fri, Oct 10

ORD

O'Hare Intl.

MKL

McKellar-Sipes Regional

$194 Roundtrip, found 15 hours ago

$194

Roundtrip

found 15 hours ago

Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sat, Oct 4 from O'Hare Intl. to McKellar-Sipes Regional, returning Fri, Oct 10, priced at $194 found 15 hours ago

Thu, Jul 17 - Sun, Jul 20

ORD

O'Hare Intl.

MKL

McKellar-Sipes Regional

$199 Roundtrip, found 15 hours ago

$199

Roundtrip

found 15 hours ago

Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Jul 17 from O'Hare Intl. to McKellar-Sipes Regional, returning Sun, Jul 20, priced at $199 found 15 hours ago

Thu, Jul 17 - Thu, Jul 24

ORD

O'Hare Intl.

MKL

McKellar-Sipes Regional

$204 Roundtrip, found 15 hours ago

$204

Roundtrip

found 15 hours ago

Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Jul 17 from O'Hare Intl. to McKellar-Sipes Regional, returning Thu, Jul 24, priced at $204 found 15 hours ago

Mon, Jul 14 - Sun, Jul 20

ORD

O'Hare Intl.

MKL

McKellar-Sipes Regional

$219 Roundtrip, found 15 hours ago

$219

Roundtrip

found 15 hours ago

Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Mon, Jul 14 from O'Hare Intl. to McKellar-Sipes Regional, returning Sun, Jul 20, priced at $219 found 15 hours ago

Mon, Jul 14 - Thu, Jul 24

ORD

O'Hare Intl.

MKL

McKellar-Sipes Regional

$224 Roundtrip, found 15 hours ago

$224

Roundtrip

found 15 hours ago

Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Mon, Jul 14 from O'Hare Intl. to McKellar-Sipes Regional, returning Thu, Jul 24, priced at $224 found 15 hours ago

Thu, Jul 17 - Fri, Jul 18

ORD

O'Hare Intl.

MKL

McKellar-Sipes Regional

$244 Roundtrip, found 15 hours ago

$244

Roundtrip

found 15 hours ago

Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Jul 17 from O'Hare Intl. to McKellar-Sipes Regional, returning Fri, Jul 18, priced at $244 found 15 hours ago

Mon, Jul 14 - Sat, Jul 19

ORD

O'Hare Intl.

MKL

McKellar-Sipes Regional

$244 Roundtrip, found 15 hours ago

$244

Roundtrip

found 15 hours ago

Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Mon, Jul 14 from O'Hare Intl. to McKellar-Sipes Regional, returning Sat, Jul 19, priced at $244 found 15 hours ago

Mon, Jul 14 - Fri, Jul 18

ORD

O'Hare Intl.

MKL

McKellar-Sipes Regional

$264 Roundtrip, found 15 hours ago

$264

Roundtrip

found 15 hours ago

Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Mon, Jul 14 from O'Hare Intl. to McKellar-Sipes Regional, returning Fri, Jul 18, priced at $264 found 15 hours ago

Tue, Oct 7 - Fri, Oct 10

ORD

O'Hare Intl.

MKL

McKellar-Sipes Regional

$272 Roundtrip, found 15 hours ago

$272

Roundtrip

found 15 hours ago

Select Delta flight, departing Tue, Oct 7 from O'Hare Intl. to McKellar-Sipes Regional, returning Fri, Oct 10, priced at $272 found 15 hours ago

Thu, Jul 17 - Mon, Jul 21

ORD

O'Hare Intl.

MKL

McKellar-Sipes Regional

$319 Roundtrip, found 15 hours ago

$319

Roundtrip

found 15 hours ago

Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Jul 17 from O'Hare Intl. to McKellar-Sipes Regional, returning Mon, Jul 21, priced at $319 found 15 hours ago

Tue, Jul 15 - Sun, Jul 20

ORD

O'Hare Intl.

MKL

McKellar-Sipes Regional

$342 Roundtrip, found 15 hours ago

$342

Roundtrip

found 15 hours ago

Select Delta flight, departing Tue, Jul 15 from O'Hare Intl. to McKellar-Sipes Regional, returning Sun, Jul 20, priced at $342 found 15 hours ago

Tue, Jul 15 - Sat, Jul 19

ORD

O'Hare Intl.

MKL

McKellar-Sipes Regional

$352 Roundtrip, found 15 hours ago

$352

Roundtrip

found 15 hours ago

Select Delta flight, departing Tue, Jul 15 from O'Hare Intl. to McKellar-Sipes Regional, returning Sat, Jul 19, priced at $352 found 15 hours ago

Thu, Jul 17 - Mon, Jul 21

ORD

O'Hare Intl.

MKL

McKellar-Sipes Regional

$356 Roundtrip, found 15 hours ago

$356

Roundtrip

found 15 hours ago

Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Jul 17 from O'Hare Intl. to McKellar-Sipes Regional, returning Mon, Jul 21, priced at $356 found 15 hours ago

Thu, Jul 17 - Mon, Jul 21

ORD

O'Hare Intl.

MKL

McKellar-Sipes Regional

$362 Roundtrip, found 15 hours ago

$362

Roundtrip

found 15 hours ago

Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Jul 17 from O'Hare Intl. to McKellar-Sipes Regional, returning Mon, Jul 21, priced at $362 found 15 hours ago

Tue, Jul 15 - Fri, Jul 18

ORD

O'Hare Intl.

MKL

McKellar-Sipes Regional

$392 Roundtrip, found 15 hours ago

$392

Roundtrip

found 15 hours ago

Select Delta flight, departing Tue, Jul 15 from O'Hare Intl. to McKellar-Sipes Regional, returning Fri, Jul 18, priced at $392 found 15 hours ago

Thu, Jul 17 - Mon, Jul 21

ORD

O'Hare Intl.

MKL

McKellar-Sipes Regional

$417 Roundtrip, found 15 hours ago

$417

Roundtrip

found 15 hours ago

Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Jul 17 from O'Hare Intl. to McKellar-Sipes Regional, returning Mon, Jul 21, priced at $417 found 15 hours ago

Tue, Oct 7 - Mon, Oct 13

ORD

O'Hare Intl.

MKL

McKellar-Sipes Regional

$423 Roundtrip, found 15 hours ago

$423

Roundtrip

found 15 hours ago

Select Delta flight, departing Tue, Oct 7 from O'Hare Intl. to McKellar-Sipes Regional, returning Mon, Oct 13, priced at $423 found 15 hours ago

Tue, Oct 7 - Mon, Oct 13

ORD

O'Hare Intl.

MKL

McKellar-Sipes Regional

$475 Roundtrip, found 15 hours ago

$475

Roundtrip

found 15 hours ago

Select Delta flight, departing Tue, Oct 7 from O'Hare Intl. to McKellar-Sipes Regional, returning Mon, Oct 13, priced at $475 found 15 hours ago

Thu, Jul 17 - Mon, Jul 21

ORD

O'Hare Intl.

MKL

McKellar-Sipes Regional

$527 Roundtrip, found 15 hours ago

$527

Roundtrip

found 15 hours ago

Select Delta flight, departing Thu, Jul 17 from O'Hare Intl. to McKellar-Sipes Regional, returning Mon, Jul 21, priced at $527 found 15 hours ago

Thu, Jul 17 - Mon, Jul 21

ORD

O'Hare Intl.

MKL

McKellar-Sipes Regional

$685 Roundtrip, found 15 hours ago

$685

Roundtrip

found 15 hours ago

Select Delta flight, departing Thu, Jul 17 from O'Hare Intl. to McKellar-Sipes Regional, returning Mon, Jul 21, priced at $685 found 15 hours ago