Flights from Chicago to Osceola

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.

Sun, Jun 8 - Sat, Jun 14

ORD

O'Hare Intl.

MSP

Minneapolis - St. Paul Intl.

$184 Roundtrip, found 1 day ago

$184

Roundtrip

found 1 day ago

Select Sun Country Airlines flight, departing Sun, Jun 8 from O'Hare Intl. to Minneapolis - St. Paul Intl., returning Sat, Jun 14, priced at $184 found 1 day ago

Sat, Jun 7 - Fri, Jun 13

ORD

O'Hare Intl.

MSP

Minneapolis - St. Paul Intl.

$195 Roundtrip, found 3 days ago

$195

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Sat, Jun 7 from O'Hare Intl. to Minneapolis - St. Paul Intl., returning Fri, Jun 13, priced at $195 found 3 days ago

Thu, Sep 11 - Mon, Sep 15

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$200 Roundtrip, found 1 day ago

$200

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Thu, Sep 11 from Midway Intl. to Minneapolis - St. Paul Intl., returning Mon, Sep 15, priced at $200 found 1 day ago

Sat, Jun 7 - Sat, Jun 14

ORD

O'Hare Intl.

MSP

Minneapolis - St. Paul Intl.

$204 Roundtrip, found 1 day ago

$204

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Sat, Jun 7 from O'Hare Intl. to Minneapolis - St. Paul Intl., returning Sat, Jun 14, priced at $204 found 1 day ago

Sun, Jun 8 - Sun, Jun 15

ORD

O'Hare Intl.

MSP

Minneapolis - St. Paul Intl.

$213 Roundtrip, found 1 day ago

$213

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Sun, Jun 8 from O'Hare Intl. to Minneapolis - St. Paul Intl., returning Sun, Jun 15, priced at $213 found 1 day ago

Sun, Jun 8 - Mon, Jun 9

ORD

O'Hare Intl.

MSP

Minneapolis - St. Paul Intl.

$214 Roundtrip, found 1 day ago

$214

Roundtrip

found 1 day ago

Select Sun Country Airlines flight, departing Sun, Jun 8 from O'Hare Intl. to Minneapolis - St. Paul Intl., returning Mon, Jun 9, priced at $214 found 1 day ago

Thu, Sep 11 - Mon, Sep 15

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$226 Roundtrip, found 1 day ago

$226

Roundtrip

found 1 day ago

Select Delta flight, departing Thu, Sep 11 from Midway Intl. to Minneapolis - St. Paul Intl., returning Mon, Sep 15, priced at $226 found 1 day ago

Mon, Jun 9 - Sat, Jun 14

ORD

O'Hare Intl.

MSP

Minneapolis - St. Paul Intl.

$234 Roundtrip, found 1 day ago

$234

Roundtrip

found 1 day ago

Select Sun Country Airlines flight, departing Mon, Jun 9 from O'Hare Intl. to Minneapolis - St. Paul Intl., returning Sat, Jun 14, priced at $234 found 1 day ago

Thu, Sep 11 - Mon, Sep 15

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$256 Roundtrip, found 1 day ago

$256

Roundtrip

found 1 day ago

Select Delta flight, departing Thu, Sep 11 from Midway Intl. to Minneapolis - St. Paul Intl., returning Mon, Sep 15, priced at $256 found 1 day ago

Mon, Jun 9 - Sun, Jun 15

ORD

O'Hare Intl.

MSP

Minneapolis - St. Paul Intl.

$267 Roundtrip, found 1 day ago

$267

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Mon, Jun 9 from O'Hare Intl. to Minneapolis - St. Paul Intl., returning Sun, Jun 15, priced at $267 found 1 day ago

Fri, Jun 6 - Sun, Jun 15

ORD

O'Hare Intl.

MSP

Minneapolis - St. Paul Intl.

$276 Roundtrip, found 1 day ago

$276

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Fri, Jun 6 from O'Hare Intl. to Minneapolis - St. Paul Intl., returning Sun, Jun 15, priced at $276 found 1 day ago

Sat, Jun 7 - Mon, Jun 9

ORD

O'Hare Intl.

MSP

Minneapolis - St. Paul Intl.

$285 Roundtrip, found 1 day ago

$285

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Sat, Jun 7 from O'Hare Intl. to Minneapolis - St. Paul Intl., returning Mon, Jun 9, priced at $285 found 1 day ago

Thu, Sep 11 - Mon, Sep 15

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$317 Roundtrip, found 1 day ago

$317

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Thu, Sep 11 from Midway Intl. to Minneapolis - St. Paul Intl., returning Mon, Sep 15, priced at $317 found 1 day ago

Thu, Sep 11 - Mon, Sep 15

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$323 Roundtrip, found 1 day ago

$323

Roundtrip

found 1 day ago

Select Delta flight, departing Thu, Sep 11 from Midway Intl. to Minneapolis - St. Paul Intl., returning Mon, Sep 15, priced at $323 found 1 day ago

Fri, Jun 6 - Mon, Jun 9

ORD

O'Hare Intl.

MSP

Minneapolis - St. Paul Intl.

$348 Roundtrip, found 1 day ago

$348

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Fri, Jun 6 from O'Hare Intl. to Minneapolis - St. Paul Intl., returning Mon, Jun 9, priced at $348 found 1 day ago

Thu, Sep 11 - Mon, Sep 15

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$363 Roundtrip, found 1 day ago

$363

Roundtrip

found 1 day ago

Select Delta flight, departing Thu, Sep 11 from Midway Intl. to Minneapolis - St. Paul Intl., returning Mon, Sep 15, priced at $363 found 1 day ago

Thu, Sep 11 - Mon, Sep 15

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$366 Roundtrip, found 1 day ago

$366

Roundtrip

found 1 day ago

Select Delta flight, departing Thu, Sep 11 from Midway Intl. to Minneapolis - St. Paul Intl., returning Mon, Sep 15, priced at $366 found 1 day ago

Thu, Sep 11 - Mon, Sep 15

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$375 Roundtrip, found 1 day ago

$375

Roundtrip

found 1 day ago

Select Delta flight, departing Thu, Sep 11 from Midway Intl. to Minneapolis - St. Paul Intl., returning Mon, Sep 15, priced at $375 found 1 day ago

Sat, Jun 7 - Wed, Jun 11

ORD

O'Hare Intl.

MSP

Minneapolis - St. Paul Intl.

$415 Roundtrip, found 3 days ago

$415

Roundtrip

found 3 days ago

Select Delta flight, departing Sat, Jun 7 from O'Hare Intl. to Minneapolis - St. Paul Intl., returning Wed, Jun 11, priced at $415 found 3 days ago

Thu, Sep 11 - Mon, Sep 15

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$418 Roundtrip, found 1 day ago

$418

Roundtrip

found 1 day ago

Select Delta flight, departing Thu, Sep 11 from Midway Intl. to Minneapolis - St. Paul Intl., returning Mon, Sep 15, priced at $418 found 1 day ago