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.

Sat, Jun 7 - Fri, Jun 13

ORD

O'Hare Intl.

MSP

Minneapolis - St. Paul Intl.

$195 Roundtrip, found 2 days ago

$195

Roundtrip

found 2 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 2 days ago

Thu, Sep 11 - Mon, Sep 15

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$200 Roundtrip, just found

$200

Roundtrip

just found

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

Thu, Jun 5 - Sat, Jun 7

ORD

O'Hare Intl.

MSP

Minneapolis - St. Paul Intl.

$204 Roundtrip, found 2 days ago

$204

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Thu, Jun 5 from O'Hare Intl. to Minneapolis - St. Paul Intl., returning Sat, Jun 7, priced at $204 found 2 days ago

Thu, Jun 5 - Fri, Jun 13

ORD

O'Hare Intl.

MSP

Minneapolis - St. Paul Intl.

$213 Roundtrip, found 2 days ago

$213

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Thu, Jun 5 from O'Hare Intl. to Minneapolis - St. Paul Intl., returning Fri, Jun 13, priced at $213 found 2 days ago

Thu, Sep 11 - Mon, Sep 15

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$226 Roundtrip, just found

$226

Roundtrip

just found

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

Thu, Jun 5 - Sun, Jun 8

ORD

O'Hare Intl.

MSP

Minneapolis - St. Paul Intl.

$240 Roundtrip, found 2 days ago

$240

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Thu, Jun 5 from O'Hare Intl. to Minneapolis - St. Paul Intl., returning Sun, Jun 8, priced at $240 found 2 days ago

Thu, Sep 11 - Mon, Sep 15

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$256 Roundtrip, just found

$256

Roundtrip

just found

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

Thu, Sep 11 - Mon, Sep 15

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$317 Roundtrip, just found

$317

Roundtrip

just found

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

Thu, Sep 11 - Mon, Sep 15

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$323 Roundtrip, just found

$323

Roundtrip

just found

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

Thu, Sep 11 - Mon, Sep 15

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$363 Roundtrip, just found

$363

Roundtrip

just found

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

Thu, Sep 11 - Mon, Sep 15

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$366 Roundtrip, just found

$366

Roundtrip

just found

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

Thu, Sep 11 - Mon, Sep 15

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$375 Roundtrip, just found

$375

Roundtrip

just found

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

Sat, Jun 7 - Wed, Jun 11

ORD

O'Hare Intl.

MSP

Minneapolis - St. Paul Intl.

$415 Roundtrip, found 2 days ago

$415

Roundtrip

found 2 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 2 days ago

Thu, Sep 11 - Mon, Sep 15

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$418 Roundtrip, just found

$418

Roundtrip

just found

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

Thu, Sep 11 - Mon, Sep 15

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$425 Roundtrip, just found

$425

Roundtrip

just found

Select Delta flight, departing Thu, Sep 11 from Midway Intl. to Minneapolis - St. Paul Intl., returning Mon, Sep 15, priced at $425 just found

Thu, Sep 11 - Mon, Sep 15

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$433 Roundtrip, just found

$433

Roundtrip

just found

Select Delta flight, departing Thu, Sep 11 from Midway Intl. to Minneapolis - St. Paul Intl., returning Mon, Sep 15, priced at $433 just found

Thu, Sep 11 - Mon, Sep 15

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$436 Roundtrip, just found

$436

Roundtrip

just found

Select Delta flight, departing Thu, Sep 11 from Midway Intl. to Minneapolis - St. Paul Intl., returning Mon, Sep 15, priced at $436 just found

Wed, Jun 4 - Tue, Jun 10

ORD

O'Hare Intl.

MSP

Minneapolis - St. Paul Intl.

$483 Roundtrip, found 2 days ago

$483

Roundtrip

found 2 days ago

Select Delta flight, departing Wed, Jun 4 from O'Hare Intl. to Minneapolis - St. Paul Intl., returning Tue, Jun 10, priced at $483 found 2 days ago

Wed, Jun 4 - Tue, Jun 10

ORD

O'Hare Intl.

MSP

Minneapolis - St. Paul Intl.

$486 Roundtrip, found 2 days ago

$486

Roundtrip

found 2 days ago

Select American Airlines flight, departing Wed, Jun 4 from O'Hare Intl. to Minneapolis - St. Paul Intl., returning Tue, Jun 10, priced at $486 found 2 days ago

Wed, Jun 4 - Tue, Jun 10

ORD

O'Hare Intl.

MSP

Minneapolis - St. Paul Intl.

$503 Roundtrip, found 2 days ago

$503

Roundtrip

found 2 days ago

Select United flight, departing Wed, Jun 4 from O'Hare Intl. to Minneapolis - St. Paul Intl., returning Tue, Jun 10, priced at $503 found 2 days ago