$30 Cheap flight deals from Chicago (CHI) to Winter Park (ORL)

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This Weekend's Flight Deals from Chicago to Winter Park

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Jan 11 - Sun, Jan 18
MDW
Midway Intl.
MCO
Orlando Intl.
$140 Roundtrip, found 8 hours ago
$140
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sun, Jan 11 from Midway Intl. to Orlando Intl., returning Sun, Jan 18, priced at $140 found 8 hours ago
Sat, Jan 10 - Sat, Jan 17
ORD
O'Hare Intl.
MCO
Orlando Intl.
$162 Roundtrip, found 2 hours ago
$162
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Jan 10 from O'Hare Intl. to Orlando Intl., returning Sat, Jan 17, priced at $162 found 2 hours ago
Fri, Jan 9 - Sun, Jan 18
RFD
Greater Rockford
MCO
Orlando Intl.
$331 Roundtrip, found 2 days ago
$331
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Jan 9 from Greater Rockford to Orlando Intl., returning Sun, Jan 18, priced at $331 found 2 days ago

Airfares from $30 One Way, $58 Round Trip from Chicago to Winter Park

Prices starting at $58 for return flights and $30 for one-way flights to Winter Park were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Feb 8 - Sat, Feb 21
MDW
Chicago
MCO
Orlando
$58 Roundtrip, found 1 day ago
$58
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Feb 8 from Chicago to Orlando, returning Sat, Feb 21, priced at $58 found 1 day ago
Sun, Jan 18 - Thu, Jan 29
ORD
Chicago
MCO
Orlando
$58 Roundtrip, found 5 hours ago
$58
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sun, Jan 18 from Chicago to Orlando, returning Thu, Jan 29, priced at $58 found 5 hours ago
Wed, Feb 4 - Thu, Feb 12
ORD
Chicago
MCO
Orlando
$79 Roundtrip, found 2 hours ago
$79
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Wed, Feb 4 from Chicago to Orlando, returning Thu, Feb 12, priced at $79 found 2 hours ago
Tue, Feb 3 - Tue, Feb 10
ORD
Chicago
MCO
Orlando
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Feb 3 from Chicago to Orlando, returning Tue, Feb 10, priced at $157 found 1 day ago
Sat, Feb 14 - Tue, Feb 17
ORD
Chicago
MCO
Orlando
$157 Roundtrip, found 5 hours ago
$157
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Sat, Feb 14 from Chicago to Orlando, returning Tue, Feb 17, priced at $157 found 5 hours ago

Winter Park economy flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort
4.0-star property

Westgate Town Center Resort

8/10 Very Good! (1,367 reviews)

Feb 6 - Feb 11

5 night stay

Chicago (CHI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Price was $602, price is now $249 per person
$249
per person
found 1 day ago
We took our 3 year old nephew here and he had a BLAST! There is so much to do, we didn’t leave for 2 of the 3 days that we stayed. He’s about 42 inches which got him on most of the slides but not all. Keep size in mind when booking for little ones because if they’re under 40in they’re limited to the slides. He was a little bummed that he couldn’t do the pirates plunge (biggest slide) but there were enough distractions that it didn’t matter. Also, the lazy river is great! Just be careful with the big kids, they tend to knock the little ones over or into the wall because they’re just running through it. The water park is an extra fee FYI There’s “ice” skating, swan paddle boats, water park, mini golf, a train trolly, restaurants, arcade, jungle gym, multiple pools. Definitely a good spot if you don’t want to do the parks every day that you’re there! Highly recommend.

Reviewed on Apr 6, 2025

The Shores Resort & Spa
4.0-star property

The Shores Resort & Spa

9/10 Wonderful! (1,681 reviews)

Feb 4 - Feb 11

7 night stay

Chicago (ORD) to Orlando (MCO)

Spirit Airlines • Coach

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • Coach
Price was $837, price is now $321 per person
$321
per person
found 1 day ago
Pretty hotel with nice layout and nice rooms. Great restaurant and friendly staff.

Reviewed on Sep 20, 2025

Boardwalk Inn and Suites
2.5-star property

Boardwalk Inn and Suites

8.4/10 Very Good! (1,533 reviews)

Feb 4 - Feb 11

7 night stay

Chicago (ORD) to Orlando (MCO)

Spirit Airlines • Coach

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • Coach
Price was $570, price is now $278 per person
$278
per person
found 1 day ago
Nice room, liked pool and spa. At this location unfortunately no breakfast and no breakfast restaurants nearby.

Reviewed on Dec 3, 2025

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More About Flying To Winter Park from Chicago

Route Information for Flights from Chicago to Winter Park

Origin Airport IATA Code
CHI
Destination Airport IATA Code
ORL
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Winter Park

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.