$48 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.
Airfares from $48 One Way, $118 Round Trip from Chicago to Winter Park
Prices starting at $118 for return flights and $48 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.
Winter Park economy flight packages
Disney's Animal Kingdom Lodge
Nov 26 - Nov 30
Chicago (CHI) to Orlando (MCO)
Reviewed on Oct 9, 2026
Winter Park business class flight packages
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
Nov 12 - Nov 16
Chicago (ORD) to Orlando (MCO)
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.