$23 Cheap flight deals from Chicago (CHI) to Winter Garden (ORL)
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This Weekend's Flight Deals from Chicago to Winter Garden
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 $23 One Way, $46 Round Trip from Chicago to Winter Garden
Prices starting at $46 for return flights and $23 for one-way flights to Winter Garden 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 Garden economy flight packages
Westgate Town Center Resort
Mar 24 - Mar 28
Chicago (CHI) to Orlando (MCO)
Orlando (MCO) to Chicago (CHI)
Reviewed on Apr 6, 2025
Westgate Lakes Resort & Spa Universal Studios Area
Mar 24 - Mar 28
Chicago (CHI) to Orlando (MCO)
Orlando (MCO) to Chicago (CHI)
Reviewed on Feb 12, 2026
Winter Garden packages with premium economy flights
Westgate Town Center Resort
Mar 16 - Mar 19
Chicago (CHI) to Orlando (MCO)
Reviewed on Apr 6, 2025
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
Mar 16 - Mar 19
Chicago (CHI) to Orlando (MCO)
Reviewed on Jan 3, 2026
Westgate Lakes Resort & Spa Universal Studios Area
Mar 16 - Mar 19
Chicago (CHI) to Orlando (MCO)
Reviewed on Feb 12, 2026
More About Flying To Winter Garden from Chicago
Route Information for Flights from Chicago to Winter Garden
Origin Airport IATA Code | CHI |
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Destination Airport IATA Code | ORL |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Winter Garden
Whether you want to book cheap flights from Chicago to Winter Garden or are looking for the perfect package holiday, Orbitz is your one-stop source. Taking the stress and expense out of travel, Orbitz helps you find the best fares for Chicago to Winter Garden flights.
Make the Most of Your Vacation
Not only does Orbitz have cheap deals for Chicago to Winter Garden flights, we can also help you plan your vacation in advance. Why wait in lengthy lines for tickets to shows, amusement parks, and other attractions when you could be making the most of your holiday? Add activities to your flight booking for fewer hassles once you arrive in Winter Garden.
Planning on the Go
Book your flights from Chicago to Winter Garden wherever you are with the Orbitz app for Android and iPhone. Or simply use m.orbitz.com on your mobile browser to search and book the Chicago to Winter Garden flights that you want. And if you’re running late, you check your flight status and baggage claim information on your mobile device too too.
Craft Your Perfect Vacation
Orbitz takes the stress out of vacation planning with great deals on flights from Chicago to Winter Garden, hotels, car rentals, cruises, and more. Mix and match results for your perfect trip, or book a complete vacation package.
Keep Informed With Orbitz
With Orbitz’s free alerts service, you will stay informed of flight or services disruptions to your Chicago to Winter Garden flights. The alerts can be sent straight to your mobile phone or email.
Flights from Chicago
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Winter Garden Airports
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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.