$34 Cheap flight deals from Chicago (CHI) to Kissimmee (ORL)
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This Weekend's Flight Deals from Chicago to Kissimmee
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 $34 One Way, $68 Round Trip from Chicago to Kissimmee
Prices starting at $68 for return flights and $34 for one-way flights to Kissimmee were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Kissimmee economy flight packages
Palazzo Lakeside Hotel
Dec 10 - Dec 16
Chicago (CHI) to Orlando (MCO)
Orlando (MCO) to Chicago (CHI)
Reviewed on Jul 19, 2025
Summerville Vacation Homes by Columbia Management
Dec 26 - Dec 31
Chicago (CHI) to Orlando (MCO)
Orlando (MCO) to Chicago (CHI)
Reviewed on Apr 19, 2021
Westgate Palace Hotel / Universal / I-Drive
Dec 26 - Dec 31
Chicago (CHI) to Orlando (MCO)
Orlando (MCO) to Chicago (CHI)
Reviewed on Aug 6, 2025
More About Flying To Kissimmee from Chicago
Route Information for Flights from Chicago to Kissimmee
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | ORL |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Kissimmee
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Kissimmee 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.