$29 Cheap flight deals from Chicago (CHI) to Kissimmee (ORL)
Earn rewards on top of your airline miles with Orbitz Rewards
Many airlines offer flexible change policies
Sign up to receive text alerts about your trip
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 $29 One Way, $100 Round Trip from Chicago to Kissimmee
Prices starting at $100 for return flights and $29 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
Westgate Town Center Resort
Jun 12 - Jun 16
Chicago (CHI) to Orlando (MCO)
Orlando (MCO) to Chicago (CHI)
Reviewed on Apr 15, 2026
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
Jun 22 - Jun 29
Chicago (CHI) to Orlando (MCO)
Reviewed on Jan 3, 2026
Florida Hotel & Conference Center in the Florida Mall
Jun 27 - Jul 5
Chicago (MDW) to Orlando (MCO)
Orlando (MCO) to Chicago (MDW)
Reviewed on Dec 9, 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
Whether you want to book cheap flights from Chicago to Kissimmee 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 Kissimmee flights.
Make the Most of Your Vacation
Not only does Orbitz have cheap deals for Chicago to Kissimmee 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 Kissimmee.
Planning on the Go
Book your flights from Chicago to Kissimmee 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 Kissimmee 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 Kissimmee, 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 Kissimmee flights. The alerts can be sent straight to your mobile phone or email.
Flights from Chicago
- Chicago to Orlando
- Chicago to Houston
- Chicago to New York
- Chicago to Phoenix
- Chicago to Dallas
- Chicago to Los Angeles
- Chicago to New Orleans
- Chicago to London
- Chicago to Washington
- Chicago to Paris
- Chicago to Toronto
- Chicago to Rome
- Chicago to San Francisco
- Chicago to Cleveland
- Chicago to Detroit
- Chicago to Montreal
- Chicago to Sacramento
- Chicago to Kansas City
- Chicago to Hartford
- Chicago to Atlantic City
Kissimmee Airports
More Destinations
- Flights from Allentown (ABE) to Orlando (MCO)
- Flights from Atlanta (ATL) to Orlando (MCO)
- Flights from Wilkes-Barre (AVP) to Orlando (MCO)
- Flights from Hartford (BDL) to Orlando (MCO)
- Flights from Bloomington (BMI) to Orlando (MCO)
- Flights from Nashville (BNA) to Orlando (MCO)
- Flights from Burlington (BTV) to Orlando (MCO)
- Flights from Buffalo (BUF) to Orlando (MCO)
- Flights from Baltimore (BWI) to Orlando (MCO)
- Flights from Akron (CAK) to Orlando (MCO)
- Flights from Chattanooga (CHA) to Orlando (MCO)
- Flights from Cleveland (CLE) to Orlando (MCO)
- Flights from Charlotte (CLT) to Orlando (MCO)
- Flights from Columbus (CMH) to Orlando (MCO)
- Flights from Cincinnati (CVG) to Orlando (MCO)
- Flights from Washington (DCA) to Orlando (MCO)
- Flights from Denver (DEN) to Orlando (MCO)
- Flights from Dallas (DFW) to Orlando (MCO)
- Flights from Des Moines (DSM) to Orlando (MCO)
- Flights from Detroit (DTW) to Orlando (MCO)
- Flights from Dubai (DXB) to Orlando (MCO)
- Flights from Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
- Flights from Fort Lauderdale (FLL) to Orlando (MCO)
- Flights from Flint (FNT) to Orlando (MCO)
- Flights from Grand Rapids (GRR) to Orlando (MCO)
- Flights from Greenville (GSP) to Orlando (MCO)
- Flights from Houston (HOU) to Orlando (MCO)
- Flights from White Plains (HPN) to Orlando (MCO)
- Flights from Huntsville (HSV) to Orlando (MCO)
- Flights from Washington (IAD) to Orlando (MCO)
- Flights from Houston (IAH) to Orlando (MCO)
- Flights from Wichita (ICT) to Orlando (MCO)
- Flights from Indianapolis (IND) to Orlando (MCO)
- Flights from Islip (ISP) to Orlando (MCO)
- Flights from New York (JFK) to Orlando (MCO)
- Flights from Los Angeles (LAX) to Orlando (MCO)
- Flights from Latrobe (LBE) to Orlando (MCO)
- Flights from New York (LGA) to Orlando (MCO)
- Flights from Kansas City (MCI) to Orlando (MCO)
- Flights from Harrisburg (MDT) to Orlando (MCO)
- Flights from Memphis (MEM) to Orlando (MCO)
- Flights from Manchester (MHT) to Orlando (MCO)
- Flights from Miami (MIA) to Orlando (MCO)
- Flights from Milwaukee (MKE) to Orlando (MCO)
- Flights from Madison (MSN) to Orlando (MCO)
- Flights from New Orleans (MSY) to Orlando (MCO)
- Flights from Oklahoma City (OKC) to Orlando (MCO)
- Flights from Ontario (ONT) to Orlando (MCO)
- Flights from Chicago (ORD) to Orlando (MCO)
- Flights from Norfolk (ORF) to Orlando (MCO)
- Flights from Portland (PDX) to Orlando (MCO)
- Flights from Philadelphia (PHL) to Orlando (MCO)
- Flights from Pittsburgh (PIT) to Orlando (MCO)
- Flights from Portsmouth (PSM) to Orlando (MCO)
- Flights from Providence (PVD) to Orlando (MCO)
- Flights from Portland (PWM) to Orlando (MCO)
- Flights from Raleigh (RDU) to Orlando (MCO)
- Flights from Rockford (RFD) to Orlando (MCO)
- Flights from Richmond (RIC) to Orlando (MCO)
- Flights from Rochester (ROC) to Orlando (MCO)
- Flights from Fort Myers (RSW) to Orlando (MCO)
- Flights from San Diego (SAN) to Orlando (MCO)
- Flights from San Antonio (SAT) to Orlando (MCO)
- Flights from Santo Domingo (SDQ) to Orlando (MCO)
- Flights from Seattle (SEA) to Orlando (MCO)
- Flights from San Francisco (SFO) to Orlando (MCO)
- Flights from Weyers Cave (SHD) to Orlando (MCO)
- Flights from San Juan (SJU) to Orlando (MCO)
- Flights from Salt Lake City (SLC) to Orlando (MCO)
- Flights from Sacramento (SMF) to Orlando (MCO)
- Flights from Orange County (SNA) to Orlando (MCO)
- Flights from Santiago (STI) to Orlando (MCO)
- Flights from Newburgh (SWF) to Orlando (MCO)
- Flights from Syracuse (SYR) to Orlando (MCO)
- Flights from Tampa (TPA) to Orlando (MCO)
- Flights from Trenton (TTN) to Orlando (MCO)
- Flights from Knoxville (TYS) to Orlando (MCO)
- Flights from Fort Walton Beach (VPS) to Orlando (MCO)
- Flights from Atlanta to Orlando
- Flights from Boston to Orlando
- Flights from Charlotte to Orlando
- Flights from Chicago to Orlando
- Flights from Cleveland to Orlando
- Flights from Columbus to Orlando
- Flights from Dallas to Orlando
- Flights from Denver to Orlando
- Flights from Detroit to Orlando
- Flights from Houston to Orlando
- Flights from Memphis to Orlando
- Flights from Miami to Orlando
- Flights from Nashville to Orlando
- Flights from New York to Orlando
- Flights from Philadelphia to Orlando
- Flights from Toronto to Orlando
- Flights from Washington to Orlando
- Flights from Providence to Orlando
- Flights from Pittsburgh to Orlando
- Flights from Newark to Orlando
- Flights from Richmond to Orlando
- Flights from Buffalo to Orlando
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.