
Orlando to Chicago Flight Tickets
Compare the best flight deals from Orlando to Chicago
About Orlando - Chicago Flights
Find the best prices for flights between Orlando (United States) and Chicago (United States) on Tripuck. We compare prices from hundreds of airlines to offer you the best options.
Orlando has 3 airports, while Chicago has 6 airports. Compare flights between all airports to find the best deal.
Cheapest Months for Orlando - Chicago Flights
Best month to fly
October 2026 - 2.612 ₺
October 2026
2.612 ₺
Direct
CheapestDecember 2026
2.966 ₺
1 stops
November 2026
5.003 ₺
Direct
January 2027
5.933 ₺
Direct
| Ay | Flight Type | Price |
|---|---|---|
| October 2026Cheapest | Direct | 2.612 ₺ |
| December 2026 | 1 stops | 2.966 ₺ |
| November 2026 | Direct | 5.003 ₺ |
| January 2027 | Direct | 5.933 ₺ |
Prices may change. Based on recent searches.
Popular Orlando - Chicago Flights
Orlando - Chicago



Chicago - Orlando


Airlines on Orlando - Chicago Route
| Havayolu | Uçuş Tipi | Fiyat |
|---|---|---|
| Direct | 2.612 ₺ | |
| 1 stops | 2.966 ₺ |
Orlando Airports
Chicago Airports
Alternative Routes
Alternative Routes from Orlando
Orlando - Chicago Flight Summary
Cheaper tickets are usually available on weekdays and with early bookings.
Orlando and Chicago - Airport Transportation
Orlando International Airport (MCO)
How to Get to the Airport
Bus (LYNX): You can return to MCO from downtown using the same lines from LYNX Central Station or downtown stops. The journey takes approximately 40-50 minutes. Services depart every 30-60 minutes and operate between 5:00 AM and 12:00 AM.
Shuttle (Shared Shuttle Services): You can return to MCO from downtown with reserved shuttles from hotel or downtown pickup points. The journey takes 30-45 minutes. Services are scheduled every 30 minutes based on reservations and operate 24 hours.
Taxi: You can call a taxi to MCO from downtown streets or hotels. The journey takes 20-30 minutes depending on traffic. It operates 24 hours and is always available.
Uber/Lyft (App-Based Rides): You can reach MCO from any point in downtown with Uber or Lyft vehicles. The journey takes 20-30 minutes depending on traffic. The apps operate 24 hours, and vehicles are available every 5-10 minutes.
Car Rental: You can reach MCO by picking up rental cars from downtown offices. You can return your vehicles to the rental offices at the airport. This option is suitable for those seeking a flexible travel plan.
Orlando Executive Airport (ORL)
How to Get to the Airport
Taxi:
To reach Orlando Executive Airport from the city center of Orlando, you can call a taxi from official taxi stands or from the street. The travel time varies between 10-20 minutes depending on traffic. Taxi service is provided 24 hours upon request.
Uber/Lyft (Rideshare):
You can use Uber and Lyft apps to go to the airport from the city center of Orlando. Depending on traffic congestion, the journey takes approximately 10-20 minutes. These services are also available 24 hours a day and can be requested instantly through the app.
Car Rental:
You can reach Orlando Executive Airport by renting a car from car rental offices located in the city center. The journey to the airport with a rental car takes 10-15 minutes depending on traffic conditions. Car rental companies generally operate from 8:00 AM to 8:00 PM; however, it is possible to pick up a car 24 hours a day with a reservation.
Chicago Midway International Airport (MDW)
From Airport to City Center
Metro/Train: The CTA Orange Line station is located at the end of the enclosed pedestrian walkway connected to the terminal building. The train reaches the Loop area from MDW in approximately 25 minutes. The frequency of service varies depending on the time of day: generally every 3–15 minutes on weekdays, approximately every 10–15 minutes on Saturdays, and about every 10–15 minutes on Sundays and holidays. Operating hours from MDW to the Loop are weekdays 03:30–01:05, Saturdays 04:00–01:05, and Sundays and holidays 04:30–01:05.
Bus: There is no direct, regular, and fast CTA bus line between MDW and the city center; therefore, the Orange Line is generally preferred for transportation to the city center. The N62 Archer bus, which serves the airport, is an alternative CTA line that operates throughout the night; however, its route does not go directly to the Loop and may require a transfer. The frequency and hours of the N62 line may vary according to the schedule.
Taxi: Taxi services are available at the airport. The taxi stand is conveniently located outside the terminal building. Travel time may vary depending on traffic conditions, but generally, it takes 20-30 minutes to reach the city center. Taxi services operate 24 hours a day.
Uber/Bolt: App-based ride-hailing services like Uber and Bolt are also available at the airport. Vehicles you request through the app will be waiting for you in designated areas outside the airport terminal. Travel time and cost may vary depending on traffic conditions.
Car Rental: There are many car rental companies at the airport. You can prepare the necessary documents for rental and head to the car rental offices located within the terminal to rent the vehicle you want. Car rental services are generally open 24 hours.
O'Hare International Airport (ORD)
From Airport to City Center
Metro/Train: The CTA Blue Line Train is the most convenient option for transportation from O'Hare International Airport to downtown Chicago. The airport station is directly connected to Terminals 1, 2, and 3. Access from Terminal 5 is possible via a free shuttle train. The journey takes approximately 40-45 minutes. Services operate 24 hours a day, with trains running every 5-10 minutes during peak hours.
Bus (CTA and Private Shuttles): Buses connecting O'Hare Terminals 1, 2, 3, and 5 operate routes to downtown. The journey time varies between 45-60 minutes depending on traffic conditions. Services run every 15-30 minutes and generally operate from 5:00 AM to 11:45 PM.
Taxi: Official taxi stands at O'Hare are located at each terminal exit and provide direct transportation to downtown. The journey time varies between 30-60 minutes depending on traffic. Taxi services are available 24 hours a day.
Airport App-Based Rides (Uber/Lyft): Apps like Uber and Lyft operate in designated pickup areas at O'Hare. Journey time and cost can vary based on traffic and demand.
Car Rental: Various car rental companies are available at the airport. Car rental options can be arranged at offices located at terminal exits or at rental centers accessible via shuttle services.

