Cheap Flights from Chicago to Orlando — $58

The Chicago — Orlando route is served by a wide range of airlines: 6 in total, including Frontier Airlines, Allegiant Air, United Airlines, Sun Country Airlines, Southwest Airlines, and Air Canada. Competition among carriers gives passengers the opportunity to find tickets at attractive fares — with prices starting from $58. Our service helps compare all available offers within seconds and choose the most convenient option. You can filter flights by price, departure time, or baggage rules to make your trip as comfortable as possible. With so many airlines, there’s always a chance to catch special promotions and save.

The distance between Chicago and Orlando is 1587km (984 miles). There are 122 direct flights from Chicago to Orlando. The time difference between Chicago and Orlando is 1h. Flights from Chicago begin at 5:10 AM. The latest flight from Chicago departs at 8:35 PM

Chicago is served by two major airports with distinct roles. O’Hare International (ORD) is the city’s primary international and connecting hub, typically handling many legacy carriers and long-haul flights; it can be pricier on some routes but often offers the most nonstop options. Midway (MDW) functions more as a domestic and low-cost carrier base, usually attracting budget-conscious travelers and regional services. O’Hare is about 17–20 miles northwest of downtown (roughly 30–60 minutes by car depending on traffic); options include the CTA Blue Line train (~45–60 minutes, budget-friendly) and shuttle/taxi/Ridehail services that can cost more. Midway sits around 10 miles southwest of downtown (about 20–40 minutes by car) and is connected by the CTA Orange Line (~25–35 minutes, low fare), plus buses and taxis. O’Hare offers more airline choice and long-haul amenities but can be busier and involve longer transfers; Midway is often quicker and more convenient for domestic travelers, though it has fewer international connections.

The minimum one-way ticket price from Chicago to Orlando is $51 (September 2026), while the maximum is $85 (June 2026). On average, a ticket costs $68–$75.

Orlando’s air traffic is split between Orlando International (MCO), the main international hub handling most long-haul and major-carrier flights, and smaller airports like Orlando Sanford (SFB), which typically serves budget and charter services. MCO sits about 13 miles southeast of downtown Orlando, with airport shuttles, ride-hailing and taxi trips usually taking 20–30 minutes depending on traffic; SunRail plus local buses are options for cheaper connections. Sanford is around 30 miles north and can be 40–60 minutes away by road, often preferred for low-cost carriers and seasonal charters. Expect MCO to feel busier and more amenity-rich, while Sanford can be simpler and sometimes cheaper — trade-offs are comfort and frequency versus lower fares and less congestion.