Cheap Flights from Orlando to Chicago Starting at $37

The route Orlando — Chicago is served by many carriers — 8 in total, including Spirit Airlines, American Airlines, Southwest Airlines, United Airlines, Frontier Airlines, Allegiant Air, JetBlue Airways, and Air Canada. This gives passengers wide opportunities: from finding the lowest fare (from $37) to selecting flights by schedule or service class. Our service aggregates data from multiple booking systems so you can compare offers in one place. This saves time and money: no need to check dozens of sites — just pick the right option and book online.

Orlando International Airport (MCO) is the region’s primary international gateway and a major hub for both legacy and low-cost carriers, so fares can range from budget-friendly to premium depending on season. It sits about 13 miles (20 km) southeast of downtown Orlando, with shuttle services, ride-shares and taxis typically taking 20–30 minutes and costing roughly $30–$60; the SunRail plus shuttle options can be cheaper but add transfer time. Orlando Sanford (SFB) serves more low-cost and leisure-focused airlines and is farther north, around 30–40 minutes from central Orlando by car. MCO offers more nonstop choices and amenities; SFB can be quieter and less expensive but has fewer transport links and longer transfers to the city.

Chicago is served mainly by O'Hare International (ORD) and Midway (MDW), with ORD typically functioning as the city’s large international and domestic hub—favored by major network carriers—while MDW generally handles more domestic and budget-oriented flights. O’Hare sits about 17–20 miles northwest of downtown; travel by CTA Blue Line usually takes 45–60 minutes and can be cheaper than airport shuttles or taxis, which commonly run 30–60 minutes depending on traffic. Midway is roughly 10 miles southwest and is often quicker to reach from the Loop, with the CTA Orange Line taking about 25–35 minutes and lower fares than private rides. O’Hare offers extensive international connections and plentiful amenities but can be busy and spread out; Midway can be more compact and easier to navigate for domestic trips but has fewer nonstop long-haul options. Both airports provide ride-hailing, shuttle, and car-rental services, with regional commuter and bus links for budget-conscious travelers.