Cheap Flights from Philadelphia to Chicago — $98

The route Philadelphia — Chicago is served by many carriers — 5 in total, including United Airlines, Southwest Airlines, American Airlines, Frontier Airlines, and JetBlue Airways. This gives passengers wide opportunities: from finding the lowest fare (from $98) 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.

Philadelphia International Airport (PHL) serves as the region’s primary international and domestic gateway, typically handling a mix of major network carriers and several low-cost airlines. It’s often regarded as a full-service hub for connecting flights rather than a budget-only option. PHL sits about 7–10 miles southwest of downtown Philadelphia; travel by SEPTA regional rail usually takes 25–30 minutes and can be a cost-effective choice, while taxis or app rides typically take 20–35 minutes depending on traffic and can be pricier. Ground transport also includes shuttle and rental-car services. Pros: frequent nonstop options and convenient rail links. Cons: can be busy during peak hours and terminal walking distances may be long.

O’Hare International (ORD) is Chicago’s primary international hub and a major connection point for both full-service and many low-cost carriers, so fares can vary widely but often include competitive options. Located roughly 17 miles northwest of downtown, it’s usually reached by CTA Blue Line trains in about 40–50 minutes (fare around the standard transit price) or by taxi/ride-share in 30–60 minutes depending on traffic, with higher costs during peak times. Pros: extensive global connections, comprehensive passenger facilities. Cons: can be busy and spread out, which may mean longer transfer or wait times during peak periods. Midway Airport (MDW) functions more as a convenient domestic and regional airport popular with budget and leisure carriers; it can be a good option for shorter U.S. flights and often shows lower base fares for point-to-point travel. Sitting about 10 miles southwest of the Loop, Midway is typically reachable by CTA Orange Line in roughly 25–30 minutes (transit fare applies) or by car in 20–45 minutes depending on traffic, with generally lower ground-transport costs versus O’Hare. Pros: compact layout and quicker terminal transfers. Cons: fewer international routes and smaller on-site amenities compared with the larger hub.

In different months, ticket prices from Philadelphia to Chicago vary: minimum — $99 (September 2026), maximum — $114 (August 2026). Typically, the flight costs $106–$114.