Cheap Flights from Chicago to Philadelphia — $102

The Chicago — Philadelphia route is served by a wide range of airlines: 4 in total, including Southwest Airlines, United Airlines, American Airlines, and Frontier Airlines. Competition among carriers gives passengers the opportunity to find tickets at attractive fares — with prices starting from $102. 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.

Chicago is served by two main commercial airports with distinct roles. O’Hare International (ORD) is a major international and connecting hub, typically hosting legacy carriers like United and American alongside a wide range of global airlines; it can be pricier for last-minute or premium flights but often offers more international and nonstop options. O’Hare sits about 17–20 miles northwest of downtown; typical transport choices include the CTA Blue Line train (roughly 45–60 minutes, low fare), airport shuttle or rideshare (35–60 minutes, fares vary), and taxis. Pros: extensive flight choice and facilities; cons: large layout and potential congestion. Midway (MDW) functions more as a domestic/budget-oriented airport, commonly used by low-cost carriers such as Southwest and some regional airlines. Midway is around 10 miles southwest of the Loop; travel options include CTA Orange Line (25–35 minutes, inexpensive), shuttle or rideshare (20–40 minutes, cost dependent), and taxis. Pros: generally quicker ground access and simpler layouts; cons: fewer international routes and smaller amenity selection compared with O’Hare.

Philadelphia International Airport (PHL) is the region’s primary international gateway and a major hub for transatlantic and domestic connections, typically serving legacy carriers and a mix of low-cost airlines. Located about 7 miles southwest of downtown Philly, travel into the city center usually takes 20–30 minutes by car depending on traffic, with taxis and rideshares commonly ranging from moderate to higher fares; regional rail (SEPTA) connects on a short shuttle with roughly 25–35 minute journeys at budget-friendly fares. Parking and terminal distances can add time, so factor in transfer and security waits. Pros: wide route choice and full-service amenities; cons: can be busy during peak hours and ground transportation may be affected by traffic.