Cheap Flights from Phoenix to Chicago Starting at $35

The Phoenix — Chicago route is served by a wide range of airlines: 4 in total, including American Airlines, Allegiant Air, Southwest Airlines, and Frontier Airlines. Competition among carriers gives passengers the opportunity to find tickets at attractive fares — with prices starting from $35. 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.

Phoenix is primarily served by Phoenix Sky Harbor International (PHX), the region’s main international and domestic hub that handles a mix of legacy carriers and low-cost airlines; Sky Harbor typically offers the widest choice of nonstop routes and can be mid-range in price compared with smaller airports. The airport sits about 4 miles east of downtown Phoenix, reachable by light rail in roughly 20–25 minutes or by car/taxi in 15–20 minutes depending on traffic; ride-hailing and taxis usually range from moderate to higher fares, while the Valley Metro light rail is generally the most economical option. Pros: convenient location, many flight options and frequent service; cons: busy peak periods and occasional congestion between terminals.

Fly nonstop from Phoenix to Chicago for the quickest, most convenient way to bridge the Southwest and the Windy City — ideal if you value time and comfort. While connection routes can sometimes be cheaper, a direct flight gets you to downtown Chicago faster with fewer hassles, so consider booking direct for a smoother trip.

O'Hare International Airport (ORD) is Chicago's primary global hub, handling large volumes of international and domestic flights and serving as a major base for legacy carriers and several global alliances. It is located about 17 miles northwest of downtown; typical travel time is 30–60 minutes by car depending on traffic, with taxi and rideshare fares usually in a mid-to-high range. Public transit via the Blue Line offers a more economical option, taking roughly 45–60 minutes for a fixed, budget-friendly fare. Pros: extensive route options and on-site amenities; cons: busy terminals and potential for delays during peak periods. Midway International Airport (MDW) functions as Chicago's more compact, budget-leaning airport, often favored by low-cost and domestic carriers for shorter-haul routes. Midway sits about 10 miles southwest of the Loop, with travel times typically around 20–40 minutes by car and generally lower taxi/rideshare costs than the larger hub. The Orange Line provides a direct subway link to downtown in approximately 25–35 minutes for an economical fare. Pros: quicker check-in and simpler layout; cons: fewer long-haul services and more limited international connections compared with the larger hub.

We carefully collect statistics on the search and pricing of airlines and, based on these data, we make an assumption about future prices. Thus, you can better understand which season is the cheapest to fly from Phoenix to Chicago