Cheap Flights from Chicago to New York — $100

The route Chicago — New York is served by many carriers — 5 in total, including Southwest Airlines, United Airlines, American Airlines, JetBlue Airways, and Frontier Airlines. This gives passengers wide opportunities: from finding the lowest fare (from $100) 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.

All 4 airlines on the Chicago — New York route operate on a daily basis: United Airlines, American Airlines, JetBlue Airways, and Southwest Airlines fly every day.

Chicago is served by two main airports: O’Hare International (ORD) and Midway (MDW). O’Hare is the city’s primary international hub and usually handles the bulk of long-haul and premium carrier flights, as well as many domestic connections; fares here can be mid-to-high depending on season and carrier. It sits about 17 miles northwest of downtown; travelers can reach the Loop by CTA Blue Line in roughly 45–60 minutes or by taxi/ride-share in 30–60 minutes depending on traffic, with transit fares low and road transfers typically costing more. Pros: extensive route network and amenities; cons: busy terminals and occasional long transfers. Midway is typically oriented toward domestic and low-cost carriers and can offer more budget-friendly options on many routes. Located roughly 10 miles southwest of downtown, Midway connects via the CTA Orange Line in about 25–35 minutes, taxi/ride-share in 20–40 minutes, and often has simpler, quicker passenger flows. Pros: compact layout and easier transfers; cons: fewer international services and limited late-night options.

John F. Kennedy International (JFK) is New York’s primary international gateway and a major hub for full-service carriers, handling long-haul and transatlantic flights as well as many premium airline alliances. It’s located about 15 miles (24 km) southeast of Midtown Manhattan; typical options to the city include the AirTrain-plus-subway (around 50–70 minutes, moderate fare), express buses and taxis or rideshares (35–60 minutes depending on traffic, fares vary), and private shuttles. Travelers often find a wide range of amenities and lounge access, though peak-time congestion and longer transfer times can be downsides. Prices for flights can be mid-to-high depending on season and carrier.

In different months, ticket prices from Chicago to New York vary: minimum — $111 (September 2026), maximum — $740 (August 2026). Typically, the flight costs $135–$201.