Cheap Flights from New York to Chicago — $73

The route New York — Chicago is served by many carriers — 5 in total, including JetBlue Airways, Southwest Airlines, American Airlines, United Airlines, and Frontier Airlines. This gives passengers wide opportunities: from finding the lowest fare (from $73) 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.

John F. Kennedy International (JFK) is New York’s primary international gateway and a major transatlantic and transpacific hub, typically serving full-service carriers alongside many international and premium airlines. It’s about 15–20 miles from Midtown Manhattan; travelers usually allow 45–75 minutes by car depending on traffic. Public options include the AirTrain connecting to the Long Island Rail Road or NYC Subway (travel times to Manhattan commonly range 50–70 minutes; fares vary by operator), plus taxis and app rides that can be pricier. Pros: extensive long-haul connectivity and full-service amenities. Cons: can be crowded and subject to variable traffic and longer transfer times. LaGuardia Airport (LGA) generally functions as New York’s domestic and short-haul regional airport, often favored by budget-conscious travelers and carriers focusing on U.S. routes. Located roughly 8–10 miles from Midtown, ground travel is usually 20–40 minutes by car when traffic is moderate. Transit options include buses and a short AirTrain-to-subway connection via the nearby transit network; fares are typically low but travel can be slower than driving. Pros: closer to Manhattan and convenient for short domestic hops. Cons: fewer international flights, more limited lounges, and potential congestion during peak hours. Newark Liberty International (EWR) is an important international and domestic hub in the New York metro, commonly used by both legacy carriers and many international airlines. Situated in New Jersey about 16–20 miles from Midtown Manhattan, journey times by car are frequently 30–60 minutes depending on traffic and bridge/tunnel conditions. The AirTrain links to NJ Transit and Amtrak at Newark Liberty International Airport Station, with typical total travel times to Penn Station around 30–50 minutes and fares varying by service. Pros: strong transcontinental and international connections and extensive airline options. Cons: less convenient to some Manhattan destinations and can involve tolls and variable commute times.

O'Hare International Airport (ORD) is Chicago's primary international hub, serving major global carriers and United's large operations alongside many international and legacy airlines. Flights can be competitive on price but often reflect hub status for premium routings. Located about 17 miles northwest of downtown, typical transfers to the Loop take 30–60 minutes depending on traffic; the CTA Blue Line rail runs to downtown in roughly 45 minutes with fares around $2.50–$3, while taxis or rideshares commonly cost in the $30–$60 range. Pros: extensive international connectivity and frequent flights; Cons: it can be busy and may require longer transit times between terminals.

In different months, ticket prices from New York to Chicago vary: minimum — $73 (October 2026), maximum — $204 (June 2027). Typically, the flight costs $116–$228.