Route guide
Cheap Flights from New York to Chicago: Book Airline Tickets
- Distance
- about 740 mi
- Typical flight time
- 1 h 45 min – 2 h 45 min
- Airports
- 3 × 2
- Time difference
- 1 h behind
This page covers the practical side of flying between New York and Chicago: which airports to compare, how long the trip takes, and when it is busy. It works for either direction. For a price on your dates, ask a specialist.
Airport pairs to compare
New York is served by three major airports across two states, so choosing the right airport is one of the biggest levers on both price and door-to-door time. Chicago has two main airports: O'Hare handles hub and long-haul traffic, while Midway is smaller and closer to the city center.
| Pair | Departure airport | Arrival airport |
|---|---|---|
| JFK to ORD | John F. Kennedy International | O'Hare International |
| JFK to MDW | John F. Kennedy International | Midway International |
| LGA to ORD | LaGuardia | O'Hare International |
| LGA to MDW | LaGuardia | Midway International |
| EWR to ORD | Newark Liberty International | O'Hare International |
| EWR to MDW | Newark Liberty International | Midway International |
Airlines with a major base at either end
- At New York: United Airlines, Delta Air Lines, American Airlines, JetBlue Airways
- At Chicago: United Airlines, American Airlines, Southwest Airlines
United Airlines, American Airlines have a base at both ends, which can make nonstop service more likely. Schedules change, so a specialist confirms what actually operates on your dates.
When to go and what to expect
New York
Spring (April to June) and fall (September to early November) bring the mildest weather. December fills up with holiday visitors, and late summer can be hot and humid.
Chicago
Late spring through early fall is the most pleasant stretch. Winter brings snow and cold that can cause delays.
Getting between the airport and town
New York: Subway, commuter rail and buses link all three airports to Manhattan. Taxis and ride-hail are everywhere but depend heavily on traffic.
Chicago: CTA trains run from both airports to the city center, which is usually the most predictable option at busy times.
Planning ground transport too? See our car rental guide.
Good to know
- Winter storms and summer thunderstorms are the usual causes of delays, so leave extra connection time in those seasons.
- Winter weather is the main source of disruption. Build in extra buffer for connections between November and March.
- Compare the total with bags included, not just the base fare. See baggage fees and taxes and fees.
Frequently asked questions
How far is New York from Chicago?
The straight-line distance between the main airports is about 740 miles (1,190 km). Routes can be longer in practice because of air traffic and weather.
How long is a flight from New York to Chicago?
A typical scheduled flight takes roughly 1 h 45 min to 2 h 45 min in the air, depending on winds, the aircraft and the airports. Connecting itineraries take longer, and nonstop availability depends on the airline and dates.
Which airports can I use?
At New York: JFK (John F. Kennedy International), LGA (LaGuardia), EWR (Newark Liberty International). At Chicago: ORD (O'Hare International), MDW (Midway International). Ask for prices on more than one pairing.
Is there a time difference?
Chicago is 1 hour behind New York.
Do you show fares on this page?
No. Fares change constantly, so we do not publish prices that might be out of date. A specialist checks live availability and confirms the full total, including taxes and bags, before you pay.