C$ 189 Find Cheap Flights from New York to Chicago – Compare and Save

These are the earliest and latest flight times available from New York to Chicago:

• Earliest: departs at 5:02 am and lands at 7:54 am
• Latest: departs at 10:13 pm and lands at 1:05 am.

The flight takes about 2h 52m.

Only Economy Class is available on flights from New York to Chicago.

A direct flight from New York to Chicago takes 2h 52m, covering 1,841 km.

No, a passport is not required for this domestic route, but you will need another form of identification, such as a driver's licence.

Round-trip flights from New York to Chicago range from C$ 277 to C$ 515, with an average of C$ 388 over the past 12 months. Anything below C$ 277 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 25% above the C$ 388 route average. Book 6 weeks before departure for the lowest fares.

On this route, layover flights are cheaper than direct options on average. Layover fares average C$ 284 round-trip via Fort Lauderdale (FLL), compared to C$ 388 for direct.

United Airlines is slightly above the route average for timely arrivals, while American Airlines has a lower on-time arrival rate. On-time arrival rates on New York to Chicago flights are:

• United Airlines: 87% on time
• American Airlines: 85% on time
• Delta: 83% on time

On average, flights on this route are punctual 83% of the time.

There is no standard. Checked bag policies vary by airline on this route. Most carriers charge C$ 49–C$ 141 for the first checked bag in economy. Premium fares and elite status bookings typically include a free checked bag.

Morning is the busiest departure period on New York to Chicago flights, with 46% leaving in that window. Afternoon departures account for 29%, Evening flights for 22%, and Night flights for 3%.

Three airlines offer in-flight Wi-Fi on New York to Chicago flights:

• American Airlines
• Delta
• JetBlue

Pricing varies by airline and fare class. Some plans are included with the ticket or loyalty program; others are paid add-ons priced by flight length.

Based on prices from the last 5 days, flying between New York and Chicago is around C$ 387 round-trip, with a flight time of about 14h 12m. Taking the train is much cheaper at around C$ 325 round-trip, with a trip time of about 19h 32m. The bus is similarly priced at around C$ 230 round-trip and takes about 16h 55m. Compared to flying, recent train and bus fares are roughly 29% lower. However, those options take about 4+ hours longer each way.

One-way fares from New York to Chicago are currently lower than usual. Average one-way flight prices are about C$ 213, which is 20% below the typical average for this route.

Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Chicago O'Hare Intl Airport (ORD) – daily rates averaging C$ 89:

• Routes Car & Truck Rentals
• Europcar
• Hertz
• Ace
• Dollar

Near Chicago Midway Airport (MDW) – daily rates averaging C$ 121:

• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Near Chicago Greater Rockford Airport (RFD) – daily rates averaging C$ 115:

• Alamo
• Enterprise Rent-A-Car
• Budget
• Avis
• National

Flights from New York to Chicago may depart from several airports in New York area, including Newark (EWR), New York John F Kennedy Intl (JFK) and New York LaGuardia (LGA), with arrivals available at airports in Chicago area airports such as Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

Morning flights have the fewest delays on this route, while night departures tend to have the most.

A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the New York to Chicago route, 17% of flights were delayed in the past three months, with delays averaging 2h 48m.

One-stop flights from New York to Chicago most commonly connect through:

• Atlanta Hartsfield-Jackson (ATL) – 46% of one-stop connections
• Detroit Metropolitan Wayne County (DTW) – 19% of one-stop connections
• Orlando (MCO) – 9% of one-stop connections
• Washington, D.C. Reagan-National (DCA) – 7% of one-stop connections

Yes. Flexible dates can save you up to 17% on flights from New York to Chicago. Saturday is the cheapest departure day at C$ 363 round-trip on average, while Monday is the most expensive at C$ 435, a difference of C$ 72.

Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

4 airlines operate flights between New York and Chicago. The airlines offering direct flights on this route include:

• United Airlines
• American Airlines
• Delta
• Southwest

Flying via Indianapolis (IND) gives the shortest average 1-stop total travel time at 4h 13m, compared with 4h 22m via Pittsburgh (PIT) and 4h 36m via Detroit Metropolitan Wayne County (DTW).

Chicago is 1 hour behind New York (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

Some of the most popular sights in Chicago are Magnificent Mile, River North, and Grant Park. These are among the most viewed places in Chicago on KAYAK.

Among airlines operating New York to Chicago flights:

• United Airlines: offers extra legroom; offers free seat selection
• American Airlines: offers extra legroom; offers free seat selection
• Delta: offers extra legroom; offers free seat selection
• Southwest: offers free seat selection
• JetBlue: offers extra legroom; offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

Here are some options for this route, based on selected ticket types and cabin classes:

• United Airlines: a carry-on bag and a checked bag in Economy Class
• American Airlines: a carry-on bag and a checked bag in Economy Class
• Delta: a carry-on bag and a checked bag in Economy Class

Baggage allowance can vary by ticket type, cabin class, route, and airline, so always check the fare details before booking.

Chicago Midway is closer to downtown Chicago, and since it is a smaller airport it can be less busy and easier to navigate; however, because of the airport size difference, Chicago O'Hare International tends to have more flights and is served by more carriers.

Rides start at $38 but can, of course, be higher depending on the time of day and traffic conditions.

Chicago O'Hare International utilizes a cell phone lot for those wishing to pick up arriving passengers. The lot has a flight information display to let those waiting know when you have arrived. The airport does not allow stopping in front of the terminal except for immediate pickup of passengers, so the cell phone lot is an excellent option for those waiting for arriving passengers.

One very convenient and unique way to get to New York LaGuardia is via the New York City Ferry. You can take the ferry from New York to the last stop at Astoria and then get a taxi or Uber to the airport. The ferry offers alcoholic and non-alcoholic drinks as well as a variety of snacks on board, making it a comfortable journey overall.