$164 Find Cheap Flights from New York to Chicago – Compare and Save

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.

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
• JetBlue: offers extra legroom; offers free seat selection
• Southwest: offers free seat selection

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

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

• United Airlines
• American Airlines
• Delta
• Southwest
• JetBlue

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 such as Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

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

• United Airlines: a cabin bag and a checked bag in Economy class
• American Airlines: a cabin bag and a checked bag in Economy class
• Delta: a cabin bag and a checked bag in Economy class

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

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

On this route, stopover flights are cheaper than direct options on average. Stopover fares average $253 return via Fort Lauderdale (FLL), compared with $344 for direct.

There is no standard. Checked bag policies vary by airline on this route. Most carriers charge $48–$139 for the first checked bag in Economy. Premium fares and elite status bookings typically include a free checked bag.

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

• Atlanta Hartsfield-Jackson (ATL) – 50% of one-stop connections
• Detroit Metropolitan Wayne County (DTW) – 17% of one-stop connections
• Fort Lauderdale (FLL) – 9% of one-stop connections
• Orlando (MCO) – 7% of one-stop connections

Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

On the New York to Chicago route, being flexible with your departure day can save you up to 17%. Saturday is the cheapest day at $320 return on average, while Monday is the most expensive at $385 – a $65 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

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 3 months, with delays averaging 2 hours 49 minutes.

Morning is the busiest departure period on New York to Chicago flights, with 46% leaving in that window. Afternoon departures account for 27%, Evening flights for 23%, and Night flights for 4%.

Some of the most popular sights in Chicago are River North, Chicago Water Tower, and Union Station. These are among the most viewed places in Chicago on KAYAK.

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

• Earliest: departs at 05:23 and lands at 08:10
• Latest: departs at 23:00 and lands at 01:47.

The flight takes about 2h 47m.

Last-minute fares on this route (booked within 2 weeks of departure) run 31% above the route average of $343. Book 7 weeks before departure for the lowest fares.

A direct flight from New York to Chicago takes 2h 47m, covering 1,841 km.

No. A passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

Yes. Based on fares seen in the past 5 days, return flight prices on this route showed a wide range, from about $333 to $3,237. That means the highest observed fare was about 10x higher than the lowest one.

One-way fares from New York to Chicago are currently lower than usual. Average one-way flight prices are about $204, which is 17% below the typical average for this route.

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: 84% on time

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

Morning flights have the fewest delays on this route. Delays tend to pile up throughout the day as one late flight pushes the next, so earlier departures are usually more reliable.

Based on prices from the last 5 days, flying between New York and Chicago is around $333 return, with a flight time of about 12h 15m. Taking the train is much cheaper at around $313, with a trip time of about 28h 23m. The bus is similarly priced at around $249 and takes about 22h 24m. Compared to flying, recent train and bus fares are roughly 16% lower. However, those options take about 13+ hours longer each way.

Flying via Indianapolis (IND) gives the shortest average 1-stop total travel time of 4h 13m, compared to 4h 14m via Detroit Metropolitan Wayne County (DTW) and 4h 21m via Cincinnati Cinci./N. Kentucky (CVG).

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

Since Chicago is served by multiple airports, car hire options and rates can vary depending on which one you fly into.
Near Chicago O'Hare Intl Airport (ORD) – daily rates from around $24:

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

Near Chicago Midway Airport (MDW) – daily rates from around $45:

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

Near Chicago Greater Rockford Airport (RFD) – daily rates from around $42:

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

Return flights from New York to Chicago range from $242 to $482, with an average of $343 over the past 12 months. Anything below $242 counts as a good deal.

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

• • American Airlines
• • Delta
• • JetBlue