Cheap Flights from New York (NYC) to Chicago (CHI)

Top tips for finding a cheap flight from New York to Chicago

Finding cheap tickets from New York to Chicago is easy with a little flexibility. Use our Whole Month search feature to scan through the calendar for the cheapest dates. You can also set up a Price Alert for your route and let us monitor the fares for you, sending notifications when prices change. If you’d rather skip layovers, select the Direct Flights search to view non-stop options that’ll save you time.

Booking your tickets early often leads to savings, but we can also find you some last-minute deals. In general, January is the best time to schedule your trip from New York to Chicago, with the lowest average fares across the board. Keep these strategies in mind to find the best itinerary.

Handy information about New York airport

New York hosts a selection of airports, each serving a variety of destinations and offering multiple transportation options to ensure your transit to and from the city is as smooth as possible. LaGuardia Airport features four terminals, with Terminals A and B handling mainly domestic flights and Terminal D catering to both international and domestic routes. Transportation from LaGuardia includes a range of options from taxis and buses to the subway connecting M60 SBS bus.

John F. Kennedy International Airport, the city's conduit for extensive international travel, comprises six terminals where Terminal 1 and Terminal 4 are focal points for international carriers, while Terminals 5 and 8 accommodate both domestic and international flights. To navigate to the city or connecting flights, JFK offers the AirTrain service along with buses and taxis. Newark Liberty International Airport, serving both domestic and international flights across three terminals, provides the convenience of AirTrain Newark and NJ Transit trains, aside from the usual car services and taxis. For a more low-key departure or arrival, Stewart International Airport, with its single terminal, offers primarily domestic flights with a few international routes seasonally, accessible via car services and taxis.

Chicago airport: good to know

Chicago caters to a broad range of air travel needs through its diverse array of airports. Chicago O'Hare International Airport, one of the world's largest airports, boasts four terminals, providing numerous ground transport options including the CTA "L" train, connecting passengers to virtually anywhere in the city. It serves a wide range of domestic and international destinations, with a dedicated terminal for international travelers.

Complementing O'Hare, Chicago Midway International Airport operates from one terminal with three concourses and ensures connectivity with various ground transportation modes, focusing primarily on domestic flights and a few international routes. For more personalized travel, both Chicago Executive and DuPage Airports offer a terminal each for private and corporate aircraft, alongside convenient transport services. Lastly, Chicago Rockford, despite its single terminal structure, supports domestic travel, particularly catering to budget-conscious passengers. Each airport, strategically located, makes accessible the vast metropolitan landscape and aligns with different travel preferences, maintaining Chicago's reputation as a significant transportation hub. Knowing how far the airport is from your accommodation and the best way to get there will help keep your journey stress-free when flying from New York to Chicago.

Best time to fly from New York to Chicago

The best time to fly from New York to Chicago is during the spring (March to May) and fall (September to November), when you can enjoy moderate temperatures ranging from 43°F to 68°F. These seasons offer comfortable weather, making it ideal for exploring the city without the extreme cold of winter or the occasional heat waves of summer. Visiting during these times also means experiencing Chicago's city life and attractions in a more temperate climate.

Reasons to visit Chicago

When planning your trip to Chicago, check out these activities and attractions the city has to offer. Tap into the energy of Lollapalooza, a celebrated music festival that draws fans and top artists alike for an unforgettable experience. Rise above the city streets at the Willis Tower Skydeck to capture expansive views from one of the tallest buildings in the world. Find a moment of tranquility as you stroll through Millennium Park and gaze upon the renowned public art and architecture. Not to be missed, The Art Institute of Chicago houses a vast collection that spans thousands of years, offering insights into humanity's creative legacy.

Add hotel bookings and car hire to your New York to Chicago flight

Planning your trip to Chicago is easy and convenient with Skyscanner. Find the perfect vehicle for your stay from trusted rental car brands like Budget, Europcar, and Thrifty. Accommodation choices are plentiful; choose from well-known hotels such as The Palmer House Hilton, Hyatt Regency Chicago, or InterContinental Chicago Magnificent Mile, an IHG Hotel. Skyscanner helps you organize both your travel and comfortable stay in the Windy City.