Cheap Flights from New York Newark (EWR) 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, February 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 serves as a gateway to the world with multiple airports, including Newark Liberty International Airport in New Jersey. Newark, just a short journey from the heart of New York City, has three terminals handling a variety of domestic and international routes. Terminal A caters to both international and domestic travelers with convenient access to AirTrain Newark and a selection of car rental agencies. Terminal B operates a mix of domestic and international flights, similarly offering AirTrain Newark and car rental services to facilitate your onward journey. For those departing or arriving at Terminal C, a similar range of flights is available, complemented by robust ground transportation options, including AirTrain Newark, car rentals, and taxi services. Each terminal at Newark ensures that visitors can connect to their destinations with facilities designed to cater to a wide range of travel needs.

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. Arrange your airport transfers ahead of time when traveling from New York to Chicago for a stress-free arrival.

Best time to fly from New York to Chicago

The best time to fly from New York to Chicago is during the transitional seasons of spring and fall. The pleasant temperatures range between 42.8°F to 68°F, ideal for exploring the Windy City comfortably. March to May and September to November are the optimal months to visit, allowing you to avoid the extreme cold of the winter and the occasional heat waves of the summer. Whether you're attending a business conference or enjoying the city's diverse attractions, these moderate months provide the most agreeable weather for your travel plans.

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.