Cheap flights from New York to Chicago

Ready for that fun filled vacation from New York to Chicago? Let Skyscanner help you find the best route and the cheapest airfare between these two mega cities. New York has three airports to depart from and Chicago has two to welcome you. With all these routes, it makes sense to get a little online help. Check out hotel and car rental deals while you're at it.

Best time to Book a Flight to Chicago

Chicago is busiest between April and August. You can usually save money, even during the summer, by flying Tuesdays through Thursdays. Skyscanner's Whole Month Search program comes in handy. Pull up an entire month's airfares to see which dates have the cheapest rates. Find a great rate? Book it, the earlier the better. Being flexible on your travel dates can save you money.

Airlines that Fly from New York to Chicago

Spirit Airlines tends to have the cheapest fares, leaving from La Guardia and arriving into Chicago O'Hare. American Airlines also flies this route. Both carriers offer non-stop service. JetBlue and Delta Airlines are competitively priced out of Kennedy Airport, Both airlines sell code share tickets, where you purchase a fare from one carrier and fly at least one flight on a partner carrier. JetBlue, for example, code shares with Spirit Airlines so you could fly to Chicago out of La Guardia and back into Kennedy. This route is not only a code share, but an open jaw, flying out of one airport and back into another. Non-stops are still the norm. Southwest Airlines, also offering non-stops, tends to fly into Chicago Midway from either New York airport.

Departure Airports in New York

La Guardia International (LGA) is 26 kilometres from Manhattan, about an hour's drive. Taxis can run upwards of $70.00 CAD, while the Airport Shuttles are roughly half that if you book them round trip. Domestic flights leave from both the North and South Terminals.

John F. Kennedy International (JFK) is 29 kilometres from downtown and roughly a $90.00 CAD taxi ride. Shuttle rates are a bit more than from La Guardia. JFK has six operating terminals. Your flight could leave from any of them except Terminal 4, which is dedicated to international flights.

Newark International (EWR) is technically in New Jersey. It's about 25 kilometres from Manhattan, about a $70.00 CAD taxi ride. Shuttle rates are similar to those at La Guardia. Flights to Chicago may leave from any of its three terminals.

All three airports offer free Wi-Fi, a selection of name-brand and local shops, restaurants, fast food outlets and plenty of ATMs.

Arrival Airports in Chicago

Passengers arriving at Chicago Midway will find themselves about 13 kilometres from downtown Chicago, which is about a 30-minute drive. A taxi ride to downtown runs about $40.00 CAD, while the CTA "L" Train Orange Line can get you there for about $5.00 CAD. Midway has one Main Terminal with three concourses. Depending on your airline, you could end up at any one of them.

Chicago O'Hare International is much larger and about 29 kilometres from downtown. Domestic flights use three out of the four terminals. A taxi ride costs about $55.00 CAD into downtown, depending on the distance. The CTA Blue Line connects all three domestic terminals and gets you downtown for about $5.00 CAD.

Both airports have their share of restaurants, delis, fast food outlets, boutique shops and sundry stores. O'Hare has a much larger selection. ATMs are found throughout both airports. Wi-Fi is free.

What to See and Do in Chicago

Deep dish Chicago pizza. Fully loaded all-beef hot dogs in steamed poppy-seed buns. Both are not-to-be-missed delights. Chicago is a city of both fun and sophistication. Millenium Park is a perfect blend of both. This open green space is filled with shops, art displays and has its own theatre and ice rink. Navy Pier, a 1,200-metre long structure jutting out from the Chicago shoreline, features restaurants, carnival rides, shops and regular fireworks shows.

Downtown you'll find The Art Institute of Chicago, home to works by Monet, Gauguin, Picasso and more. A few blocks away is the Chicago Tribune building. Embedded along its outer walls are bits of history, including a piece of the Berlin Wall, a chunk of the Taj Mahal and relics from each of the 50 States.

Interested in dinosaurs? The Field Museum of Natural History has the largest skeleton of a T-Rex ever found. Next door, the Shedd Aquarium features creatures from around the globe, displayed in recreated natural habitats. For a bird's eye view of Chicago and beyond, head for the Hancock Building. The observation deck sits more than 320 metres above the city streets below.