Flights from New York to Chicago. Use Google Flights to plan your next trip and find cheap one way or round trip flights from New York to Chicago.Cheap Flights from Chicago to New York (MDW-JFK) Prices were available within the past 7 days and start at $124 for one-way flights and $239 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. Book one-way or return flights from Chicago to New York with no change fee on selected flights.Wed, 30 Oct JFK - ORD with Delta. Direct. from £128. New York. £131 per passenger.Departing Wed, 1 May, returning Wed, 8 May.Return flight with jetBlue.Outbound direct flight with jetBlue departs from Chicago O'Hare International on Wed, 1 May, arriving in New York John F. Kennedy.Inbound direct flight with jetBlue departs from New York …Cheap Flights from Chicago to New York (MDW-LGA) Prices were available within the past 7 days and start at $48 for one-way flights and $96 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. Book one-way or return flights from Chicago to New York with no change fee on selected flights.On average, a flight to Chicago O'Hare Intl Airport costs $411. The cheapest price found on KAYAK in the last 2 weeks cost $33 and departed from Atlanta. The most popular routes on KAYAK are New York to Chicago O'Hare Intl Airport which costs $282 on average, and Boston to Chicago O'Hare Intl Airport, which costs $395 on average.Use our Low Fare Calendar to find the lowest fares on flights to New York (LaGuardia) available inside your travel window. Find flights. Central Park. The High Line. Washington Square Park. Ellis Island. One World Trade Center. The Metropolitan Museum of Arts. Rockefeller Center. The cheapest month for flights from New York to Chicago Midway Airport is April, where tickets cost $205 on average. On the other hand, the most expensive months are May and July, where the average cost of tickets is $488 and $438 respectively. Book cheap flights to New York/Newark (EWR) with United Airlines. ... New York City is synonymous with great cuisine, entertainment, culture, ... From Chicago (ORD) To New York/Newark (LGA) Roundtrip | Economy: 05/29/24 - 05/29/24: from. $ 117* Viewed: 1 day ago. From West Palm Beach (PBI) Located just 14 miles from Manhattan, Newark Liberty International Airport offers the fastest surface transfer journeys to many parts of the city, including the AirTrain service to New York Penn Station in midtown Manhattan, with a journey time of less than 30 minutes. Flights from Chicago to New York. Use Google Flights to plan your next trip and find cheap one way or round trip flights from Chicago to New York. Find the best flights... Cheap Flights from Chicago to New York (CHI-NYC) Prices were available within the past 7 days and start at $31 for one-way flights and $61 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. Book one-way or return flights from Chicago to New York with no change fee on selected flights. Wed, 30 Oct JFK - ORD with Delta. Direct. from £128. New York. £131 per passenger.Departing Wed, 1 May, returning Wed, 8 May.Return flight with jetBlue.Outbound direct flight with jetBlue departs from Chicago O'Hare International on Wed, 1 May, arriving in New York John F. Kennedy.Inbound direct flight with jetBlue departs from New York …Cheap Flights from New York to Chicago (NYC-ORD) Prices were available within the past 7 days and start at $31 for one-way flights and $61 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. Book one-way or return flights from New York to Chicago with no change fee on selected flights.from $66. Guadalajara.$69 per passenger.Departing Mon, Nov 4.One-way flight with Viva Aerobus.Outbound direct flight with Viva Aerobus departing from Chicago O'Hare International on Mon, Nov 4, arriving in Guadalajara.Price includes taxes and charges.From $69, select. Guadalajara Mexico. Mon, Nov 4 ORD – GDL with Viva … Flights from Chicago to New York with American Airlines. Round trip. 1 Adult, Economy class. Book with cash. From. To. Depart. 04/29/24. today. Flights to New York John F Kennedy Intl Airport, New York. Find flights to New York John F Kennedy Airport from $59. Fly from Chicago O'Hare Airport on JetBlue, American …Flights from Chicago to New York. Use Google Flights to plan your next trip and find cheap one way or round trip flights from Chicago to New York. Find the best flights...Frequently asked questions about flights from Chicago to New York City. How is COVID-19 currently affecting flights from Chicago to New York City? Using the flexible flight ticket, you're guaranteed a refund or a rebooking option (without fees) in case of flight cancellations when travelling to United States. The cheapest month for flights from New York to Chicago Midway Airport is April, where tickets cost $205 on average. On the other hand, the most expensive months are May and July, where the average cost of tickets is $488 and $438 respectively. Your Chicago to New York flights will arrive into John F Kennedy International (JFK) Airport, 15 miles outside Manhattan. With a flight time of around 2 hours 10 minutes you'll arrive in the Big Apple feeling refreshed and looking forward to your stay.Find the best deals on flights from Chicago O'Hare International (ORD) to New York Newark (EWR). Compare prices from hundreds of major travel ... to Newark Liberty International Airport (EWR). Newark is 15 miles away from New York City, which is home to Broadway shows, fine dining establishments and historical sites. It takes two hours to ...Save time and money when you choose Volaris for your flights to Mexico City! Check-in up to 72 hours in advance, and only pay for options you choose. Find low prices on Mexico City flights with Volaris. Book your flights to Mexico City (MEX), Mexico from over 65 cities in the Americas.Cheap Flights from New York to Chicago (NYC-CHI) Prices were available within the past 7 days and start at $31 for one-way flights and $57 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. Book one-way or return flights from New York to Chicago with no change fee on selected flights.Fill out the Alternative Airlines search form. Choose a return, one way or multi-city search. Enter the airports you want to fly between. Enter the dates you want to fly on. Select the number of travelers and preferred cabin class. Click ' Search Flights '. How to Book Red Eye Flight Tickets. Use the 'Times' filter.Concept for the 2024 Paris Olympics. Summary. Get to the Paris Olympics from major U.S. cities for less than $1,000 round trip. Enjoy quick layovers in top …Mon, Jun 3 EWR – CID with Spirit Airlines. 1 stop. from $194. New York.$206 per passenger.Departing Thu, May 2, returning Sun, May 5.Round-trip flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departing from Cedar Rapids on Thu, May 2, arriving in New York LaGuardia.Inbound indirect flight with Frontier Airlines ...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.Flights to New York John F Kennedy Intl Airport, New York. Find flights to New York John F Kennedy Airport from $59. Fly from Chicago O'Hare Airport on JetBlue, American … There are 5 airlines that fly nonstop from New York to Chicago O'Hare Intl Airport. They are: American Airlines, Delta, JetBlue, Spirit Airlines and United Airlines. The cheapest price of all airlines flying this route was found with Spirit Airlines at $42 for a one-way flight. On average, the best prices for this route can be found at Spirit ... The cheapest month for flights from New York to Chicago Midway Airport is April, where tickets cost $205 on average. On the other hand, the most expensive months are May and July, where the average cost of tickets is $488 and $438 respectively. Looking for a cheap flight? 25% of our users found tickets from Chicago O'Hare Airport to the following destinations at these prices or less: New York $94 one-way - $136 round-trip. Morning departure is around 10% more expensive than an evening flight, on average*. *Average of the lowest prices shown in KAYAK’s search results for departures ... Cheap Flights from New York to Chicago (LGA-ORD) Prices were available within the past 7 days and start at $27 for one-way flights and $53 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. Book one-way or return flights from New York to Chicago with no change fee on selected flights. JetBlue offers flights to 90+ destinations with free inflight entertainment, free brand-name snacks and drinks, lots of legroom and award-winning service.Direct. from $59. Chicago.$60 per passenger.Departing Tue, Jun 4, returning Wed, Jun 12.Round-trip flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departing from New York LaGuardia on Tue, Jun 4, arriving in Chicago O'Hare International.Inbound direct flight with Spirit Airlines departing from Chicago O'Hare ...ORD - Chicago O'Hare International - Main Garage, Chicago, IL 60666, USA View Airport. Charter to Chicago. Private jet from Chicago to New Orleans. Private jet from Chicago to Ningbo. With BLADE's renowned jet charter service, you can fly between Chicago and New York City and enjoy unmatched travel experience.Book one-way or return flights from Chicago to New York starting at $26. Fly with top airlines and search for flights deals on Trip.com now!Book one-way or return flights from Chicago to New York starting at $26. Fly with top airlines and search for flights deals on Trip.com now!The usual cost for a one-way flight to Newark Airport is around $20, while a round-trip averages at about $35. Usually, a round-trip ticket to New York costs in the vicinity of $225, but there are deals as low as $73. If time is of the essence, the quickest one-way flight to New York departs from Ithaca with an average duration of 0 hours 21 ...An off-duty Chicago cop was shot and killed as he came home from work early Sunday in what the police superintendent called “another sad day” for the Windy City.Direct. from $59. Chicago.$60 per passenger.Departing Tue, Jun 4, returning Wed, Jun 12.Round-trip flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departing from New York LaGuardia on Tue, Jun 4, arriving in Chicago O'Hare International.Inbound direct flight with Spirit Airlines departing from Chicago O'Hare ...Our data shows that the cheapest route for a one-way flight from Chicago to Newark Airport cost $89 and was between Chicago O'Hare Intl Airport and Newark Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $168.Round-trip. 1 adult. Economy. Round-trip One-way Multi-city. From? To? Thu 4/18. Thu 4/25. 1 adult. Economy. Find Your Flight. The best prices from Chicago to …On average, a flight to Chicago O'Hare Intl Airport costs $411. The cheapest price found on KAYAK in the last 2 weeks cost $33 and departed from Atlanta. The most popular routes on KAYAK are New York to Chicago O'Hare Intl Airport which costs $282 on average, and Boston to Chicago O'Hare Intl Airport, which costs $395 on average. Cheap Flights from New York to Chicago (NYC-ORD) Prices were available within the past 7 days and start at $31 for one-way flights and $61 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. Book one-way or return flights from New York to Chicago with no change fee on selected flights. Mon, Jun 3 EWR – CID with Spirit Airlines. 1 stop. from $194. New York.$206 per passenger.Departing Thu, May 2, returning Sun, May 5.Round-trip flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departing from Cedar Rapids on Thu, May 2, arriving in New York LaGuardia.Inbound indirect flight with Frontier Airlines ...Fly from Chicago O'Hare Airport to New York on Spirit Airlines from $25... Search for New York flights on KAYAK now to find the best deal.Cheap Flights from Houston to New York (HOU-NYC) Prices were available within the past 7 days and start at $46 for one-way flights and $91 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. Book one-way or return flights from Houston to New York with no change fee on selected flights.Tue, Jun 4 LGA – ORD with Spirit Airlines. Direct. Wed, Jun 5 ORD – LGA with Spirit Airlines. Direct. from $59. Chicago.$60 per passenger.Departing Tue, May 7, returning Wed, May 8.Round-trip flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departing from New York LaGuardia on Tue, May 7, arriving in Chicago O'Hare ...Your Chicago to New York flights will arrive into John F Kennedy International (JFK) Airport, 15 miles outside Manhattan. With a flight time of around 2 hours 10 minutes you'll arrive in the Big Apple feeling refreshed and looking forward to your stay.Round-trip. 1 adult. Economy. Round-trip One-way Multi-city. From? To? Thu 4/18. Thu 4/25. 1 adult. Economy. Find Your Flight. The best prices from Chicago to … Located just 14 miles from Manhattan, Newark Liberty International Airport offers the fastest surface transfer journeys to many parts of the city, including the AirTrain service to New York Penn Station in midtown Manhattan, with a journey time of less than 30 minutes. Cheap Flights from Chicago to New York (CHI-LGA) Prices were available within the past 7 days and start at $31 for one-way flights and $61 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. Book one-way or return flights from Chicago to New York with no change fee on selected flights.Southwest Flights From Chicago to New York. Southwest operates around 56 flights from Chicago to New York every week. The average price of these flights found in the last 72 hours has been $389, but momondo users have found Southwest deals from Chicago to New York from as low as $288 round-trip. Southwest has been scored …Find Ultra Low Fares from Chicago to New York. Fly with Spirit Airlines and get a great deal on flights from Chicago to New York. With Spirit's Bare Fare™ You Pay Only the Services You Need!The cheapest way to get from Chicago to New York costs only $106, ... Flights from Chicago O'Hare to New York La Guardia Ave. Duration 2h 11m When Every day Estimated price $110 - $ ... entertainment center and neighborhood in the Midtown Manhattan section of New York City at the junction of Broadway and Seventh Avenue. Whether you’re exploring the excellent museums, taking in some theatre, shopping, or seeing the famous Statue of Liberty and Empire State Building, the city that never sleeps has got something for the whole family! Fly more and save even more when you travel to New York City, NY (LGA) with Frontier where you always find low fares done right. Wed, 8 May ORD - LGA with Spirit Airlines. Direct. from $89. Chicago.$94 per passenger.Departing Tue, 4 Jun, returning Wed, 5 Jun.Return flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from New York LaGuardia on Tue, 4 Jun, arriving in Chicago O'Hare International.Inbound direct flight with Spirit Airlines ...Cheapest round-trip prices found by our users on KAYAK in the last 72 hours. One-way Round-trip. New York nonstop $49. Buffalo 1 stop $97. Syracuse 1 stop $97. Rochester nonstop $242. Albany nonstop $159. Ithaca 1 stop $238. Binghamton 1 stop $276.The cheapest flights to John F. Kennedy Intl. found within the past 7 days were $111 round trip and $59 one way. Prices and availability subject to change. Additional terms may apply. Tue, May 7 - Tue, May 7. ORD. Chicago. JFK. New York. $111.Wed, 15 May ORD - LGA with Spirit Airlines. Direct. from £47. Chicago. £48 per passenger.Departing Tue, 4 Jun, returning Wed, 12 Jun.Return flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from New York LaGuardia on Tue, 4 Jun, arriving in Chicago O'Hare International.Inbound direct flight with Spirit Airlines ...Detailed flight information from Chicago ORD to New York LGA. See all airline(s) with scheduled flights and weekly timetables up to 9 months ahead. Flightnumbers and complete route information. The cost to charter a private jet from Chicago to NYCstarts at around $10,000* for one-way flight in a light jet ( Cessna Citation V, Hawker 400XP, Phenom 300 ); $16,000* for a midsize jet ( Challenger 300, Citation Excel XLS, Hawker 800XP ); and $20,000* for a heavy jet ( Challenger 604, Gulfstream G4, Gulfstream G550 ). Find the cheapest month to fly from Chicago O'Hare International to New York. We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago O'Hare International to New York flights are currently cheapest in May. Apr. from $148. Chicago, IL is 711 miles from New York City. There are 64 daily flights from Chicago, IL to New York City. There are 109 weekly flights from Chicago, IL to New York City. 74 non-stop flights are operating from Chicago, IL to New York City today. United Airlines has the most nonstop flights between Chicago, IL and New York City. Cheap Flights from Chicago to New York (CHI-NYC) Prices were available within the past 7 days and start at $31 for one-way flights and $61 for round trip, for the period …Flights to New York John F Kennedy Intl Airport, New York. Find flights to New York John F Kennedy Airport from $59. Fly from Chicago O'Hare Airport on JetBlue, American …Deal found 4/12 $337. Pick Dates. JetBlue is one of the most popular airlines used for those traveling from Chicago to New York. Flights on this route from JetBlue typically cost $225.27 RT, a price that is 56% cheaper than the average Chicago to New York flight. The cheapest flight found was $58 RT.Roundtrip. One way. Multi-city. Direct flights only. Origin. Destination. Departure. Return. Passengers. Search Flight + Hotel. Search flights. Last minute flights from Chicago to … Flights from Chicago to New York with American Airlines. Round trip. 1 Adult, Economy class. Book with cash. From. To. Depart. 04/29/24. today. Discover our best United flight from Chicago ORD to New York JFK. To find the best deals on flights to Chicago from New York with United, just enter your travel dates, filter by United, and hit search. You’ll find flights to choose from and can sort by price, flight duration, and arrival or departure time.Amtrak. The best round-trip train deal from Chicago to New York found on momondo in the last 72 hours is $184. The best one-way train deal from Chicago to New York found on momondo in the last 72 hours is $92. Average time it takes to travel by train from Chicago to New York. There is 1 train company servicing this route: Amtrak.Find the best deals on flights from Chicago O'Hare International (ORD) to New York Newark (EWR). Compare prices from hundreds of major travel ... to Newark Liberty International Airport (EWR). Newark is 15 miles away from New York City, which is home to Broadway shows, fine dining establishments and historical sites. It takes two hours to ...Yes, there are multiple flights from New York to Chicago for under $100. The cheapest flight booked recently is on Spirit Airlines for just $55, but on average you can expect to pay $71. Are there nonstop flights from New York to Chicago for under $100 on Cheapflights? Cheapflights has at least 20 direct flights from New York to Chicago …Round-trip tickets start from $114 and one-way flights to New York John F. Kennedy from Chicago O'Hare International start from $57 Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.Apr 17, 2024 · Find airfare and ticket deals for cheap flights from Chicago, IL to New York, NY. Search flight deals from various travel partners with one click at $30. Among the airport’s most-traveled routes: New York City, London, Los Angeles and San Francisco. Show more Because of the number of Southwest Airlines flights, Midway International Airport (MDW) is known for its cheap airfares.Cheap Flights from Chicago to New York (MDW-JFK) Prices were available within the past 7 days and start at $124 for one-way flights and $239 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. Book one-way or return flights from Chicago to New York with no change fee on selected flights.How much is the cheapest flight to New York? Prices were available within the past 7 days and start at $45 for one-way flights and $48 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. Find cheap return or one-way flights to New York. Book & compare flight deals to New York and save ...Cheap Flights from Dallas to New York (DFW-NYC) Prices were available within the past 7 days and start at $44 for one-way flights and $88 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. Book one-way or return flights from Dallas to New York with no change fee on selected flights.Among the airport’s most-traveled routes: New York City, London, Los Angeles and San Francisco. Show more Because of the number of Southwest Airlines flights, Midway International Airport (MDW) is known for its cheap airfares.Cheap Flights from Dallas to New York (DFW-NYC) Prices were available within the past 7 days and start at $44 for one-way flights and $88 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. Book one-way or return flights from Dallas to New York with no change fee on selected flights.Direct. Tue, Jun 11 LGA – ORD with Spirit Airlines. Direct. from $60. New York.$60 per passenger.Departing Tue, May 21, returning Tue, Jun 4.Round-trip flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departing from Chicago O'Hare International on Tue, May 21, arriving in New York LaGuardia.Inbound direct flight with ...Direct. from ₹ 2,474. New York. ₹ 3,568 per passenger.Departing Wed, 23 Oct.One-way flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Chicago O'Hare International on Wed, 23 Oct, arriving in New York LaGuardia.Price includes taxes and charges.From ₹ 3,568, select. Wed, 23 Oct ORD - LGA with Spirit Airlines. Our data shows that the cheapest route for a one-way flight from Chicago to New York John F Kennedy Intl Airport cost $69 and was between Chicago O'Hare Intl Airport and New York John F Kennedy Intl Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $107. Southwest Flights From Chicago to New York. Southwest operates around 56 flights from Chicago to New York every week. The average price of these flights found in the last 72 hours has been $389, but momondo users have found Southwest deals from Chicago to New York from as low as $288 round-trip. Southwest has been scored …Frequently asked questions about flights from Chicago to New York City. How is COVID-19 currently affecting flights from Chicago to New York City? Using the flexible flight ticket, you're guaranteed a refund or a rebooking option (without fees) in case of flight cancellations when travelling to United States. Located just 14 miles from Manhattan, Newark Liberty International Airport offers the fastest surface transfer journeys to many parts of the city, including the AirTrain service to New York Penn Station in midtown Manhattan, with a journey time of less than 30 minutes. Flights from New York to Chicago with American Airlines. Round trip. 1 Adult, Economy class. Book with cash. From. To. Depart. 04/30/24. today.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.Cheapest round-trip prices found by our users on KAYAK in the last 72 hours. One-way Round-trip. New York nonstop $49. Buffalo 1 stop $97. Syracuse 1 stop $97. Rochester nonstop $242. Albany nonstop $159. Ithaca 1 stop $238. Binghamton 1 stop $276.
Cheap Flights from Chicago to New York (CHI-NYC) Prices were available within the past 7 days and start at $31 for one-way flights and $61 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. Book one-way or return flights from Chicago to New York with no change fee on selected flights. . Mydish.com en espanol
Use Google Flights to plan your next trip and find cheap one way or round trip flights from Chicago to anywhere in the world.Compare cheap flights and find tickets from Chicago (CHI) to New York (NYC). Book directly with no added fees.The 805-mile road trip from Chicago to New York City can be done in a little over 12 hours of pure driving but you will want to take a few days and stop along the Great Lakes, in Pittsburgh, Philadelphia and visit beautiful National Parks on the way. Read on to find out exactly which route to take, the best places and sights to see along the ... Cheap Flights from Chicago to New York (ORD-NYC) Prices were available within the past 7 days and start at $31 for one-way flights and $61 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. Book one-way or return flights from Chicago to New York with no change fee on selected flights. Direct. from ₹ 2,474. New York. ₹ 3,568 per passenger.Departing Wed, 23 Oct.One-way flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Chicago O'Hare International on Wed, 23 Oct, arriving in New York LaGuardia.Price includes taxes and charges.From ₹ 3,568, select. Wed, 23 Oct ORD - LGA with Spirit Airlines.Looking for a cheap flight? 25% of our users found tickets from Chicago O'Hare Airport to the following destinations at these prices or less: New York $94 one-way - $136 round-trip. Morning departure is around 10% more expensive than an evening flight, on average*. *Average of the lowest prices shown in KAYAK’s search results for departures ... Sun, 28 Jul LGA - MDW with Frontier Airlines. 1 stop. from £190. New York. £239 per passenger.Departing Wed, 8 May, returning Tue, 14 May.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Wed, 8 May, arriving in New York Newark.Inbound indirect flight with Delta, departs from New York Newark on Tue ... There are 3 airlines that fly nonstop from Chicago to London. They are: American Airlines, British Airways and United Airlines. The cheapest price of all airlines flying this route was found with United Airlines at $572 for a one-way flight. On average, the best prices for this route can be found at United Airlines.Chicago to New York City Flights. Flights from MDW to LGA are operated 32 times a week, with an average of 5 flights per day. Departure times vary between 05:35 - 20:20. The earliest flight departs at 05:35, the last flight departs at 20:20. However, this depends on the date you are flying so please check with the full flight schedule above to ...Yes, there are multiple flights from New York to Chicago for under $100. The cheapest flight booked recently is on Spirit Airlines for just $55, but on average you can expect to pay $71. Are there nonstop flights from New York to Chicago for under $100 on Cheapflights? Cheapflights has at least 20 direct flights from New York to Chicago …Our data shows that the cheapest route for a one-way flight from Chicago Midway Airport to New York cost $494 and was between Chicago Midway Airport and New York LaGuardia Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $332..