MIA. Miami Intl. $53. Roundtrip. just found. Cheap flights from Chicago , IL to all destinations. Find best deals for flights from Chicago , IL from top airlines with great prices at Expedia.com. The cheapest return flight ticket from New York to Chicago found by KAYAK users in the last 72 hours was for C$ 161 on Delta, followed by Spirit Airlines (C$ 254). One-way flight deals have also been found from as low as C$ 69 on Frontier and from C$ 70 on Spirit Airlines. 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.Compare cheap flights and find tickets from Chicago (CHI) to New York (NYC). Book directly with no added fees.Chicago. New York. Compare Chicago to New York flight deals. Find the cheapest month or even day of the year to fly to New York. Book the best New York … The two airlines most popular with KAYAK users for flights from New York to Chicago are Alaska Airlines and Delta. With an average price for the route of $319 and an overall rating of 8.1, Alaska Airlines is the most popular choice. Delta is also a great choice for the route, with an average price of $276 and an overall rating of 8.0. 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 ...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.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!Our data shows that the cheapest route for a one-way flight from New York to Chicago O'Hare Intl Airport cost $42 and was between New York LaGuardia Airport and Chicago O'Hare 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 $74.Wed, Nov 20 MEX – ORD with Viva Aerobus. Direct. from $223. Mexico City.$232 per passenger.Departing Sat, Nov 16, returning Thu, Dec 5.Round-trip flight with Viva Aerobus.Outbound direct flight with Viva Aerobus departing from Chicago O'Hare International on Sat, Nov 16, arriving in Mexico City Juarez International.Inbound direct …Detailed flight information from Chicago ORD to New York JFK. See all airline(s) ... The airlines below are departing from or arriving to other airports in the same city or very close. Southwest Airlines. ... Airlines with direct flights from Chicago to New York in the past. Iberia. Oneworld Last flight was scheduled 2018-05-31Tue, 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 ...Cheapest flights to United Kingdom from New York. New York to London from $309. Price found Apr 18, 2024, 6:28 AM. New York to Manchester from $427. Price found Apr 18, 2024, 6:28 AM. New York to Edinburgh from $448. Price found Apr 19, 2024, 10:03 AM. New York to Birmingham from $466.Fly Emirates to New York (NYC) and beyond. Get inspired by our recommended destinations and book your next flight or holiday today. And on your way, enjoy superior comfort, gourmet meals and award-winning entertainment with us, whether you’re flying in Economy Class, Premium Economy, Business Class or First Class. Flights to Milan. How long is the flight from Chicago to New York? The flight time from Chicago to New York is 2 hours, 4 minutes. The time spent in the air is 1 hour, 37 minutes. These numbers are averages. In reality, it varies by airline with Spirit being the fastest taking 1 hour, 57 minutes, and Delta the slowest taking 2 hours, 6 minutes. 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 between some cities may be significantly cheaper if you choose a multi-stop airline ticket. Although these connecting flights sacrifice some convenience, on average, travelers save 20%-60% when they choose to fly multi-stop versus a direct flight.. The average price for connecting flights from New York City to Chicago is not available.. The average … Chicago (O'Hare), IL to New York (LaGuardia), NY. departing on 9/14. one-way starting at*. $94. Book now. * Restrictions and exclusions apply. Seats and dates are limited. Select markets. 16 travel days available. 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 …Find cheap flights from Chicago to New York. Book the cheapest price and save money with lastminute.com. Call to book. Flight + Hotel. Flash Sales. Holidays. City breaks. Flights. Hotels. ... Cheap flights Mexico City - New York. Departing on Friday, 26 April 2024 and returning on Wednesday, 1 May 2024. from £345 10h ago .Chicago - New York/Newark. Located just 14 miles from Manhattan, Newark Liberty International Airport offers the fastest surface transfer journeys to many parts of …From the populous city of Chicago, Illinois, located in the heart of the country, nonstop flights to New York City can take between 2 hours 7 minutes and 2 hours 24 minutes from Chicago O'Hare International Airport (ORD), with flights that stop in Philadelphia taking around 4 hours.The cheapest way to get from Chicago to New York, NY costs only $109, ... Flights from Chicago O'Hare to New York La Guardia Ave. Duration 2h 11m When Every day Estimated price $110 - $ ... The New York City Subway consists of …Tue, May 21 EWR – BOS with Delta. Direct. from $98. New York.$117 per passenger.Departing Tue, Jun 4, returning Thu, Jun 6.Round-trip flight with Delta.Outbound direct flight with Delta departing from Boston Logan International on Tue, Jun 4, arriving in New York Newark.Inbound direct flight with Delta departing from New York John F. … 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. 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 …Find flights to New York from $37. Fly from Chicago on Spirit Airlines, Frontier and more. Search for New York flights on KAYAK now to find the best deal.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.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 ...Wed, Nov 20 MEX – ORD with Viva Aerobus. Direct. from $223. Mexico City.$232 per passenger.Departing Sat, Nov 16, returning Thu, Dec 5.Round-trip flight with Viva Aerobus.Outbound direct flight with Viva Aerobus departing from Chicago O'Hare International on Sat, Nov 16, arriving in Mexico City Juarez International.Inbound direct …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 ... 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. 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 …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 ...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.Our data shows that the cheapest route for a one-way flight from New York to Chicago O'Hare Intl Airport cost $42 and was between New York LaGuardia Airport and Chicago O'Hare 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 $74.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.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!This time of year offers the best deals on train tickets from Chicago to New York, with the average price at just $227. Train tickets on this route are most expensive in September, when the average price goes up to $305. You can still score cheap deals below this average price, though, especially if you plan ahead and book your ticket in advance. The two airlines most popular with KAYAK users for flights from New York to Chicago are Alaska Airlines and Delta. With an average price for the route of $319 and an overall rating of 8.1, Alaska Airlines is the most popular choice. Delta is also a great choice for the route, with an average price of $276 and an overall rating of 8.0. 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.Are you searching for American Airlines flights from Chicago to New York/Newark? Find the best selections and fly in style. 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 ... 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. Wed, Jul 10 JFK – ORD with jetBlue. Direct. from $126. New York.$126 per passenger.Departing Wed, Aug 14, returning Tue, Aug 20.Round-trip flight with Delta.Outbound direct flight with Delta departing from Chicago O'Hare International on Wed, Aug 14, arriving in New York John F. Kennedy.Inbound direct flight with Delta …How long is the flight to New York City? Whether you are flying from Chicago, IL, Atlanta, Georgia, or Anaheim/Orange County, California, you will be able to convenient, non-stop flights to New York City. When flying from Chicago, a flight will clock in at less than 2h 30m. From Atlanta, the trip will take about the same time. Book the lowest fares on New York flights today! ... Chicago (ORD) to. New York (LGA) 05/29/24 - 06/05/24. ... Oklahoma City - New York; Houston - New York; Chicago ... Our data shows that the cheapest route for a one-way flight from Detroit Metropolitan Wayne County Airport to New York cost $25 and was between Detroit Metropolitan Wayne County 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 $53.Roundtrip. One way. Multi-city. Direct flights only. Origin. Destination. Departure. Return. Passengers. Search Flight + Hotel. Search flights. Last minute flights from Chicago to …Thousands of people held protests across the US on Monday condemning Israel’s attack on Gaza, shutting down airports and disrupting traffic in major cities from … Direct. from £47. New York. £48 per passenger.Departing Wed, 8 May, returning Wed, 15 May.Return flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Chicago O'Hare International on Wed, 8 May, arriving in New York LaGuardia.Inbound direct flight with Spirit Airlines departs from New York LaGuardia on Wed, 15 ... Flying Time 2 h and 17 m When flying from Chicago to New York City, this can take around 2 h and 17 m in flying time, however this flight duration can vary due to other factors. Cheapest flight $9 The best price for flights from Chicago to New York City offered by eDreams, which have been found by our customers in the last 3 days. How long is the flight from Chicago to New York? The flight time from Chicago to New York is 2 hours, 4 minutes. The time spent in the air is 1 hour, 37 minutes. These numbers are averages. In reality, it varies by airline with Spirit being the fastest taking 1 hour, 57 minutes, and Delta the slowest taking 2 hours, 6 minutes. 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 ). 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. Worldwide. $42. Flights to North America, Worldwide. Find flights to Worldwide from $24. Fly from Chicago on Frontier, Spirit Airlines and more. Search for Worldwide flights on KAYAK now to find the best deal. New York John F Kennedy Intl Airport. $251. New York LaGuardia Airport. $259. Newark Airport. Search and compare first class flight deals to New York. Fly from Fort Lauderdale from $639, from Dallas from $709, from Miami from $726. Book your first class tickets to New York. Apr 17, 2024 · Spirit Airlines is one of the most popular airlines used for those traveling from New York to Chicago. Flights on this route from Spirit Airlines typically cost $454.87 RT, a price that is 20% more expensive than the average New York to Chicago flight. The cheapest flight found was $84 RT. 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.Detailed flight information from Chicago ORD to New York JFK. See all airline(s) ... The airlines below are departing from or arriving to other airports in the same city or very close. Southwest Airlines. ... Airlines with direct flights from Chicago to New York in the past. Iberia. Oneworld Last flight was scheduled 2018-05-31 The two airlines most popular with KAYAK users for flights from New York to Chicago are Alaska Airlines and Delta. With an average price for the route of $319 and an overall rating of 8.1, Alaska Airlines is the most popular choice. Delta is also a great choice for the route, with an average price of $276 and an overall rating of 8.0. The two airlines most popular with KAYAK users for flights from New York to Chicago are Alaska Airlines and Delta. With an average price for the route of $319 and an overall rating of 8.1, Alaska Airlines is the most popular choice. Delta is also a great choice for the route, with an average price of $276 and an overall rating of 8.0. 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. Tue, Jun 11 LGA – CLE with Frontier Airlines. Direct. from $39. New York.$40 per passenger.Departing Wed, Jun 5, returning Wed, Jun 12.Round-trip flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departing from Charleston on Wed, Jun 5, arriving in New York Newark.Inbound direct flight with Spirit Airlines departing from ... Flight deals from Chicago O'Hare International to New York Newark. Looking for a cheap last-minute deal or the best round-trip flight from Chicago O'Hare International to New …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 ... Find flights from Chicago to New York (CHI-NYC) with Jetcost. Compare deals from top airlines and travel agencies and find your Chicago - New York flight at the best price. Cheap Flights from Chicago to New York (MDW-NYC) 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. Wed, 12 Jun LGA - ORD with Spirit Airlines. Direct. from $91. New York.$94 per passenger.Departing Tue, 21 May, returning Tue, 4 Jun.Return flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Chicago O'Hare International on Tue, 21 May, arriving in New York LaGuardia.Inbound direct flight with Spirit Airlines ...1 stop. from $132. Las Vegas.$157 per passenger.Departing Tue, Apr 30, returning Tue, May 7.Round-trip flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departing from New York Newark on Tue, Apr 30, arriving in Las Vegas Harry Reid International.Inbound indirect flight with Spirit Airlines, departing from Las Vegas ...The cheapest way to get from Chicago to New York, NY costs only $109, ... Flights from Chicago O'Hare to New York La Guardia Ave. Duration 2h 11m When Every day Estimated price $110 - $ ... The New York City Subway consists of …If you're seeking options on non-stop flights from Chicago to New York, check out these fares. Select from other flights from Chicago to New York by using the search form above. Tue 5/21 11:14 am ORD - LGA. Nonstop 2h 11m Spirit Airlines. Tue 5/21 8:09 pm LGA - ORD. Nonstop 2h 37m Spirit Airlines.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. 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 from New York to Chicago with American Airlines. Round trip. 1 Adult, Economy class. Book with cash. From. To. Depart. 04/30/24. today.From the populous city of Chicago, Illinois, located in the heart of the country, nonstop flights to New York City can take between 2 hours 7 minutes and 2 hours 24 minutes from Chicago O'Hare International Airport (ORD), with flights that stop in Philadelphia taking around 4 hours.Our data shows that the cheapest route for a one-way flight from Chicago O'Hare Intl Airport to New York cost £45 and was between Chicago O'Hare Intl 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 £57.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.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.
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.. Flex securly
Cheap Flights from Chicago (ORD) to New York (JFK) Prices were available within the past 7 days and start at £50 for one-way flights and £101 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. Reserve one-way or return flights from Chicago to New York with no change fee on selected ... Nonstop | Weekend Deal. Chicago, IL (ORD)to Seattle, WA (SEA) Thu, Apr 25 - Sun, Apr 28. Alaska. Find This Deal. See more deals to Seattle, WA (SEA) Load More Flight Deals. Cheap flights from Chicago airport starting at $46 Roundtrip. Compare the best deals and lowest prices to find your next flight from Chicago (ORD) on Airfarewatchdog.This time of year offers the best deals on train tickets from Chicago to New York, with the average price at just $227. Train tickets on this route are most expensive in September, when the average price goes up to $305. You can still score cheap deals below this average price, though, especially if you plan ahead and book your ticket in advance.Atlanta to New York City 26-Jan to 28-Jan $72. San Francisco to New York City 15-Feb to 20-Feb $214. Houston to New York City 27-Feb to 28-Feb $130. Miami, Florida to New York City 5-Mar to 6-Mar $56. Phoenix to New York City 18-Jan to 21-Jan $107. Detroit to New York City 29-Jan to 5-Feb $55.Round-trip. 1 adult. Economy. 0 bags. Direct flights only Add hotel. Sat 5/11. Sat 5/18. Search hundreds of travel sites at once for deals on flights to Chicago O'Hare Airport. …Southwest.com ®; Routes; New York City (LGA) to Chicago (MDW) Flights from New York City (LGA) to Chicago (MDW) If the Second City calls you away from the Big Apple, Southwest Airlines ® has you covered with low fares on nonstop flights. Southwest ® is proud to offer flights from New York (LaGuardia) to Chicago (Midway) at prices that'll …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.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.Use Google Flights to explore cheap flights to anywhere. Search destinations and track prices to find and book your next flight.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.The cheapest flights to John F. Kennedy Intl. found within the past 7 days were $127 round trip and $70 one way. Prices and availability subject to change. Additional terms may apply. Tue, Aug 20 - Tue, Aug 27. ORD. Chicago. JFK. New York. All flight schedules from Chicago Ohare International , Illinois , USA to John F Kennedy International , New York , USA . This route is operated by 3 airline (s), and the flight time is 2 hours and 47 minutes. The distance is 742 miles. Find cheap flights from Chicago to New York. Book the cheapest price and save money with lastminute.com. Call to book. Flight + Hotel. Flash Sales. Holidays. City breaks. Flights. Hotels. ... Cheap flights Mexico City - New York. Departing on Friday, 26 April 2024 and returning on Wednesday, 1 May 2024. from £345 10h ago .Delta Flights From New York to Chicago. Another popular option for New York to Chicago flights is Delta (8.0/10, 11,492 ratings). Delta flies from New York to Chicago around 55 times per week, with deals starting from $84 round-trip and rising to an average price of around $453.Roundtrip. One way. Multi-city. Direct flights only. Origin. Destination. Departure. Return. Passengers. Search Flight + Hotel. Search flights. Last minute flights from Chicago to … 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 ... Direct. from £47. New York. £48 per passenger.Departing Wed, 8 May, returning Wed, 15 May.Return flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Chicago O'Hare International on Wed, 8 May, arriving in New York LaGuardia.Inbound direct flight with Spirit Airlines departs from New York LaGuardia on Wed, 15 ... The cheapest month for flights from New York LaGuardia Airport 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..