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Cheap Flights from New York to Chicago (LGA to MDW)

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New York to Chicago

Flight Information from New York to Chicago

Cheapest month to fly

December

When is the cheapest flight time from New York to Chicago?

Origin	Destination	Departure Date	Price
New York (NEWA)	Chicago (MDW)	Monday, 1 September 2025	No data
New York (NEWA)	Chicago (MDW)	Saturday, 11 October 2025	S$132
New York (NEWA)	Chicago (MDW)	Saturday, 1 November 2025	No data
New York (NEWA)	Chicago (MDW)	Thursday, 4 December 2025	S$90
New York (NEWA)	Chicago (MDW)	Thursday, 1 January 2026	No data
New York (NEWA)	Chicago (MDW)	Sunday, 1 February 2026	No data
New York (NEWA)	Chicago (MDW)	Sunday, 1 March 2026	No data
New York (NEWA)	Chicago (MDW)	Wednesday, 1 April 2026	No data
New York (NEWA)	Chicago (MDW)	Tuesday, 19 May 2026	S$142
New York (NEWA)	Chicago (MDW)	Monday, 1 June 2026	No data
New York (NEWA)	Chicago (MDW)	Wednesday, 1 July 2026	No data
New York (NEWA)	Chicago (MDW)	Saturday, 1 August 2026	No data

Flight Schedule from New York to Chicago

The following are all scheduled flights from New York to Chicago, with the shortest duration being 0 hours and 0 minutes.

Fri, 19 Sept 2025 (Today)

Sat, 20 Sept 2025

Sun, 21 Sept 2025

Airline	Departure Time	Arrival Time	Origin airport	Destination airport
Southwest Airlines	09:10	10:35	New York (LGA)	Chicago (MDW)	Book flight
Southwest Airlines	11:00	12:25	New York (LGA)	Chicago (MDW)	Book flight
Southwest Airlines	14:00	15:25	New York (LGA)	Chicago (MDW)	Book flight
Southwest Airlines	15:40	17:10	New York (LGA)	Chicago (MDW)	Book flight
Southwest Airlines	18:15	19:35	New York (LGA)	Chicago (MDW)	Book flight
Southwest Airlines	21:40	23:00	New York (LGA)	Chicago (MDW)	Book flight

Direct flight from New York to Chicago

Non-stop airline flights between New York and Chicago

Airticket booking for direct flights from New York to Chicago is now easier than ever. Travel in just 0 hours and 0 minutes, with fares starting at each way.

Southwest Airlines

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About Chicago

Looking for cheap flights from New York to Chicago? Discover the best deals for flight tickets on Traveloka! Flying from New York to Chicago will be more enjoyable with our exclusive Traveloka flight promo. Not just flights, you can also find discounted hotels, airport transfers, and attraction tickets from all over the world. With our complete product offering, booking one-way, round-trip, and multi-city flights will be much easier. Book now and dive into endless adventures with Traveloka!

Flight Information to Chicago

Flight Duration	0 hr(s) 0 mins
Airport in New York	La Guardia (LGA)
Airport in Chicago	Chicago Midway International Airport (MDW)

Frequently Asked Questions

How much is a flight ticket from New York to Chicago?

Planning to take off from New York to Chicago? Grab your ticket on Traveloka with prices starting from , along with additional discounts & promos that can be found on our promo page.

How early should I get to the airport for a domestic & international flight?

For domestic flights, we recommend arriving at the airport at least 2 hours before your scheduled departure time. For international flights, aim to be at the airport at least 3 hours prior to ensure smooth check-in, security checks, and to account for any unexpected delays. It’s better to be early and relaxed than rushing at the last minute right?

When is the best time to buy airline tickets?

Timing is everything when it comes to grabbing airline tickets. Typically, it’s best to book around 4-6 weeks in advance for domestic flights and 2-3 months for international routes. But the prices also depend on the travel demand, seasonality, and major events. You can always monitor the fare trends on Traveloka and set alerts to catch the best deals or promotions!

What is the cheapest day to fly to Chicago?

Looking for the best deals to Chicago? Historically, midweek flights (particularly on Tuesdays and Wednesdays), tend to be cheaper due to lower demand. However, airfares can fluctuate so we recommend keeping an eye on flight prices and being flexible with your travel dates. Booking in advance can be one the hacks to travel to Chicago without breaking the bank!

What information do I need to know when booking a flight?

When booking a flight, every choice sets the tone for your trip. From the preferred flight route – be it direct or with layovers – to the in-flight experience – whether you opt for a standard economy seat or a luxurious first-class journey – and understanding baggage limits, there's a lot to weigh. Other considerations include travel insurance and the airline's booking policies.

How far in advance should I book an international flight?

For international flights, it’s wise to start your search about 5-6 months ahead with the optimal booking window being around 3-4 months before departure. This period often provides a balance between good fares and a reasonable choice of flight times and routes. But please note that several factors such as destination popularity, peak travel season, and regional major events can influence the timeline.

Do I need a passport and visa to fly between New York to Chicago?

Traveling from New York to Chicago typically requires specific documents. For international flights, a passport is almost always necessary. However, for domestic flights, neither a passport nor a visa is usually required, but an official ID will be needed. The necessity of a visa depends on the traveler's citizenship and Chicago's entry regulations. It's crucial to verify visa requirements, as rules can differ between countries.

Why should I book my flight with Traveloka?

Booking flight tickets with Traveloka can feel like diving into an ocean of options! Our platform provides the most comprehensive choices to ensure you find the perfect flight for your adventure. With our smooth booking process, you'll also be provided with a variety of payment methods. Anxious about transacting online? We've got you covered with our top-tier security for each transaction! With Traveloka, your flight booking journey becomes hassle-free!

Is there any available promo in Traveloka?

Yes, you can save 5% off on Flights, Hotels, and Attractions up to S$100 using BOOKTRAVELOKA promo code if you are a new user. The promo is only valid for bookings made through the Traveloka App only.