149 € Cheap Flights from New York to Chicago Midway

Compare New York to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from New York to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from New York to Chicago Midway Airport? If you want to travel next month, return fares start from 149 €. Find the lowest prices on one-way and return tickets right here.

Chicago.149 € per passenger.Departing Sat, 26 Sep, returning Sat, 3 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Sat, 26 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 3 Oct, arriving in New York LaGuardia.Price includes taxes and charges.From 149 €, select.

Chicago.149 € per passenger.Departing Wed, 14 Oct, returning Wed, 14 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Wed, 14 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 14 Oct, arriving in New York LaGuardia.Price includes taxes and charges.From 149 €, select.

Chicago.149 € per passenger.Departing Tue, 4 Aug, returning Sat, 15 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Tue, 4 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 15 Aug, arriving in New York LaGuardia.Price includes taxes and charges.From 149 €, select.

Chicago.150 € per passenger.Departing Tue, 21 Jul, returning Tue, 4 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Tue, 21 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 4 Aug, arriving in New York LaGuardia.Price includes taxes and charges.From 150 €, select.

Chicago.150 € per passenger.Departing Wed, 22 Jul, returning Wed, 22 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Wed, 22 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 22 Jul, arriving in New York LaGuardia.Price includes taxes and charges.From 150 €, select.

Chicago.150 € per passenger.Departing Tue, 1 Sep, returning Wed, 2 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Tue, 1 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 2 Sep, arriving in New York LaGuardia.Price includes taxes and charges.From 150 €, select.

Chicago.150 € per passenger.Departing Sat, 29 Aug, returning Tue, 1 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Sat, 29 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 1 Sep, arriving in New York LaGuardia.Price includes taxes and charges.From 150 €, select.

Chicago.167 € per passenger.Departing Wed, 4 Nov, returning Sat, 7 Nov.Return flight with Delta.Outbound indirect flight with Delta, departs from New York Newark on Wed, 4 Nov, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sat, 7 Nov, arriving in New York Newark.Price includes taxes and charges.From 167 €, select.

Chicago.173 € per passenger.Departing Wed, 11 Nov, returning Mon, 16 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Wed, 11 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 16 Nov, arriving in New York LaGuardia.Price includes taxes and charges.From 173 €, select.

Chicago.175 € per passenger.Departing Tue, 1 Sep, returning Sun, 10 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Tue, 1 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 10 Jan, arriving in New York LaGuardia.Price includes taxes and charges.From 175 €, select.

Chicago.181 € per passenger.Departing Tue, 1 Dec, returning Mon, 14 Dec.Return flight with Delta.Outbound indirect flight with Delta, departs from New York Newark on Tue, 1 Dec, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Mon, 14 Dec, arriving in New York Newark.Price includes taxes and charges.From 181 €, select.

Chicago.188 € per passenger.Departing Tue, 27 Oct, returning Mon, 2 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Tue, 27 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 2 Nov, arriving in New York LaGuardia.Price includes taxes and charges.From 188 €, select.

Chicago.198 € per passenger.Departing Tue, 19 Jan, returning Sat, 23 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from New York Newark on Tue, 19 Jan, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sat, 23 Jan, arriving in New York Newark.Price includes taxes and charges.From 198 €, select.

Chicago.198 € per passenger.Departing Sat, 17 Apr, returning Tue, 20 Apr.Return flight with Delta.Outbound indirect flight with Delta, departs from New York Newark on Sat, 17 Apr, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 20 Apr, arriving in New York Newark.Price includes taxes and charges.From 198 €, select.

Chicago.198 € per passenger.Departing Sat, 20 Feb, returning Mon, 22 Feb.Return flight with Delta.Outbound indirect flight with Delta, departs from New York Newark on Sat, 20 Feb, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Mon, 22 Feb, arriving in New York Newark.Price includes taxes and charges.From 198 €, select.

Chicago.198 € per passenger.Departing Wed, 6 Jan, returning Sun, 10 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Wed, 6 Jan, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 10 Jan, arriving in New York LaGuardia.Price includes taxes and charges.From 198 €, select.

Find the cheapest month to fly from New York to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like New York to Chicago Midway flights are currently cheapest in August.

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Direct flights from New York to Chicago Midway

New York to Chicago Midway: Alternative routes

Compare routes from New York to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

New York to Chicago: Flight information

The things to know before you go.

Cheapest flight found	149 €
Cheapest month to fly	August
Average flight time	2 hrs, 38 mins
Most popular airline	Southwest Airlines
Average flights per week	44

Finding cheap flights from New York to Chicago Midway: Frequently asked questions

How much are return flights from New York to Chicago Midway?

The best price we found for a return flight from New York to Chicago Midway is 149 €. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

How long does it take to fly from New York to Chicago Midway?

2 hours and 38 minutes is the average flight time from New York to Chicago Midway.

Which airlines fly direct from New York to Chicago Midway?

Southwest Airlines and United fly direct from New York to Chicago Midway.

How many flights are there a week from New York to Chicago Midway?

As of July 2026, there are 44 flights per week flying from New York to Chicago Midway.

When is the cheapest time to fly from New York to Chicago Midway?

The cheapest month to fly from New York to Chicago Midway is usually August.

Which upcoming date is cheapest to fly from New York to Chicago Midway Airport on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from New York to Chicago Midway Airport on Tuesday, 4 August 2026.

Can I get a direct flight from New York to Chicago Midway Airport?

Yes – the average flight time is 2 hours and 38 minutes.

How can I find the best flight deal to Chicago Midway?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Chicago?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

Which is the cheapest airline to fly from New York to Chicago Midway with?

The cheapest airline that flies to Chicago Midway is Southwest Airlines .

Travelling from New York to Chicago Midway International Airport (MDW): What you need to know

Start planning your trip by checking out where you'll catch your flight from New York to Chicago Midway International Airport (MDW). Explore the options for setting off from Newark Liberty International Airport (EWR) or New York LaGuardia Airport (LGA), the city's main airports.
Chicago Midway International Airport is located in Chicago. The city operates on the UTC-6 timezone and is one hour behind New York.
Arrive at the airport on time so you don't miss your flight from New York to MDW. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid the mad dash to your gate.
With more travellers during peak months like July, get to the terminal earlier than usual. Two hours for domestic flights and as much as four for international journeys will help you deal with longer queues. Remember things also get busy during major holidays like July Fourth.

Airports in New York

New York John F. Kennedy International Airport (JFK)

Located around 24 kilometres from the centre of New York, JFK can be reached in about 45 minutes by car (depending on traffic). The journey by public transport will take roughly 50 minutes.
Booked an early flight from New York to Chicago Midway International Airport? Avoid the mad dash to the terminal (and enjoy a little extra shut-eye) by picking one of these hotels near New York John F. Kennedy International Airport:
Of all flights leaving New York John F. Kennedy International Airport, 73% touch down on time at their destination.
You'll find JFK at JFK Airport.

Newark Liberty International Airport (EWR)

Consider beginning your travels from Newark Liberty International Airport (EWR). You can book a direct New York to Chicago Midway International Airport (MDW) plane ticket from this popular hub.
Board your direct flight from New York to MDW with Frontier Airlines. This is one of the top carriers that operates this route out of EWR.
Frontier Airlines is the most popular choice for passengers flying from EWR to MDW.
Frontier Airlines is rated the most punctual carrier operating flights between Newark Liberty International Airport and Chicago Midway International Airport.
EWR is around 24 kilometres from central New York. It takes 35 minutes or so to get to the airport if you're driving from the city centre. Public transport takes approximately 1 hour.
Get your holiday started early with an extra night away from home. Before catching your New York to MDW flight, unwind in one of these hotels close to Newark Liberty International Airport:
Newark Liberty International Airport has an on-time performance of 71%. This figure reflects how often flights that depart from this airport land on schedule.
You'll find EWR at Building 1, Conrad Road.

New York LaGuardia Airport (LGA)

Board once and be on your way from New York LaGuardia Airport (LGA). Direct flights from New York to Chicago Midway International Airport are available from here.
Get ready to jet away with Southwest Airlines. It offers direct New York to MDW plane tickets from LGA.
The preferred airline for passengers flying between LGA and MDW is Southwest Airlines.
The top on-time carrier on this route is Southwest Airlines. Its services land as planned 65.72% of the time.
From central New York, LGA is around 13 kilometres away. It takes roughly 30 minutes to arrive by car and 55 minutes or so if you're on public transport.
Take the uncertainty out of departure day — stay close to New York LaGuardia Airport and know you'll reach your gate with time to spare. Settle in at one of these hotels the day before if you've booked an early New York to Chicago Midway International Airport flight:
The on-time performance rating of LGA is 69%. To put it simply, that's how frequently flights from this airport arrive as planned.
The address of New York LaGuardia Airport is Hangar 7 Centre.

About Chicago Midway International Airport (MDW)

Have a late flight from New York to Chicago Midway International Airport? Don't let it leave you bleary-eyed. Stay at one of these hotels near MDW and shut your eyes sooner:
Lock in the best possible rate by booking your vehicle around four weeks ahead of your New York to Chicago Midway International Airport flight.
The address for MDW is 5700 South Cicero.

Getting from Chicago Midway International Airport (MDW) to central Chicago

From Chicago Midway International Airport, central Chicago is around 16 kilometres away. It takes about 25 minutes to reach the city centre by car.
Travelling on public transport will take you roughly 30 minutes.

How to find the cheapest flights from New York to Chicago Midway International Airport (MDW)

Right now, 75 € is the lowest price we've found for a one-way ticket from New York to Chicago Midway International Airport. The cheapest price for a return flight is 149 €. Remember fares can change due to demand at the time of booking.
To find cheap flights from New York to MDW, book early. Airlines usually offer their most competitively priced fares when tickets first go on sale.
The 'Whole month' tool will show you the cheapest New York to Chicago Midway International Airport tickets across every month. It's a good way to find a bargain if your dates aren't set in stone.
Finding a cheap plane ticket from New York to MDW couldn't be easier with Price Alerts. All you need to do is set up one of these automatic alerts and we'll get in touch when there's a better deal.
Tailor your travel plans using filters. Choose your ideal arrival and departure times, airlines and total journey duration. You can also sort your results by 'Fastest,' 'Cheapest' or 'Best' flights from New York to Chicago Midway International Airport.

The best time to fly from New York to Chicago Midway International Airport (MDW)

Picture the kind of break you want when deciding the best time to fly. November is the quietest month to visit Chicago. July is when most people book flights from New York to Chicago Midway International Airport (MDW), which may be perfect if you enjoy travelling when it's busier.
The warmest month in Chicago is July, with temperatures ranging between 16ºC (61ºF) and 28ºC (82ºF). Lock in your New York to MDW plane ticket then if that's your ideal forecast.
For cooler conditions, search for a cheap ticket from New York to Chicago Midway International Airport in January when temperatures are between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

Once you've booked your flight from New York to Chicago Midway International Airport, find a hotel that offers the right mix of comfort and location. Make one of these accommodation options your base for exploring Chicago:
Your visit to Chicago isn't complete without checking out the sights. Big-name attractions that should be on your list include Millennium Park, Art Institute of Chicago and Willis Tower.

Explore more of the United States

Indianapolis is just one of the many places in the United States waiting to be discovered once you've seen the sights of Chicago. Around 257 kilometres away to the southeast, top sights here include Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.
Milwaukee is another well-known destination in the United States and is around 137 kilometres north of Chicago. No trip is complete without dropping by Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo.