$217 Cheap Flights from New York to Chicago Midway in 2025

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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? Find the lowest prices on one-way and return tickets right here.

Chicago.$217 per passenger.Departing Tue, 27 May, returning Tue, 27 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Tue, 27 May, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 27 May, arriving in New York LaGuardia.Price includes taxes and charges.From $217, select.

Chicago.$249 per passenger.Departing Wed, 28 May, returning Wed, 25 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Wed, 28 May, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 25 Jun, arriving in New York LaGuardia.Price includes taxes and charges.From $249, select.

Chicago.$274 per passenger.Departing Mon, 19 May, returning Thu, 17 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Mon, 19 May, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 17 Jul, arriving in New York LaGuardia.Price includes taxes and charges.From $274, select.

Chicago.$275 per passenger.Departing Wed, 30 Apr, returning Tue, 6 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Wed, 30 Apr, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 6 May, arriving in New York LaGuardia.Price includes taxes and charges.From $275, select.

Chicago.$281 per passenger.Departing Tue, 5 Aug, returning Thu, 7 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Tue, 5 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 7 Aug, arriving in New York LaGuardia.Price includes taxes and charges.From $281, select.

Chicago.$281 per passenger.Departing Wed, 30 Jul, returning Tue, 5 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Wed, 30 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 5 Aug, arriving in New York LaGuardia.Price includes taxes and charges.From $281, select.

Chicago.$281 per passenger.Departing Tue, 29 Apr, returning Tue, 29 Apr.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Tue, 29 Apr, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 29 Apr, arriving in New York LaGuardia.Price includes taxes and charges.From $281, select.

Chicago.$281 per passenger.Departing Sat, 7 Jun, returning Tue, 10 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Sat, 7 Jun, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 10 Jun, arriving in New York LaGuardia.Price includes taxes and charges.From $281, 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 May.

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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	$217
Cheapest month to fly	May
Average flight time	2 hrs, 27 mins
Most popular airline	Southwest Airlines
Average flights per week	51

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 $217. 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 27 minutes is the average flight time from New York to Chicago Midway.

Which airlines fly direct from New York to Chicago Midway?

Southwest Airlines flies direct from New York to Chicago Midway.

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

As of April 2025, there are 51 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 April 2025.

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, 27 May 2025.

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

Yes – the average flight time is 2 hours and 27 minutes.

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

All great adventures start at one of New York's main airports, Newark Liberty International Airport (EWR) or John F. Kennedy International Airport (JFK). Explore your options for booking a flight from New York to Chicago Midway International Airport (MDW) departing from either of these.
Chicago Midway International Airport is located in Chicago. The city operates in the UTC-5 timezone and is 1 hour behind New York.
The busiest route is from Newark Liberty International Airport (EWR) to Chicago Midway International Airport (MDW), with 35 direct weekly services. If you'd like to get going as soon as possible, the earliest flight from EWR to MDW is the 06:00 Southwest Airlines service. If you prefer travelling later, the last departure is at 21:55 with Southwest Airlines.
To ensure you get on your flight from New York to MDW, allow plenty of time for things like baggage drop and finding your gate. Arriving two hours ahead of international departures and one hour before domestic flights is the standard rule.
Popular months like August or holiday periods such as Christmas and New Year will mean longer waits at check-in and security. If you're travelling then, play it safe and get to the airport even earlier. Arriving two hours before a domestic flight and up four hours ahead of international flights is wise.

Airports in New York

Newark Liberty International Airport (EWR)

From central New York, EWR is approximately 24 kilometres away. Use navigation apps or visit the official airport website to work out the best way to get there.
After a relaxed start to your travels? Stay near Newark Liberty International Airport. Whether you're taking an early flight from New York to Chicago Midway International Airport or want to avoid feeling rushed, these hotels are the answer:

John F. Kennedy International Airport (JFK)

Want more options for a direct flight from New York to Chicago Midway International Airport (MDW)? Browse the fares flying out of John F. Kennedy International Airport (JFK).
JFK is around 48 kilometres from central New York. It'll take 48 minutes or so to get to the airport by car from the city centre. Public transport takes roughly 1 hour and 20 minutes.
Get your holiday started early with an extra night away from home. Before catching your flight from New York to MDW, stay in one of these hotels near John F. Kennedy International Airport:

About Chicago Midway International Airport (MDW)

Book a hotel close to MDW if you're taking a late flight from New York to Chicago Midway International Airport. Select one of these accommodation options and avoid the hassle of a long transfer:

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

Chicago Midway International Airport is approximately 19 kilometres from central Chicago. With your own car rental or if you're catching a cab, the drive is around 21 minutes.
Getting there by public transport takes around 46 minutes.

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

$109 is the cheapest price we've found for a one-way ticket from New York to Chicago Midway International Airport. Return flights start from $217. Prices are subject to change based on availability and may vary at the time of booking.
Don't leave things to the last moment. You're more likely to get flight tickets from New York to MDW if you book ahead. Airlines often have some amazing early bird rates.
If you're flexible with your trip dates, check out the 'Whole month' tool. It'll give you the cheapest price across the month when searching for your ticket from New York to Chicago Midway International Airport.
Create a Price Alert for flight tickets from New York to MDW. There's no need to check back in every day to see whether fares have dropped. We'll notify you as soon as the price changes.
Personalise your trip by applying filters. Adjust the duration, number of stops, and arrival and departure times to find the ideal flight from New York to Chicago Midway International Airport. You can also sort the results to see the 'Best,' 'Fastest' or 'Cheapest' options first.

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

It's time to work out your trip dates for your flight from New York to Chicago Midway International Airport. July is the busiest month for a trip to Chicago. If you prefer a more relaxed atmosphere, go in May.
Before you book a flight from New York to MDW, think about the kind of weather you enjoy. July is the warmest month in Chicago, with the temperature ranging from 15ºC to 29ºC.
Look for cheap flights from New York to Chicago Midway International Airport in January if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC and 3ºC on average.

More about Chicago

Start your Chicago trip right by choosing the perfect place to stay. As soon as you've booked your flight from New York to Chicago Midway International Airport, browse our selection of accommodation options including:
Millennium Park and Art Institute of Chicago are just two of the top-rated attractions to put on your Chicago to-do list. Keep the adventure rolling by checking out LandShark Beer Garden at Navy Pier.

Complete your Chicago trip with a car rental

Shut down all those tabs and let us do the hard work for you. We've also got incredible deals on car rentals in Chicago once you've booked your hotel and cheap flight from New York to Chicago Midway International Airport. Easily compare prices all in one place and drive away with the lowest rate in town.