Cheap Flights from New York LaGuardia to Chicago Midway

Compare New York LaGuardia to Chicago Midway flight deals

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

Book the best Chicago Midway fare with no extra fees

Flight deals from New York LaGuardia to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from New York LaGuardia to Chicago Midway? Find the lowest prices on one-way and return tickets right here.

Chicago.R 1,099 per passenger.Departing Sat, 17 Jan.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from New York LaGuardia on Sat, 17 Jan, arriving in Chicago Midway.Price includes taxes and charges.From R 1,099, select.

Chicago.R 1,101 per passenger.Departing Sat, 13 Dec.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from New York LaGuardia on Sat, 13 Dec, arriving in Chicago Midway.Price includes taxes and charges.From R 1,101, select.

Chicago.R 1,109 per passenger.Departing Sat, 21 Feb.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from New York LaGuardia on Sat, 21 Feb, arriving in Chicago Midway.Price includes taxes and charges.From R 1,109, select.

Chicago.R 1,185 per passenger.Departing Mon, 23 Feb.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Mon, 23 Feb, arriving in Chicago Midway.Price includes taxes and charges.From R 1,185, select.

Chicago.R 1,189 per passenger.Departing Sat, 13 Dec.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Sat, 13 Dec, arriving in Chicago Midway.Price includes taxes and charges.From R 1,189, select.

Chicago.R 1,189 per passenger.Departing Sun, 18 Jan.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Sun, 18 Jan, arriving in Chicago Midway.Price includes taxes and charges.From R 1,189, select.

Chicago.R 1,204 per passenger.Departing Mon, 2 Mar.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Mon, 2 Mar, arriving in Chicago Midway.Price includes taxes and charges.From R 1,204, select.

Chicago.R 1,611 per passenger.Departing Sat, 30 May.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Sat, 30 May, arriving in Chicago Midway.Price includes taxes and charges.From R 1,611, select.

Find the cheapest month to fly from New York LaGuardia 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 LaGuardia to Chicago Midway flights are currently cheapest in January.

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Direct flights from New York LaGuardia to Chicago Midway

New York LaGuardia to Chicago Midway: Alternative routes

Compare routes from New York LaGuardia 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	R 1,099
Cheapest month to fly	January
Average flight time	2 hrs, 33 mins
Most popular airline	Southwest Airlines
Average flights per week	54

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

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

The best price we found for a return flight from New York LaGuardia to Chicago Midway is R 2,186. 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 LaGuardia to Chicago Midway?

2 hours and 33 minutes is the average flight time from New York LaGuardia to Chicago Midway.

Which airlines fly direct from New York LaGuardia to Chicago Midway?

Southwest Airlines flies direct from New York LaGuardia to Chicago Midway.

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

As of November 2025, there are 54 flights per week flying from New York LaGuardia to Chicago Midway.

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

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

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

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from New York LaGuardia Airport to Chicago Midway Airport on Wednesday, 7 January 2026.

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

Yes – the average flight time is 2 hours and 33 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 LaGuardia Airport to Chicago Midway with?

Currently, Frontier Airlines and Southwest Airlines offer the cheapest flight tickets to Chicago Midway.

Travelling from LaGuardia Airport (LGA) to Chicago Midway International Airport (MDW): what you need to know

Around 2 hours 30 minutes is how long you can expect to be in the air on a direct flight from LaGuardia Airport to Chicago Midway International Airport.
Chicago is one hour behind New York and is in the UTC-5 timezone.
Flights from LGA to MDW start from 06:00 — the first with Southwest Airlines. The latest departure is at 21:55 with Southwest Airlines. Overall, you can choose from 35 weekly LaGuardia Airport to Chicago Midway International Airport flights.
Arrive at the airport on time so you don't miss your LGA to MDW flight. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid sprinting to your gate.
Be prepared for longer queues in popular months like July. Arriving up to four hours ahead of an international flight and two hours for a domestic departure is a wise move.
Southwest Airlines offers direct flights from LaGuardia Airport to Chicago Midway International Airport. Book with this popular airline, then get ready to discover the sights in Chicago — and maybe even more of United States if you have time.
The airline with the highest passenger demand on this route is Southwest Airlines.
With 75.91% of its services arriving as planned, Southwest Airlines is the most punctual carrier operating LGA to MDW flights.
We make it simple to book a flight with a stopover. To see your options for tickets from LaGuardia Airport to Chicago Midway International Airport, uncheck 'Direct flights only.' Then, pick a flight offering a stop long enough to explore your chosen city. Popular stopovers between LGA and MDW include:
- Pittsburgh International Airport
- Detroit Metropolitan Wayne County Airport
- Gerald R. Ford International Airport

How to find the cheapest flights from LaGuardia Airport (LGA) to Chicago Midway International Airport (MDW)

R 1,099 is currently the best price for a one-way LaGuardia Airport to Chicago Midway International Airport flight. A return flight starts at R 2,186. These prices can change based on demand and availability.
Get cheap tickets from LGA to MDW by booking at least six months ahead. Based on our research, that's the sweet spot for bagging a bargain.
May is the cheapest month for flights from LaGuardia Airport to Chicago Midway International Airport. If you're looking to fly at a different time of year, the 'Whole month' tool will show you the lowest prices across every month.
Snapping up cheap flights from LGA to MDW couldn't be easier with Price Alerts. All you need to do is create one of these automatic alerts and we'll notify you as soon as a new discounted fare appears.
Choose your ideal arrival and departure times, airlines and number of stops with the filters. Or sort your results by 'Cheapest' to get the best deals on flights from LaGuardia Airport to Chicago Midway International Airport.

Handy information about LaGuardia Airport (LGA)

You'll find LGA at Hangar 7 Centre.
LaGuardia Airport earns top marks for its on-time performance. 80.0% of flights that take off from LGA reach their destination without delay.
To get to LaGuardia Airport from central New York, it takes around 25 minutes if you're going by car. This depends on traffic, however. It's approximately 18 kilometres from the airport to the city centre.
The journey on public transport takes about 1 hour.
Catching an early flight from LaGuardia Airport to Chicago Midway International Airport? Avoid the stress of rushing to the airport (and catch some extra z's) by picking one of these hotels close to LGA:

Arriving at Chicago Midway International Airport (MDW)

Book a hotel close to MDW if you're catching a late LaGuardia Airport to Chicago Midway International Airport flight. Check in to one of these accommodation options and avoid the hassle of a long transfer:
Pick up a Chicago Midway International Airport rental car and discover Chicago and beyond with your own wheels. Dollar, Hertz and Budget are popular providers to choose from here.
To secure the lowest price, book your ride from Chicago Midway International Airport about four weeks ahead.

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

MDW is located at 5700 South Cicero.
From Chicago Midway International Airport, Chicago is approximately 19 kilometres away. It takes around 20 minutes to drive to the centre.
It takes roughly 45 minutes to get there using public transport.

When to fly to Chicago Midway International Airport (MDW)

July is the most popular month for flights from LaGuardia Airport to Chicago Midway International Airport. To skip the crowds, go to Chicago in May.
Book your flight from LaGuardia Airport to Chicago Midway International Airport for July if you want to go to Chicago during its warmest month. You can expect temperatures of between 15ºC (59ºF) and 29ºC (84ºF).
January has average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Search for cheap tickets from LGA to MDW sometime then if you want to travel in cooler conditions.

Explore more of United States

Columbus is just one of the many cities in United States waiting to be explored after you've experienced Chicago. Around 451 kilometres away to the south-east, popular attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.
Indianapolis is another sought-after destination in United States and is around 257 kilometres south-east of Chicago. No trip is complete without a visit to The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.