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Cheap flights from New York LaGuardia to Chicago Midway

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Compare New York LaGuardia 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 LaGuardia to Chicago Midway

Looking for a cheap last-minute deal or the best round-trip flight from New York LaGuardia to Chicago Midway? Find the lowest prices on one-way and round-trip tickets right here.
Chicago.C$154 per passenger.Departing Wed, Apr 2, returning Sat, Apr 5.Round-trip flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departing from New York LaGuardia on Wed, Apr 2, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Sat, Apr 5, arriving in New York LaGuardia.Price includes taxes and charges.From C$154, select.
Chicago.C$177 per passenger.Departing Thu, May 8, returning Wed, May 14.Round-trip flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departing from New York LaGuardia on Thu, May 8, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Wed, May 14, arriving in New York LaGuardia.Price includes taxes and charges.From C$177, select.
Chicago.C$181 per passenger.Departing Wed, Mar 26, returning Wed, Apr 2.Round-trip flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departing from New York LaGuardia on Wed, Mar 26, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Wed, Apr 2, arriving in New York LaGuardia.Price includes taxes and charges.From C$181, select.
Chicago.C$181 per passenger.Departing Mon, Apr 21, returning Tue, May 20.Round-trip flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departing from New York LaGuardia on Mon, Apr 21, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Tue, May 20, arriving in New York LaGuardia.Price includes taxes and charges.From C$181, select.
Chicago.C$200 per passenger.Departing Mon, May 26, returning Tue, May 27.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from New York LaGuardia on Mon, May 26, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Tue, May 27, arriving in New York LaGuardia.Price includes taxes and charges.From C$200, select.
Chicago.C$207 per passenger.Departing Tue, May 27, returning Tue, Jun 3.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from New York LaGuardia on Tue, May 27, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Tue, Jun 3, arriving in New York LaGuardia.Price includes taxes and charges.From C$207, select.
Chicago.C$209 per passenger.Departing Sat, Apr 19, returning Sat, Apr 26.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from New York LaGuardia on Sat, Apr 19, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Sat, Apr 26, arriving in New York LaGuardia.Price includes taxes and charges.From C$209, select.
Chicago.C$216 per passenger.Departing Sat, Mar 22, returning Tue, Mar 25.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from New York LaGuardia on Sat, Mar 22, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Tue, Mar 25, arriving in New York LaGuardia.Price includes taxes and charges.From C$216, 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 April.
Mar
from C$216
Apr
from C$154
May
from C$177
Jun
from C$218
Jul
from C$260
Aug
from C$290
Sep
from C$402
Oct
from C$387
Nov
Find prices
Dec
Find prices
Jan
Find prices
Feb
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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 foundC$154
Cheapest month to flyApril
Average flight time2 hrs, 27 mins
Most popular airlineSouthwest Airlines
Average flights per week49

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

The best price we found for a round-trip flight from New York LaGuardia to Chicago Midway is C$154. 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.
2 hours and 27 minutes is the average flight time from New York LaGuardia to Chicago Midway.
Southwest Airlines flies direct from New York LaGuardia to Chicago Midway.
There are 49 flights per week flying from New York LaGuardia to Chicago Midway, as of March 2025.
The cheapest month to fly from New York LaGuardia to Chicago Midway is usually March 2025.
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, April 2, 2025.
Yes – the average flight time is 2 hours and 27 minutes.
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.
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.
Currently, Frontier Airlines and Southwest Airlines offer the cheapest flight tickets to Chicago Midway.

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

  • A direct flight from LaGuardia Airport to Chicago Midway International Airport takes an average of 2 hours 28 minutes. The timezone in Chicago is UTC-5, making it 1 hour behind New York.

  • There are 35 flights from LaGuardia Airport to Chicago Midway International Airport each week. Jump on the 05:10 flight if you want to leave as early as possible. If you're keen to make the most of your day before leaving, the last flight from LGA to MDW departs at 21:55.

  • If you're jetting off during a major holiday or other peak period, allow extra time. A good general rule is two hours ahead of domestic flights and up to four hours before international departures. Lines at security and check-in will be longer.

  • We make it a cinch to book a flight with a stopover. To see all the options for flights from LaGuardia Airport to Chicago Midway International Airport, deselect 'Direct flights only.' Then, pick a flight offering a stop long enough to explore your chosen city. Some popular stopovers between LGA and MDW include:

    • Detroit Metropolitan Wayne County Airport

    • Gerald R. Ford International Airport

    • Pittsburgh International Airport

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

  • The lowest price we've found for a one-way ticket from LaGuardia Airport to Chicago Midway International Airport is C$77. For a return flight on this route, the best price is C$154. Depending on the availability and when you book, these fares can change.

  • Book 9 months before you travel. After crunching the numbers on our calendar, this is how far you should book ahead to find cheap flight tickets from LGA to MDW.

  • The cheapest month for flight tickets from LaGuardia Airport to Chicago Midway International Airport is May. Use the 'Whole month' tool to see the lowest prices if you have flexible dates.

  • Sign into your online account or use the app to create a Price Alert. You'll be notified right away if there's a cheaper deal on this route. It's simple to do, and it'll save you time searching for cheap flight tickets from LGA to MDW every day.

  • Tailor your flights with filters. Pick your departure and arrival times, total journey duration and airlines. You can also sort the results by 'Best,' 'Fastest' or 'Cheapest' flights from LaGuardia Airport to Chicago Midway International Airport.

Handy information about LaGuardia Airport (LGA)

  • Traveling from central New York to LaGuardia Airport takes about 58 minutes on public transport. If you ride-share, drive or grab a cab, you'll cover the 18 kilometres in 27 minutes or so, depending on traffic.

  • Taking an early flight from LaGuardia Airport to Chicago Midway International Airport? Avoid rushing to the airport (and get some extra shut-eye) by picking one of these stays near LGA:

Arriving at Chicago Midway International Airport (MDW)

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

  • From Chicago Midway International Airport, Chicago is approximately 19 kilometres away. It takes around 21 minutes to reach the center driving.

  • If you're taking public transport, expect a journey time of roughly 46 minutes.

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, visit Chicago in May.

  • Lock in your flight from LaGuardia Airport to Chicago Midway International Airport for July if you want to explore Chicago during its warmest month. You can expect temperatures of between 15ºC and 29ºC.

  • January has average temperatures of between -12ºC and 3ºC. Search for cheap flight tickets from LGA to MDW sometime around then if you like traveling in cooler conditions.

More about Chicago

Complete your Chicago trip with hotels and a car rental

  • Comparing flights is not the only thing we're good at. Once you've secured your cheap ticket to Chicago Midway International Airport, check out our car rental offers that'll give you the flexibility to travel around at your own pace. Then, have a look at our exclusive rates for hotels to find your perfect Chicago stay.

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Plan the rest of your trip from New York to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.