$63 Cheap Flights from Chicago (MDW) to New York (LGA)

View $63 flight on Tue, Jan 20, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to LaGuardia Airport (LGA)

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

Prices were available within the past 7 days and start at $63 for one-way flights and $129 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Jan 13 - Wed, Jan 14
MDW
Chicago
LGA
New York
$129 Roundtrip, found 3 days ago
$129
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Jan 13 from Chicago to New York, returning Wed, Jan 14, priced at $129 found 3 days ago
Southwest Airlines
Tue, Oct 7 - Wed, Oct 15
MDW
Chicago
LGA
New York
$132 Roundtrip, found 3 days ago
$132
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Oct 7 from Chicago to New York, returning Wed, Oct 15, priced at $132 found 3 days ago
Southwest Airlines
Mon, Oct 27 - Tue, Oct 28
MDW
Chicago
LGA
New York
$133 Roundtrip, found 3 days ago
$133
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Mon, Oct 27 from Chicago to New York, returning Tue, Oct 28, priced at $133 found 3 days ago
Southwest Airlines
Thu, Jan 8 - Wed, Jan 14
MDW
Chicago
LGA
New York
$134 Roundtrip, found 3 days ago
$134
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Jan 8 from Chicago to New York, returning Wed, Jan 14, priced at $134 found 3 days ago
Southwest Airlines
Tue, Jan 6 - Mon, Jan 12
MDW
Chicago
LGA
New York
$138 Roundtrip, just found
$138
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Jan 6 from Chicago to New York, returning Mon, Jan 12, priced at $138 just found
Southwest Airlines
Wed, Jan 28 - Sat, Jan 31
MDW
Chicago
LGA
New York
$139 Roundtrip, found 4 days ago
$139
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Jan 28 from Chicago to New York, returning Sat, Jan 31, priced at $139 found 4 days ago
Southwest Airlines
Sat, Oct 25 - Tue, Oct 28
MDW
Chicago
LGA
New York
$142 Roundtrip, just found
$142
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, Oct 25 from Chicago to New York, returning Tue, Oct 28, priced at $142 just found
Southwest Airlines
Tue, Dec 16 - Mon, Jan 12
MDW
Chicago
LGA
New York
$143 Roundtrip, found 4 days ago
$143
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Dec 16 from Chicago to New York, returning Mon, Jan 12, priced at $143 found 4 days ago
Frontier Airlines
Fri, Oct 3 - Tue, Oct 7
MDW
Chicago
LGA
New York
$146 Roundtrip, found 4 hours ago
$146
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Fri, Oct 3 from Chicago to New York, returning Tue, Oct 7, priced at $146 found 4 hours ago
Delta
Tue, Dec 16 - Thu, Dec 25
MDW
Chicago
LGA
New York
$283 Roundtrip, found 3 hours ago
$283
Roundtrip
found 3 hours ago
Select Delta flight, departing Tue, Dec 16 from Chicago to New York, returning Thu, Dec 25, priced at $283 found 3 hours ago

Find the cheapest month to fly from Chicago (MDW) to New York (LGA)

February is typically the cheapest month to fly

From $113 - $643 per traveler.

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to LaGuardia Airport (LGA) cost?
Grab a cheap one-way flight from $63 or cheap return flight from $129 from Midway Intl. Airport (MDW) to LaGuardia Airport (LGA) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to LaGuardia Airport (LGA)?
Traveling in January may help you find better deals, as it's the cheapest month for flights between MDW and LGA. You'll often find the lowest prices during off-peak months.
Which airlines fly direct from Midway Intl. Airport (MDW) to LaGuardia Airport (LGA)?
Catch a direct flight with Southwest Airlines and head straight from Midway Intl. Airport (MDW) to LaGuardia Airport (LGA).
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to LaGuardia Airport (LGA)?
Use the filter tool on Expedia to compare different airlines and find the most affordable carrier that'll fly you from MDW to LGA. Then, sort your results by "Price (lowest to highest)" to snag the best deal available.
How many flights per day from Midway Intl. Airport (MDW) to LaGuardia Airport (LGA)?
With an average of 6 direct flights departing from Midway Intl. Airport (MDW) to LaGuardia Airport (LGA) every day, you'll be on your way in no time.
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to LaGuardia Airport (LGA)?
Flights between MDW and LGA are their busiest at 2 PM. If you want a more relaxed atmosphere and potentially cheaper prices, look for a time outside the usual busy windows.
What day of the week has the most flights from MDW to LGA?
Depart on a Friday if you're searching for the biggest selection of flights from Midway Intl. Airport (MDW) to LaGuardia Airport (LGA).
What is the earliest flight from Midway Intl. Airport (MDW) to LaGuardia Airport (LGA)?
The earliest flight jetting off from Midway Intl. Airport (MDW) is at around 6:00AM UTC-6. Catch this flight and you'll land at LaGuardia Airport (LGA) at approximately 9:10AM UTC-5. The total time in the air is 2h 10m.
How long does it take to fly from Midway Intl. Airport (MDW) to LaGuardia Airport (LGA)?
The average flight time from MDW to LGA is 2 hours and 4 minutes, covering a total distance of 720 mi.
What is the best time to fly from Midway Intl. Airport (MDW) to LaGuardia Airport (LGA)?
Opt for a flight from Midway Intl. Airport (MDW) to LaGuardia Airport (LGA) that takes off before 3 PM to reduce the risk of delays and cancellations. Departures after this time are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for New York from Midway Intl. Airport (MDW)?
LaGuardia Airport (LGA) is the only airport in New York with direct flights from Midway Intl. Airport (MDW). Browse your options and discover cheap fares on Expedia.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to LaGuardia Airport (LGA) last-minute?
Waiting until right before your break to book a flight from MDW to LGA often results in higher prices. While you may come across some last-minute offers, there's no guarantee. Keep your travel schedule open for the best chance of scoring a bargain.
Is it cheaper to book a MDW to LGA flight and hotel package?
You can save money by booking a MDW to LGA flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one place. Once you've selected your preferred flights and accommodations, consider other add-ons like car rentals, tours and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to LaGuardia Airport (LGA)?
If you reserved your MDW to LGA flight in the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for further details.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
LaGuardia
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$119
Distance
722 mi
Average flight time
3 hours 7 mins

Book with confidence

Book with confidence

Chicago to New York Flights

The cheapest times to fly from Chicago to New York

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to New York are during the month of January. You can find some of the cheapest flights from Chicago to New York with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to New York

Sunday is one of the best days to book for cheap flights from Chicago to New York: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to New York

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to New York in 2025. You can also book with separate airlines for your outbound and return journeys, from $63 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to New York flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to New York airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to New York Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.