$55 Cheap Flights from New York (LGA) to Chicago (MDW)

View $55 flight on Thu, Nov 13, 2025Opens in a new window

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

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Today's featured flight deals from LaGuardia Airport (LGA) to Chicago Midway Airport (MDW)

Nonstop
Carry-on included
Lower price than typical

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

Prices were available within the past 7 days and start at $55 for one-way flights and $110 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Thu, Nov 13 - Sat, Nov 15
LGA
New York
MDW
Chicago
$110 Roundtrip, found 17 hours ago
$110
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Thu, Nov 13 from New York to Chicago, returning Sat, Nov 15, priced at $110 found 17 hours ago
Frontier Airlines
Fri, Dec 5 - Mon, Dec 8
LGA
New York
MDW
Chicago
$127 Roundtrip, found 3 hours ago
$127
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Fri, Dec 5 from New York to Chicago, returning Mon, Dec 8, priced at $127 found 3 hours ago
Southwest Airlines
Fri, Dec 5 - Mon, Dec 8
LGA
New York
MDW
Chicago
$130 Roundtrip, found 3 hours ago
$130
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Fri, Dec 5 from New York to Chicago, returning Mon, Dec 8, priced at $130 found 3 hours ago
Frontier Airlines
Sat, Dec 13 - Tue, Dec 16
LGA
New York
MDW
Chicago
$130 Roundtrip, found 2 days ago
$130
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Dec 13 from New York to Chicago, returning Tue, Dec 16, priced at $130 found 2 days ago
Southwest Airlines
Wed, Dec 3 - Mon, Dec 8
LGA
New York
MDW
Chicago
$134 Roundtrip, found 23 hours ago
$134
Roundtrip
found 23 hours ago
Select Southwest Airlines flight, departing Wed, Dec 3 from New York to Chicago, returning Mon, Dec 8, priced at $134 found 23 hours ago
Frontier Airlines
Fri, Dec 12 - Tue, Dec 16
LGA
New York
MDW
Chicago
$134 Roundtrip, found 18 hours ago
$134
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Fri, Dec 12 from New York to Chicago, returning Tue, Dec 16, priced at $134 found 18 hours ago
Frontier Airlines
Thu, Dec 4 - Sun, Dec 7
LGA
New York
MDW
Chicago
$136 Roundtrip, found 22 hours ago
$136
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Thu, Dec 4 from New York to Chicago, returning Sun, Dec 7, priced at $136 found 22 hours ago
Southwest Airlines
Wed, Dec 10 - Mon, Dec 15
LGA
New York
MDW
Chicago
$137 Roundtrip, just found
$137
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, Dec 10 from New York to Chicago, returning Mon, Dec 15, priced at $137 just found
Southwest Airlines
Thu, Jan 22 - Mon, Jan 26
LGA
New York
MDW
Chicago
$139 Roundtrip, found 1 hour ago
$139
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Thu, Jan 22 from New York to Chicago, returning Mon, Jan 26, priced at $139 found 1 hour ago
Delta
Tue, Feb 3 - Tue, Feb 24
LGA
New York
MDW
Chicago
$283 Roundtrip, found 19 hours ago
$283
Roundtrip
found 19 hours ago
Select Delta flight, departing Tue, Feb 3 from New York to Chicago, returning Tue, Feb 24, priced at $283 found 19 hours ago

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

March is typically the cheapest month to fly

From $110 - $482 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $77
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $77

Frequently asked questions

How much does a flight from LaGuardia Airport (LGA) to Midway Intl. Airport (MDW) cost?
Secure a cheap one-way flight from $55 or cheap return flight from $110 from LaGuardia Airport (LGA) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from LaGuardia Airport (LGA) to Midway Intl. Airport (MDW)?
November is the least expensive month to fly from LGA to MDW. Timing your trip outside of the busy season is often the key to finding better fares.
Which airlines fly direct from LaGuardia Airport (LGA) to Midway Intl. Airport (MDW)?
Catch a direct flight with Southwest Airlines and head straight from LaGuardia Airport (LGA) to Midway Intl. Airport (MDW).
What is the cheapest airline that flies from LaGuardia Airport (LGA) to Midway Intl. Airport (MDW)?
To find the cheapest airline that'll fly you from LGA to MDW, use Expedia's filter tool. Tailor your search based on what matters most to you, such as preferred carriers and ideal departure window. You can then sort your results by "Price (lowest to highest)" to see the cheapest fares upfront.
How many flights per day from LaGuardia Airport (LGA) to Midway Intl. Airport (MDW)?
When departing from LaGuardia Airport (LGA), you can choose from an average of 6 daily direct flights to Midway Intl. Airport (MDW).
What are the most popular departure times for flights from LaGuardia Airport (LGA) to Midway Intl. Airport (MDW)?
More passengers fly between LGA and MDW at 2 PM than at any other time. Prefer a quieter experience? Travel outside of rush hours and you're likely to save on your ticket as well.
What day of the week has the most flights from LGA to MDW?
Friday has the most flights from LaGuardia Airport (LGA) to Midway Intl. Airport (MDW). Consider traveling on this day and you'll have a greater chance of finding a departure that fits your itinerary.
What is the earliest flight from LaGuardia Airport (LGA) to Midway Intl. Airport (MDW)?
LaGuardia Airport (LGA)'s earliest flight to Midway Intl. Airport (MDW) leaves at approximately 6:00AM UTC-5. With a travel duration of 2h 35m, you'll arrive at around 7:35AM UTC-6.
How long does it take to fly from LaGuardia Airport (LGA) to Midway Intl. Airport (MDW)?
The average flight time from LGA to MDW is 2 hours and 35 minutes, covering a total distance of 720 mi.
What is the best time to fly from LaGuardia Airport (LGA) to Midway Intl. Airport (MDW)?
Opt for a flight from LaGuardia Airport (LGA) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the risk of cancellations and delays. Departures later than this have a 22% higher chance of being canceled, on average.**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 Chicago from LaGuardia Airport (LGA)?
You'll land at O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW) when you travel to Chicago on a direct flight from LaGuardia Airport (LGA).
Is it cheaper to buy a plane ticket from LaGuardia Airport (LGA) to Midway Intl. Airport (MDW) last-minute?
Waiting until just before your departure to book a flight from LGA to MDW often results in higher prices. While you might find some last-minute discounts, they aren't always guaranteed. Be flexible with your travel plans for the best chance of landing a bargain.
Is it cheaper to book a LGA to MDW flight and hotel package?
Compared with arranging flights and hotels separately, booking a LGA to MDW flight and hotel package with Expedia could result in significant savings. Better yet, having everything in one place will take the hassle out of planning your trip. Just pick your flights and select from our extensive range of hotels, then tailor your trip with extras like tours and car rentals.
Can I cancel or change the date of my flight from LaGuardia Airport (LGA) to Midway Intl. Airport (MDW)?
If you reserved your LGA to MDW flight in the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of fare you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for more information.

Travel information

Origin airport
LaGuardia
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$110
Distance
722 mi
Average flight time
1 hour 26 mins

Book with confidence

New York to Chicago Flights

The cheapest times to fly from New York to Chicago

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 New York to Chicago are during the month of November. You can find some of the cheapest flights from New York to Chicago with Expedia's search tool and vast selection of airlines.

 

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

Sunday is one of the best days to book for cheap flights from New York to Chicago: 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 New York to Chicago

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 New York to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $55 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 New York to Chicago 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 New York to Chicago 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.

 

New York to Chicago Flights

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*Available to One Key members.