$69 Cheap Flights from New York (LGA) to Chicago (MDW)

View $69 flight on Tue, Sep 2, 2025Opens in a new window

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

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • one key icon

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

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

Prices were available within the past 7 days and start at $69 for one-way flights and $142 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Sep 3 - Tue, Sep 9
LGA
New York
MDW
Chicago
$142 Roundtrip, found 9 hours ago
$142
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Wed, Sep 3 from New York to Chicago, returning Tue, Sep 9, priced at $142 found 9 hours ago
Southwest Airlines
Thu, Aug 21 - Tue, Aug 26
LGA
New York
MDW
Chicago
$147 Roundtrip, found 5 days ago
$147
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Aug 21 from New York to Chicago, returning Tue, Aug 26, priced at $147 found 5 days ago
Southwest Airlines
Tue, Sep 2 - Fri, Sep 5
LGA
New York
MDW
Chicago
$152 Roundtrip, found 17 hours ago
$152
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Tue, Sep 2 from New York to Chicago, returning Fri, Sep 5, priced at $152 found 17 hours ago
Southwest Airlines
Sat, Nov 8 - Sun, Nov 9
LGA
New York
MDW
Chicago
$157 Roundtrip, just found
$157
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, Nov 8 from New York to Chicago, returning Sun, Nov 9, priced at $157 just found
Southwest Airlines
Wed, Aug 27 - Thu, Sep 4
LGA
New York
MDW
Chicago
$162 Roundtrip, found 2 days ago
$162
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Aug 27 from New York to Chicago, returning Thu, Sep 4, priced at $162 found 2 days ago
Southwest Airlines
Wed, Sep 3 - Tue, Sep 9
LGA
New York
MDW
Chicago
$163 Roundtrip, found 9 hours ago
$163
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Wed, Sep 3 from New York to Chicago, returning Tue, Sep 9, priced at $163 found 9 hours ago
Southwest Airlines
Thu, Aug 21 - Tue, Aug 26
LGA
New York
MDW
Chicago
$167 Roundtrip, found 5 days ago
$167
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Aug 21 from New York to Chicago, returning Tue, Aug 26, priced at $167 found 5 days ago
Southwest Airlines
Thu, Sep 18 - Sun, Sep 21
LGA
New York
MDW
Chicago
$167 Roundtrip, just found
$167
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Sep 18 from New York to Chicago, returning Sun, Sep 21, priced at $167 just found
Frontier Airlines
Sat, Sep 6 - Tue, Sep 9
LGA
New York
MDW
Chicago
$208 Roundtrip, just found
$208
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Sep 6 from New York to Chicago, returning Tue, Sep 9, priced at $208 just found
Delta
Tue, Sep 23 - Tue, Oct 7
LGA
New York
MDW
Chicago
$217 Roundtrip, just found
$217
Roundtrip
just found
Select Delta flight, departing Tue, Sep 23 from New York to Chicago, returning Tue, Oct 7, priced at $217 just found

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

March is typically the cheapest month to fly

From $110 - $484 per traveler.

Graph displaying average flight prices per month

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 $176
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $176
Flights from New York (LGA) to Chicago (MDW)
Origin airport
LaGuardia
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$137
Distance
722 mi
Average flight time
1 hour 23 mins

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 September. 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 $69 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.

 

Frequently asked questions

How much does a flight from LaGuardia Airport (LGA) to Midway Intl. Airport (MDW) cost?
You can book cheap return tickets starting from $114 from LaGuardia Airport (LGA) to Midway Intl. Airport (MDW). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines and Spirit Airlines flight leaving LGA on August 19 2025 and touching down at MDW. The price was last updated on July 23 2025 and has not changed since.
What is the cheapest month to fly from LGA to MDW?
The cheapest flights from LGA to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
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 LGA to MDW?
Travel from LGA to MDW with Southwest Airlines. This airline currently offers the cheapest one-way ticket for this route, starting at $69. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from LGA on September 2 2025. Prices were last updated on July 23 2025 and have not changed since.
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.

Explore a world of travel with Expedia

Chicago nearby Airports

Chicago

New York to O'Hare Intl.
$89.98
New York nearby Airports

Newark Liberty Intl. Airport

Westchester County to Chicago
$106.29

New York

John F. Kennedy Intl. to Chicago
$216.73

Islip

MacArthur to Chicago
$227.98

White Plains

Westchester County to Chicago
$296.73
*Available to One Key members.