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

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

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

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

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 - Sat, Sep 6
MDW
Chicago
LGA
New York
$142 Roundtrip, found 7 hours ago
$142
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Wed, Sep 3 from Chicago to New York, returning Sat, Sep 6, priced at $142 found 7 hours ago
Southwest Airlines
Tue, Sep 23 - Wed, Sep 24
MDW
Chicago
LGA
New York
$147 Roundtrip, found 2 hours ago
$147
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Tue, Sep 23 from Chicago to New York, returning Wed, Sep 24, priced at $147 found 2 hours ago
Southwest Airlines
Sat, Aug 30 - Sun, Aug 31
MDW
Chicago
LGA
New York
$152 Roundtrip, just found
$152
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, Aug 30 from Chicago to New York, returning Sun, Aug 31, priced at $152 just found
Southwest Airlines
Tue, Sep 2 - Fri, Sep 5
MDW
Chicago
LGA
New York
$153 Roundtrip, found 1 hour ago
$153
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Tue, Sep 2 from Chicago to New York, returning Fri, Sep 5, priced at $153 found 1 hour ago
Southwest Airlines
Tue, Oct 28 - Thu, Oct 30
MDW
Chicago
LGA
New York
$156 Roundtrip, found 14 hours ago
$156
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Tue, Oct 28 from Chicago to New York, returning Thu, Oct 30, priced at $156 found 14 hours ago
Southwest Airlines
Wed, Aug 20 - Sat, Aug 23
MDW
Chicago
LGA
New York
$157 Roundtrip, just found
$157
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, Aug 20 from Chicago to New York, returning Sat, Aug 23, priced at $157 just found
Southwest Airlines
Tue, Sep 9 - Thu, Sep 18
MDW
Chicago
LGA
New York
$158 Roundtrip, found 2 hours ago
$158
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Tue, Sep 9 from Chicago to New York, returning Thu, Sep 18, priced at $158 found 2 hours ago
Southwest Airlines
Tue, Sep 9 - Tue, Sep 16
MDW
Chicago
LGA
New York
$162 Roundtrip, found 1 day ago
$162
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Sep 9 from Chicago to New York, returning Tue, Sep 16, priced at $162 found 1 day ago
Frontier Airlines
Fri, Oct 10 - Wed, Oct 15
MDW
Chicago
LGA
New York
$165 Roundtrip, found 2 days ago
$165
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Oct 10 from Chicago to New York, returning Wed, Oct 15, priced at $165 found 2 days ago
Delta
Tue, Sep 23 - Tue, Sep 30
MDW
Chicago
LGA
New York
$217 Roundtrip, found 5 hours ago
$217
Roundtrip
found 5 hours ago
Select Delta flight, departing Tue, Sep 23 from Chicago to New York, returning Tue, Sep 30, priced at $217 found 5 hours ago

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

October is typically the cheapest month to fly

From $110 - $382 per traveler.

Graph displaying average flight prices per month

Flights from Chicago (MDW) to New York (LGA)
Origin airport
Midway Intl.
Destination airport
LaGuardia
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$137
Distance
722 mi
Average flight time
3 hours 6 mins

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 September. 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 $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 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.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to LaGuardia Airport (LGA) cost?
Cheap round-trip fares from Midway Intl. Airport (MDW) to LaGuardia Airport (LGA) start at $135. 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 MDW on July 26 2025 and touching down at LGA. The price was last updated on June 30 2025 and has not changed since.
What is the cheapest month to fly from MDW to LGA?
To lock in a cheap fare, look for direct flights from MDW to LGA taking off in September. You can find a one-way Southwest Airlines flight for $69 leaving on September 3 2025. This price is based on the cheapest direct flight found on Expedia for this route in the next 330 days. The price was last updated on June 30 2025 and remains unchanged.
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 MDW to LGA?
With fares starting at $69 for a one-way journey from MDW to LGA, Southwest Airlines is currently the cheapest carrier for this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on September 3 2025. Prices were last updated on June 30 2025 and have not changed since.
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.

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*Available to One Key members.