Cheap Flights from New York to Chicago (LGA to MDW) from $195.00

Planning a trip from the bustling streets of New York to the heart of the Midwest? Flying from LaGuardia Airport (LGA) to Chicago Midway International Airport (MDW) connects two iconic American cities with ease. Whether you are traveling for business meetings or eager to explore world-class museums and deep-dish pizza, Globitude Travels helps you secure the best travel arrangements for your Chicago getaway.

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Cheapest fares from New York to Chicago

Lowest fare found per airline on the LGA → MDW route, with our discounted phone-deal price.

Airline	Cabin	Found fare	Our discounted fare	Fare found on
Southwest	Economy	~~$326.00~~	$195.60	Sep 12, 2026	Book
Frontier	Economy	~~$369.98~~	$221.99	Sep 12, 2026	Book
Delta Air Lines	Economy	~~$588.80~~	$353.28	Sep 12, 2026	Book

Discounted fares are negotiated phone deals from our vendor network and may not appear in online search results — call 1-856-513-6369 to lock one in. Fares were found on the dates shown, are per person in USD, and change with availability.

Flying from New York (LGA) to Chicago (MDW)

Departing from New York via LaGuardia Airport puts you on a quick trajectory toward Chicago Midway International Airport, conveniently situated just southwest of Downtown Chicago. Midway offers a more compact, streamlined experience compared to larger hubs, allowing you to reach the Loop, Millennium Park, or trendy neighborhoods like West Loop and Logan Square with minimal transit hassle.

Chicago features distinct seasonal shifts, boasting warm, vibrant summers by Lake Michigan and crisp, snowy winters. Regardless of when you visit, the Windy City delights travelers with its famed architecture tours, thriving cultural institutions, and legendary food scene featuring deep-dish pizza and Chicago-style hot dogs. Globitude Travels makes navigating your flight options straightforward and stress-free.

Money-saving tips for this route

Book your LGA to MDW tickets at least three to four weeks in advance to secure the most competitive fares.
Take the Chicago Transit Authority (CTA) Orange Line directly from Midway Airport to downtown Chicago for an inexpensive and traffic-free commute.
Pack versatile layers, especially if traveling during spring or autumn when lakefront breezes can cause rapid temperature drops.
Consider flying mid-week on Tuesdays or Wednesdays when ticket demand and prices are typically lower.

Frequently asked questions

What is generally the cheapest month to book flights from New York to Chicago?

Shoulder seasons, particularly January through February and late autumn, often provide lower airfares and hotel rates compared to the peak summer travel months.

Which airlines operate flights between LaGuardia and Chicago Midway?

Major domestic carriers connect these two airports with frequent non-stop and connecting service; contact Globitude Travels or check real-time availability on our site for participating carriers on your selected dates.

What are the primary airports used on this route?

Flights depart from LaGuardia Airport (LGA) in Queens, New York, and arrive at Chicago Midway International Airport (MDW) on the southwest side of Chicago.

Are flights between LGA and MDW direct or do they have stops?

Both nonstop flights and single-stop connecting routes are routinely offered, allowing travelers to choose between the fastest travel time and alternate budget options.

Can I book my New York to Chicago flight over the phone with Globitude Travels?

Yes, Globitude Travels provides dedicated telephone support to assist you with reservations, itinerary customizations, and group booking needs.

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Why book with Globitude Travels

💸 Transparent pricing
The fare you see is all-inclusive — taxes and fees shown before you pay, never after.

🤝 Real travel experts
Every booking is reviewed by our team, and phone-only vendor deals can beat any online price.

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Before, during and after your trip — changes, cancellations and special requests handled by people.

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Globitude Travels is an independent travel agency — call 1-856-513-6369 or use the search above to compare live fares on this route. See our terms, privacy policy, refund policy and service fees for full details, or contact us any time.

Page updated September 6, 2026 · fare data refreshed automatically from live flight searches.