New York (LGA) to Chicago (ORD) in May 2027

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CheapestLowHigherTypical $337

$320$340$360$380

May 2027from $337 · 31 trips

New York (LGA) to Chicago (ORD): what SlickTrip has seen

Cheapest economy round trip (3 nights) in May 2027: $337 leaving Sat, May 1, for 1 traveler.
13 price drops on economy fares in the last 30 days, caught for travelers watching this route. The typical drop was $19 a traveler (6.4%).
SlickTrip travelers are watching 3 trips on this route.
Airlines in the fares we watched: American, Southwest, Delta.

From SlickTrip's own price alerts and watched trips, as of Nov 10.

New York (LGA) to Chicago (ORD) by month

November 2026
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September 2027

Cheap economy Class Flights from New York (LGA) to Chicago (ORD) May

Find the best deals on economy class flights. Compare prices for direct flights, one-stop, and multi-stop options.

New York (LGA) to Chicago (ORD) in May 2027

Cheapest round trip of 2, 3, 6 nights fare in May 2027: $337 on 2027-05-01, for 1 traveler.

Why Choose Economy Class Flights from New York (LGA) to Chicago (ORD)?

Fares across the airlines on the route in one search
Nonstop and connecting flights side by side
A month of fares at a glance for may travel
Price alerts: we watch the fare and alert you when it drops

Planning a trip from New York (LGA) to Chicago (ORD) in may? SlickTrip shows the cheapest economy fares across airlines, nonstop or with stops. Set an alert and we watch the route for you, then email you when the price drops. Booking happens on the airline's or travel site's own page.

October 2027

New York (LGA) to Chicago (ORD): what SlickTrip has seen

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