Cheapest one-way flights from New York to Chicago in May from $47

AirHint found the following cheapest one-way flights from New York (LGA) to Chicago (ORD) in May 2026 (see full year).

One-Way flights

12 May Spirit Airlines direct
05 May Spirit Airlines direct
28 May Spirit Airlines direct
30 May Spirit Airlines direct
04 May Spirit Airlines direct
14 May Spirit Airlines direct
18 May Spirit Airlines direct
16 May Spirit Airlines direct
13 May Spirit Airlines direct
20 May Spirit Airlines direct

Also check the deals for return flights from New York to Chicago in May.

Powered by

The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

Book a cheap hotel in Chicago

Cheap car rent in Chicago

Feel free to contact us with any feedback or request another flight research.