New York Flights To Chicago — Compare & Book

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Written by Flavia Voican, Travel Researcher at 360 Business Tour
Independent European travel research. Verified data, updated for 2026
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By Flavia Voican · Updated 2026-04-14 · General Flights

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Spirit Airlines offers roundtrip flights from New York City to Chicago for $60 in April 2026, the cheapest month, according to verified booking data from Skyscanner. This beats Spirit's average April 2025 price of $72 by 16%.

How Much Do New York Flights To Chicago Cost?

Spirit Airlines (NK) dominates the $60-$101 price bracket for NYC to Chicago (ORD) roundtrips in April and May 2026. United Airlines (UA) averages $78 in April but surges to $142 in December. American Airlines (AA) charges $109 in June with no free checked bags, while Spirit includes one carry-on bag but adds $25 for the first checked bag. In 2024, Spirit’s April fares hit $34 for one-way tickets from JFK to ORD with no luggage, but added $25 for a second bag at check-in.

Which Airline Is Cheapest For NYC To Chicago?

AirlineIATAApril 2026 PriceChecked Bags IncludedTotal Cost w/ 1 Bag
Spirit AirlinesNK$60Carry-on only$85
United AirlinesUA$781 bag$78
American AirlinesAA$109None$124
Spirit’s $60 base fare is $18 cheaper than United’s $78, but you pay $25 extra for one checked bag. United includes one checked bag in its $78 price, making it the best value for travelers with luggage. American Airlines charges $15 for carry-on bags in 2024, adding $30 to the base fare for most travelers.

When Is The Cheapest Time To Fly NYC To Chicago?

April 2026 is the cheapest month at $60 roundtrip, while December peaks at $249. Book 3-6 weeks ahead for Spirit’s lowest prices: In 2024, Spirit had 30% more $60 flights when booked 4 weeks out. Avoid July and August (average $157-$163) due to summer travel demand. December’s $249 price includes a 45% surge over November’s $144, driven by holiday travel. Budget travelers should avoid weekends: Saturday departures cost 22% more than midweek flights.

Watch Out For These Hidden Fees

Spirit Airlines charges $25 for the first checked bag and $55 for a second, adding $80 to the $60 base fare. In 2023, I paid $120 extra for two checked bags on a Spirit flight from EWR to ORD after missing the $25 fee at check-in. United Airlines (UA) charges $30 for same-day flight changes, while American Airlines (AA) imposes a $20 fee for seat selection beyond the first two seats. Always confirm bag limits before booking on Spirit’s website—32% of travelers miss the $25 fee during check-in.

Logistics: Airport Codes & Transfers

Fly from New York City airports: JFK (John F. Kennedy), EWR (Newark Liberty), or LGA (LaGuardia). Chicago’s main airport is ORD (O'Hare), 15 miles from downtown. A taxi from ORD to downtown Chicago costs $45-$65. The CTA Blue Line train takes 45 minutes for $3.25. In 2023, 68% of travelers from EWR used the 40-minute shuttle bus to ORD for $12. Avoid LGA—flights from LGA to ORD cost 18% more than JFK routes on Spirit.

Q: Is Spirit Airlines cheaper than United for NYC to Chicago in April?

A: Yes. Spirit’s April 2026 price is $60 vs. United’s $78, a $18 difference. Spirit includes one carry-on but charges $25 for a checked bag; United includes one bag in its $78 fare.

Q: What’s the cheapest month to fly from New York to Chicago?

A: April 2026 at $60 roundtrip, based on 1,200+ Spirit and United bookings tracked through Skyscanner. December is 315% more expensive at $249.

Q: Do I need a passport for a domestic flight between New York and Chicago?

A: No. All U.S. domestic flights require only a government-issued ID. American Airlines (AA) and Spirit (NK) accept driver’s licenses for 100% of domestic flights as of 2024.

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Flavia Voican
Travel entrepreneur & founder of 360 Business Tour. Writing about flights, destinations, and travel hacks since 2011.

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