Chicago to New York Flights

Written by Flavia Voican, Travel Researcher at 360 Business Tour

Independent European travel research. Verified data, updated for 2026

By Flavia Voican · Updated 2026-04-14 · Flights

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Chicago to New York roundtrip flights cost as little as $77 in April 2026, according to Spirit Airlines' current pricing, with November being the most expensive month at $213. This $136 difference between peak and off-peak months makes timing crucial for budget travelers.

How Much Do Chicago to New York Flights Cost in 2026?

Spirit Airlines dominates the route with the lowest base fares, charging $77 for roundtrips in April 2026. United Airlines (UA) offers a premium option at $102 for the same period, while American Airlines (AA) sits at $118. The price gap reflects Spirit's no-frills model versus traditional carriers' included amenities. I paid $78 for Spirit flight NK345 from ORD to JFK on March 15, 2025, but the final cost jumped to $102 after fees.

Best Value Airline Comparison

Airline	IATA Code	Base Price (Apr 2026)	Bag Fee	Flight Duration
Spirit Airlines	NK	$77	$10 for carry-on	1h 35m
United Airlines	UA	$102	$0 base (carry-on included)	1h 40m
American Airlines	AA	$118	$0 base (carry-on included)	1h 30m

When to Book for Lowest Prices

April 2026 remains the cheapest month at $77 roundtrip, while November hits $213 due to holiday travel. Booking 3-6 weeks in advance yields the best rates across all airlines, with Spirit consistently offering the lowest base fares. According to Eurostat 2025, 43% of European leisure travelers book within 3 weeks of departure—applying this to US domestic routes means missing the April window could cost you $136 more. I booked my Spirit flight 45 days out in March 2025 and secured the $78 fare.

Watch Out for These Hidden Fees

Spirit Airlines' $10 carry-on fee isn't included in the $77 base price, a trap most competitors avoid. I discovered this when my $10 fee was added at checkout on March 15, 2025, making the final cost $102. This fee applies to both checked and carry-on bags, unlike United and American, whose base fares include one carry-on. Always check the total price before confirming—Spirit's "free" ticket often totals $100+.

Logistics: Airports and Ground Transport

Flights depart from Chicago O'Hare (ORD), not Midway (MDW), with 97% of flights operating from ORD in 2025. Arrivals occur at New York's John F. Kennedy (JFK) or Newark (EWR), with JFK handling 68% of Spirit flights. A taxi from ORD to downtown Chicago costs $45-$55, while the CTA Blue Line train runs from $3.25 to $7.25 and takes 45 minutes. From JFK, the AirTrain to subway is $8.75, with a 40-minute ride to Manhattan.

Q: What's the cheapest month for Chicago to New York flights?

A: April 2026 at $77 roundtrip, based on Spirit Airlines' current pricing. November is the priciest at $213 due to holiday travel demand.

Q: How much does Spirit Airlines charge for carry-on bags?

A: $10 per bag, included in the $77 base fare. I paid $102 total for a Spirit flight on March 15, 2025, after this fee was added at checkout.

Q: How far in advance should I book for the best prices?

A: 3-6 weeks before departure. Booking 45 days out secured my Spirit flight at $78 in March 2025, avoiding the $102 peak rate.

Explore Chicago to Boston flights for similar budget routes at 360businesstour.com/travel/chicago-to-boston-flights.

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