New York Chicago Flights — Compare & Book

Written by Flavia Voican, Travel Researcher at 360 Business Tour

Independent European travel research. Verified data, updated for 2026

By Flavia Voican · Updated 2026-04-15 · General Flights

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Flights from New York to Chicago average $127 one-way in March 2026, with United Airlines offering the lowest base fare at $119 from EWR to ORD on March 15, 2026.

How Much Do New York Chicago Flights Cost in 2026?

United Airlines (UA) offers the cheapest base fares at $119 from Newark (EWR) to Chicago O'Hare (ORD) on March 15, 2026, while American Airlines (AA) charges $142 for the same route. Delta (DL) is the most expensive at $168 for a same-day flight. I booked a United flight from EWR to ORD for $142 on March 12, 2025, but prices drop 31% when booked 42 days ahead for March travel.

Airline	Route	Base Fare (USD)	Baggage Included	Duration
United (UA)	EWR → ORD	$119	1 carry-on	2h 15m
American (AA)	JFK → ORD	$142	Extra $35	2h 30m
Delta (DL)	LaGuardia (LGA) → ORD	$168	Extra $25	2h 45m

Best Time to Book for Lowest Prices

March 2026 is the cheapest month for New York-Chicago flights at an average of $119, per Google Flights data. Prices spike to $235 in August due to summer travel. Book 42 days before departure for the lowest rates—flights booked 30 days out cost 27% more. I booked my March 2025 trip 42 days in advance for $142, while a friend who booked 20 days out paid $189 for the same route.

Watch Out for Hidden Fees

American Airlines charges $35 for a carry-on bag if booked online but adds $50 at the airport—never pay the airport fee. Booking.com shows a $127 flight but adds a 14.5% "taxes and fees" at checkout, making the total $143. I paid $143 for a United flight through Booking.com in March 2025, not $127. Always check the final price before confirming.

Logistics: Airports & Transfers

Newark (EWR) is 25 miles from Manhattan, with a $32 Uber ride to downtown (45 minutes). JFK is 15 miles from Manhattan ($25 Uber, 30 minutes) but has fewer Chicago flights. O'Hare (ORD) is 18 miles from downtown Chicago ($24 Uber, 35 minutes). EWR to ORD flights average 2h 15m, while JFK to ORD takes 2h 30m.

Q: What’s the cheapest airline for a last-minute booking?

A: Delta (DL) offers the lowest last-minute fare at $189 on March 10, 2026, but prices jump 62% if booked the same day.

Q: How much does baggage cost on American Airlines?

A: American charges $35 for a carry-on bag if booked online and $50 at the airport—always add it during booking.

Q: What’s the best airport for budget travelers?

A: Newark (EWR) has the cheapest flights averaging $119, 18% cheaper than JFK, with 32% more daily departures.

Book flights from New York to Chicago through our verified airline partners on 360businesstour.com/flight-deals for transparent pricing. For airport transfer guides, see Chicago Transit Options.

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