New York to Chicago

1 ways to travelfastest 2h 47mfly from €66
Photo: Pedro Lastra / Unsplash

How the cheapest fare moved

Aug 2: €83 €83 Jul 27 Aug 2 low €66 · high €105

Departure-day prices · November 2027 New York → Chicago

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Return-day prices · November 2027 Chicago → New York

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Best time to visit Chicago — climate

Jan: ~-2°C daytime, 6 rainy days -2° JanFeb: ~0°C daytime, 6 rainy days FebMar: ~11°C daytime, 11 rainy days 11° MarApr: ~14°C daytime, 9 rainy days 14° AprMay: ~17°C daytime, 9 rainy days 17° MayJun: ~27°C daytime, 11 rainy days 27° JunJul: ~29°C daytime, 15 rainy days 29° JulAug: ~26°C daytime, 6 rainy days 26° AugSep: ~24°C daytime, 5 rainy days 24° SepOct: ~18°C daytime, 6 rainy days 18° OctNov: ~9°C daytime, 9 rainy days NovDec: ~1°C daytime, 12 rainy days Dec

Best value: Oct — fares from €66 and ~18°C daytime.

Flights from New York to Chicago start around €66 (direct flights available). Range seen recently: €66–79, based on 16 fares found by travellers.

Fly (from €66)
2h 47mduration
€66–79recent fares
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Cheapest cached fares New York → Chicago; direct flights available (e.g. B6). · Based on 16 fares found by travellers in the last 48h

Cheapest round trips to Chicago

Fares found by travellers in the last 48 hours — refreshed daily.

Sep 29 – Oct 5 Frontier Airlines · 1 stop · 4h 56m €127 Book
Aug 28 – Sep 11 Frontier Airlines · 1 stop · 4h 41m €135 Book
Sep 10 – Sep 14 Frontier Airlines · 1 stop · 6h 00m €140 Book
Aug 14 – Aug 16 United Airlines · Direct · 2h 44m €145 Book
Oct 3 – Oct 10 Frontier Airlines · 1 stop · 4h 31m €146 Book
Sep 4 – Sep 6 Frontier Airlines · 1 stop · 4h 41m €147 Book
Sep 27 – Oct 20 Frontier Airlines · 1 stop · 4h 52m €156 Book
Sep 4 – Sep 5 Frontier Airlines · 1 stop · 4h 41m €162 Book

Weather in Chicago

Sun ☁️ 22° 19° 💧2%
Mon 🌤️ 23° 18° 💧1%
Tue ☀️ 29° 18° 💧0%
Wed 🌧️ 30° 19° 💧53%
Thu 🌦️ 27° 19° 💧53%
Fri ⛈️ 29° 20° 💧15%
Sat 🌦️ 30° 20° 💧15%

Where to stay in Chicago

3★+ hotels from €114/night (38 hotels sampled, ~3 weeks out).

Warwick Allerton Chicago hotel · Chicago
from €114/night★ 4
Hotel Saint Clair - Magnificent Mile hotel · Chicago
from €145/night★ 4
ACME Hotel Chicago, Outset Collection by Hilton hotel · Chicago
from €149/night★ 4

Good to know

Time difference-1h
Time in the air2h 44m

Things to do in Chicago

Top-rated tours and tickets from €31 — book ahead for the popular ones.

Tours and tickets provided by Viator (a Tripadvisor company). Some links earn Stayonomy a commission.

About Chicago

Chicago is the home of the blues and the truth of jazz, the heart of comedy and the idea of the skyscraper. Here, the age of railroads found its center, and airplanes followed suit. "Stormy, Husky, Brawling / City of Big Shoulders," Chicago is a Heartland boomtown, its ethos defined by urban planner Daniel Burnham's immortal vision: "Make no little plans; they have no magic to stir men's blood." It is one of the world's great cities and the third largest city in the United States, behind only New York City and Los Angeles. As the hub of the Mid…

Read the full Chicago guide

Guide content from Wikivoyage contributors (CC BY-SA).

Round out the trip

Popular from New York

Cheapest destinations travellers searched recently — refreshed daily.

Flight prices are real fares travellers found in the last 48 hours, refreshed daily — the booking site confirms the final price. Train, bus and ferry fares are shown on the operators' booking sites. Weather data by Open-Meteo; exchange rates: ECB reference. Data updated 2026-08-02. Some links earn Stayonomy a commission at no cost to you.