Cheapest month to fly to Chicago

The cheapest month to fly to Chicago is most often November — cheapest from 21% of the 47 origin cities we track, and an autumn month (Sep–Nov) is cheapest for 47% of them. It depends where you fly from; the cheapest right now are Miami (from 71 EUR, July); Washington (from 79 EUR, October); Boston (from 128 EUR, July); New York (from 153 EUR, June).

When is it cheapest to fly to Chicago? Below is the cheapest month and round-trip fare from 47 origin cities, from Flightmussy's 12-month fare scans. Updated 2026-06-13.

RouteCheapest monthFromYearly swing
Miami → ChicagoJuly 202671 EUR67%
Washington → ChicagoOctober 202679 EUR67%
Boston → ChicagoJuly 2026128 EUR31%
New York → ChicagoJune 2026153 EUR14%
Los Angeles → ChicagoJuly 2026178 EUR37%
Toronto → ChicagoJune 2026204 EUR24%
Mexico City → ChicagoJanuary 2027237 EUR16%
San Francisco → ChicagoNovember 2026250 EUR17%
Vancouver → ChicagoOctober 2026320 EUR24%
Bogota → ChicagoFebruary 2027376 EUR13%
Copenhagen → ChicagoAugust 2026427 EUR28%
Rio De Janeiro → ChicagoNovember 2026427 EUR20%
Dublin → ChicagoNovember 2026434 EUR29%
Rome → ChicagoOctober 2026442 EUR35%
Stockholm → ChicagoOctober 2026447 EUR6%
Paris → ChicagoAugust 2026475 EUR22%
London → ChicagoFebruary 2027486 EUR33%
Casablanca → ChicagoSeptember 2026501 EUR35%
Madrid → ChicagoNovember 2026505 EUR18%
Warsaw → ChicagoDecember 2026506 EUR12%
Gothenburg → ChicagoFebruary 2027507 EUR77%
Milan → ChicagoSeptember 2026514 EUR40%
Berlin → ChicagoAugust 2026539 EUR13%
Zurich → ChicagoAugust 2026539 EUR8%
Frankfurt → ChicagoSeptember 2026544 EUR16%
Munich → ChicagoDecember 2026546 EUR20%
Athens → ChicagoJune 2026572 EUR2%
Manchester → ChicagoNovember 2026585 EUR36%
Amsterdam → ChicagoNovember 2026590 EUR27%
Vienna → ChicagoOctober 2026601 EUR15%
Sao Paulo → ChicagoOctober 2026619 EUR32%
Helsinki → ChicagoSeptember 2026633 EUR20%
Edinburgh → ChicagoAugust 2026644 EUR20%
Dubai → ChicagoNovember 2026676 EUR29%
Singapore → ChicagoOctober 2026686 EUR40%
Delhi → ChicagoDecember 2026687 EUR18%
Lisbon → ChicagoFebruary 2027688 EUR15%
Tel Aviv → ChicagoNovember 2026720 EUR11%
Mumbai → ChicagoJanuary 2027733 EUR46%
Hong Kong → ChicagoNovember 2026749 EUR21%
Bangkok → ChicagoJanuary 2027758 EUR19%
Buenos Aires → ChicagoJuly 2026783 EUR36%
Sydney → ChicagoAugust 2026815 EUR7%
Shanghai → ChicagoAugust 20261006 EUR3%
Seoul → ChicagoAugust 20261045 EUR29%
Tokyo → ChicagoSeptember 20261088 EUR53%
Osaka → ChicagoNovember 20261150 EUR6%

Fares are round-trip estimates in EUR from 12-month scans — they change constantly; click any route to search live prices.

See also: the cheapest month to fly almost anywhere — Flightmussy's global fare-data study.

Frequently asked questions

When is the cheapest month to fly to Chicago?
November is the most common cheapest month to fly to Chicago — cheapest from 21% of 47 origin cities, with an autumn month cheapest for 47%. It varies by origin; see the per-origin table below. Updated 2026-06-13.
Where is it cheapest to fly to Chicago from?
The cheapest origins to Chicago right now are Miami (from 71 EUR, July); Washington (from 79 EUR, October); Boston (from 128 EUR, July); New York (from 153 EUR, June). Full ranked list below.
How is this calculated?
From Flightmussy's 12-month forward fare scans: for every origin city that flies to Chicago, we take the cheapest round-trip fare and the calendar month it falls in, then aggregate across 47 origins. Fares are estimates, not live quotes — click any route to search current prices.

Cheap flights and the cheapest month to fly, worldwide

About Flightmussy

Flightmussy is a free, independent flight search for travellers anywhere in the world. No signup, no ads, no tracking — email is optional, only for route price alerts. Compare fares across every airline and see 12 months of prices at a glance, including the low-cost carriers Google Flights often buries. Book directly with the airline or a trusted partner — we never add a markup.

Flight price data & research

Flightmussy runs its own 12-month forward fare scans across thousands of routes worldwide and publishes the data openly. Read the cheapest month to fly almost anywhere → — a global study of when fares are lowest — or browse the cheapest destinations from a city:

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