Chicago to Orlando

1 ways to travelfastest 2h 36mfly from €40
Photo: Mick Haupt / Unsplash

When is it cheapest to fly?

Jul: from €115 — show this month's calendar €115 JulAug: from €40 — show this month's calendar €40 AugOct: from €108 — show this month's calendar €108 OctNov: from €69 — show this month's calendar €69 NovFeb: from €118 — show this month's calendar €118 FebMay: from €148 — show this month's calendar €148 May

How the cheapest fare moved

Jul 22: €42 €42 Jul 16 Jul 22 low €40 · high €146

Departure-day prices · January 2027 Chicago → Orlando

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Cheapest days highlighted · darker = pricier · past days greyed out · cached one-way fares.

Return-day prices · January 2027 Orlando → Chicago

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Best time to visit Orlando — climate

Jan: ~18°C daytime, 5 rainy days 18° JanFeb: ~25°C daytime, 9 rainy days 25° FebMar: ~26°C daytime, 6 rainy days 26° MarApr: ~30°C daytime, 3 rainy days 30° AprMay: ~32°C daytime, 19 rainy days 32° MayJun: ~32°C daytime, 21 rainy days 32° JunJul: ~32°C daytime, 21 rainy days 32° JulAug: ~32°C daytime, 27 rainy days 32° AugSep: ~30°C daytime, 20 rainy days 30° SepOct: ~28°C daytime, 10 rainy days 28° OctNov: ~25°C daytime, 3 rainy days 25° NovDec: ~23°C daytime, 5 rainy days 23° Dec

Best value: Aug — fares from €40 and ~32°C daytime.

Flights from Chicago to Orlando start around €40 (direct flights available). Range seen recently: €40–88, based on 5 fares found by travellers.

Fly (from €40)
2h 36mduration
€40–88recent fares
Book
Cheapest cached fares Chicago → Orlando; direct flights available (e.g. G4). · Based on 5 fares found by travellers in the last 48h

Cheapest round trips to Orlando

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

Aug 14 – Aug 17 Allegiant Air · Direct · 2h 39m €89 Book
Sep 26 – Oct 1 Frontier Airlines · Direct · 2h 53m €120 Book
Aug 22 – Aug 31 Frontier Airlines · Direct · 3h 12m €121 Book
Sep 1 – Sep 4 Frontier Airlines · Direct · 2h 45m €122 Book
Aug 27 – Aug 31 Frontier Airlines · Direct · 2h 45m €123 Book
Aug 20 – Aug 24 Frontier Airlines · Direct · 2h 45m €123 Book
Aug 21 – Aug 23 Allegiant Air · Direct · 2h 36m €126 Book
Aug 26 – Aug 31 Frontier Airlines · Direct · 3h 12m €138 Book

Weather in Orlando

Wed 🌤️ 36° 24° 💧12%
Thu ☁️ 35° 24° 💧18%
Fri ☁️ 37° 26° 💧23%
Sat 🌧️ 36° 26° 💧46%
Sun ⛈️ 33° 24° 💧44%
Mon ⛈️ 35° 24° 💧40%
Tue 🌦️ 36° 26° 💧45%

In Jan, Orlando typically sees ~21°C daytime highs and 5 rainy days.

Where to stay in Orlando

3★+ hotels from €37/night (39 hotels sampled, ~3 weeks out).

Ramada by Wyndham Kissimmee Gateway - Free Theme Park Shuttle hotel · Orlando
from €37/night★ 3
See availability
Best Western Orlando Gateway Hotel hotel · Orlando
from €46/night★ 4
See availability
Avanti International Resort hotel · Orlando
from €48/night★ 3
See availability

Good to know

Time difference+1h
Time in the air2h 36m

Things to do in Orlando

Top-rated tours and tickets from €62 — book ahead for the popular ones.

from €401
Private Lake Okeechobee Fishing Trip From Orlando★ 5.0 (61)
from €459
Private Orlando Fishing Charter on Butler Chain of Lakes★ 5.0 (58)
from €579
Private 6-Hour Butler Chain Bass Charter Near Orlando★ 5.0 (49)
from €85
Food Tour of Local Orlando's Ivanhoe Village★ 5.0 (46)
from €62
Private Orlando Airport Transfer to Disney Resort Area★ 5.0 (45)
from €397
Private St. Johns River Bass Charter Near Daytona Beach★ 5.0 (41)

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

About Orlando

For the broader urban area including suburbs and other nearby destinations, please see the Greater Orlando article. Orlando deserves its reputation as the theme park capital of the world, with an estimated 52 million visitors a year. The city is best known for its theme parks Walt Disney World and Universal Orlando, but it holds a lot to offer besides those two amusement meccas. Countless hotels and restaurants cater to business conventions and other events hosted by organizations from all over the country.

Read the full Orlando guide

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

Round out the trip

eSIM for OrlandoData from the moment you land — no roaming bills. Rent a car in OrlandoCompare local and international rental desks. Airport transferFixed-price pickup waiting at arrivals. Travel insuranceMedical + luggage cover from a few €/day.

Popular from Chicago

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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 2026-07-22. Some links earn Stayonomy a commission at no cost to you.