Flights from Chicago to Orlando

Looking for flights from Chicago to Orlando? CompareWings brings you the latest offers, travel tips, non-stop airline options, and essential information to help you plan a magical journey from the Windy City to the Theme Park Capital of the World.

Route Overview

The flight route from Chicago to Orlando is one of the most popular vacation corridors in the United States. Families, snowbirds, and business travelers frequently use this route, resulting in multiple daily non-stop flight options.

The average non-stop flight duration is approximately 2 hours and 45 minutes. Departures operate from both O'Hare International Airport (ORD) and Midway International Airport (MDW), with arrivals at Orlando International Airport (MCO).

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When’s a good time to book a flight from Chicago to Orlando

What’s the cheapest day of the week to fly from Chicago to Orlando?

If you’re looking for a flight deals from Chicago to Orlando, it’s recommended to look for departures on Monday. Sunday tends to have higher prices.

What is the cheapest month to fly from Chicago to Orlando?

Historically, December has been the cheapest month for flights from Chicago to Orlando. On the other hand, the most expensive months tend to be May.

Airlines & Flight Options

Travelers have multiple airline choices ranging from premium carriers to budget-friendly options:

  • United & American Airlines – Operate major hubs at O'Hare (ORD) and offer frequent departures, premium cabins, and excellent connectivity.
  • Southwest Airlines – The main carrier at Midway (MDW), offering many non-stop flights and free checked bags, making it ideal for family travel.
  • Spirit & Frontier Airlines – Ultra-low-cost carriers operating from both ORD and MDW, offering some of the lowest fares for light travelers.
  • Delta Air Lines – Also operates flights on this route, providing more choices for SkyMiles members.

Offers, Deals & Best Ways to Save

With competition between major and budget airlines, travelers can often find excellent deals.

  • Best Booking Window – Book 2–3 months in advance for popular family travel periods to secure the best fares and flight times.
  • Cheapest Days – Tuesday and Wednesday flights are typically more affordable than weekend travel.
  • Seasonal Trends – January, February (excluding Presidents' Day weekend), and September offer lower fares and lighter crowds. Summer and Spring Break see higher prices.
  • Airport Flexibility – Compare fares between O'Hare (ORD) and Midway (MDW), as savings may offset airport travel distance.

Tips to Get the Best Deals

  • Avoid School Holidays – Flying while schools are in session can save significantly on flights and hotels.
  • Pack Light – If flying on Spirit or Frontier, pay for luggage online during booking to avoid high airport or gate fees.
  • Check One-Way Fares – It may be cheaper to fly down on one airline and return on another (e.g., United from ORD and Southwest to MDW).

Travel Tips for CHI → MCO Flyers

  • Time Zone – Chicago is in Central Time (CT), while Orlando is in Eastern Time (ET), meaning you will lose an hour when flying to Orlando.
  • Airport Transport (MCO) –
    • To Disney World – Free shuttles no longer operate; use Mears Connect, rideshares, or rental cars.
    • To Universal / International Drive – Shuttles and rideshare services are widely available.
  • Weather – Orlando summers are hot with frequent afternoon thunderstorms, while winter offers warm relief from Chicago cold.
  • Arrival Experience – MCO is a busy tourist airport. On the return trip to Chicago, arrive 3 hours early due to potentially long security lines.

Frequently Asked Questions

The average non-stop flight time is approximately 2 hours and 45 minutes.

Midway (MDW) is often preferred for its smaller size and Southwest's frequent service. O'Hare (ORD) offers more airline variety and international connection options.

Orlando International Airport (MCO) is about 20 miles from Walt Disney World Resort. The drive typically takes 30–45 minutes depending on traffic.

September is often the cheapest month due to the peak hurricane season risk and children being back in school, followed by January and February.

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