Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline Spirit Airlines

The cheapest airline(s) flying from Orlando to Chicago is Spirit Airlines.

  • Spirit Airlines Spirit Airlines
  • United Airlines United Airlines
  • JetBlue Airways JetBlue Airways
  • Sun Country Airlines Sun Country Airlines
  • American Airlines American Airlines
  • Southwest Airlines Southwest Airlines
Cheapest Month May

Travel Period: February 2025 - January 2026

The cheapest month(s) to fly from Orlando to Chicago is May.

  • Feb 2025
  • Mar 2025
  • Apr 2025
  • May 2025
  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
  • Oct 2025
  • Nov 2025
  • Dec 2025
  • Jan 2026
Cheapest Day of the Week Friday

The cheapest day(s) of the week to fly from Orlando to Chicago is Friday.

  • Sun Sunday
  • Mon Monday
  • Tue Tuesday
  • Wed Wednesday
  • Thu Thursday
  • Fri Friday
  • Sat Saturday
What’s the most popular airline flying from Orlando to Chicago?

The most popular airline flying from Orlando to Chicago is Frontier Airlines. Find the latest flight deals on Wego.

How far is Chicago from Orlando?

The flight distance between Orlando and Chicago is 1587km. Check all available flights on Wego.

Popular Airlines Flying From Orlando to Chicago

Frontier Airlines ‏()
Spirit Airlines ‏()
American Airlines ‏()
United Airlines ‏()

Popular Destinations From Chicago

Popular Destinations From Orlando

Popular Hotels in Chicago

Hotels In Popular Destinations