Cheap Flights from Orlando to Chicago (ORL - CHI)

Top last minute flight deals

Feeling spontaneous? It’s never too late to book a trip. Here’s our pick of the best last minute flights to Chicago...
Estimated lowest prices only. Found in the last 14 days.

Direct flights to Chicago

Want to fly non-stop to Chicago? We’ll help you find your ideal route.

  • Air New Zealand
  • Allegiant Air
  • American Airlines
  • ANA (All Nippon Airways)
  • Austrian Airlines
  • British Airways
  • Brussels Airlines
  • Cathay Pacific
  • Copa
  • Frontier Airlines
  • Iberia
  • Japan Airlines
  • LOT
  • Lufthansa
  • Qantas
  • Royal Jordanian
  • SAS
  • Southwest Airlines
  • Spirit Airlines
  • United
  • Volaris
Search direct flights

Flight information Orlando to Chicago

Cheapest return price last month


Direct airlines


Flights per week


Average flight time, total distance 1002 miles

2h 40min

Most popular airline last month

Southwest Airlines

Chicago O'Hare International, Chicago Midway, Chicago Rockford and Chicago Dupage County

4 airports

Frequently asked questions

There are 4 airports in Chicago: Chicago O'Hare International, Chicago Midway, Chicago Rockford, and Chicago Dupage County.
Chicago is a year-round destination. It has hot summers, lasting from June to August. During this time, temperatures often reach 29°C. Winter stretches from December to February, when temperatures can drop to around -6°C. If you want to avoid rain, January tends to be driest.
The best price found on Skyscanner for a flight from Orlando to Chicago is £58. This was found by aggregating across different carriers and is the cheapest price for the whole month.
2h 40min is the average flight time from Orlando to Chicago.
There are 6 airlines who fly direct from Orlando to Chicago.
As of February, there are 146 flights per week flying from Orlando to Chicago.

Compare flights from Orlando to Chicago and find cheap tickets with Skyscanner

Skyscanner is a fast and simple travel search engine that compares hundreds of flights from all major airlines and travel agents, finding you the best deal on cheap plane tickets to Chicago from Orlando.

Best of all, Skyscanner is free to use!

When is the best time to book from Orlando to Chicago?

Useful information before booking your travel from Orlando to Chicago

Check the travel information panel above to get exact information about:

  • Distance from Orlando to Chicago
  • Flight time to Orlando from Chicago
  • Which airlines provide the cheapest tickets from Orlando to Chicago
  • Which airlines fly direct to Chicago from Orlando.

Know your cabin luggage size and weight restrictions thanks to our guide to hand baggage.

Track your flight status by checking arrival and departure times from Orlando to Chicago

  • Stay up to date with information regarding your flight by checking our arrivals and departure boards.
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    We’ll keep you posted with the latest schedule information and send you important flight updates for your travel to Chicago from Orlando.

Book a hotel or car hire for your stay in Chicago

Need to book a hotel or car hire for your stay in Chicago? For the best hotel & car hire deals in Chicago, why not try Skyscanner?

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.