Cheap flights from Chicago Midway to Orlando

Flights tailored to your budget

Selected dates may not give results due to COVID-19. We suggest you change the dates.
Multi-city Round trip One way
Round trip
One way
Multi-city
From
No results match your search criteria
To
No results match your search criteria
{{ weekDay }}
Dates
{{ panel.label }}
Looking for a one-way flight?

Flexible dates can save you money

Explore nearby dates to find lower fares

{{ fromDate | dateToLongNamedDate }}
?
Flexible dates
Depart {{ flexibleFromDateLabel }}
{{ option.label }}
?
Return {{ flexibleToDateLabel }}
{{ option.label }}
Passengers / Class
Number of passengers
Adults
{{ adults }}
Children
{{ children }}
Infants
{{ infants }}
Class
Economy
Available for Economy only
New Multi-city experience

Discover a new Multi-city search experience from Jetcost, designed to handle more complex itineraries. By continuing, you’ll be taken to a dedicated page powered by Kiwi.com.
How do we get the info you see here? Please note that we offer an online comparison service and that all information and prices regarding services and/or products available on our website are provided by our third-party partners. We do our best to show you up-to-date information, but please note that we are not responsible for the completeness or accuracy of the information published, so please check all conditions carefully on the website of the partner before making a booking. Please check our Terms and Conditions for more details. Read more

Find out what a flight from Chicago Midway to Orlando might cost

Prices vary based on date, airline, and availability. Compare several options if you're flying between Chicago and Orlando.

Select your dates to check current offers.

Try shifting your departure forward or backward by a day to find better options. If you’re looking for a good deal, consider flying outside peak hours as well.

Which airports near Chicago or Orlando offer flights?

In many cases, using a nearby airport can improve your chances of finding direct flights or better rates.

  • Airports in Chicago: 3 airports are active - Midway, O'Hare, Rockford.
  • Airports in Orlando: 2 options available in Orlando - Executive, Sanford.

Secondary airports can offer faster travel thanks to shorter lines and quicker boarding times than major ones.

Flights from Chicago - Midway to Orlando - Executive

Plan your journey from Chicago Midway to Orlando with ease

Use Jetcost to tailor your search — direct or connecting flights, round-trip or one-way, filtered by airline, price, travel time, or agency.

Other popular destinations

Exploring options in United States? These cities are trending: Las Vegas, Los Angeles, Miami, New York City, Orlando.

Flight availability can change quickly — refresh the results if you’ve been away from the page for a while.
Frequently Asked Questions

Frequently asked questions about flights from Chicago Midway to Orlando.

How much does an airline ticket from Chicago Midway to Orlando cost?

Flight prices can vary a lot depending on the period and destination. At the moment, this information is not available for flights from Chicago Midway to Orlando.

How far is Chicago from Orlando?

Chicago is about 983 mi from Orlando.

What are the airports in Orlando?

Orlando has 2 airports: Executive, Sanford.

What are the airports in Chicago?

Chicago has 3 airports: Midway, O'Hare, Rockford.

What are the most popular cities in United States?

The most popular cities in United States according to our users' searches are: Las Vegas, Los Angeles, Miami, New York City, Orlando.

When should I book a flight from Chicago to Orlando?

This information is not available at the moment.

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

This information is not available at the moment.

What is the most expensive month to fly from Chicago to Orlando?

This information is not available at the moment.

What is the best day of the week to fly from Chicago to Orlando?

This information is not available at the moment.