Save money when you book flights with momondo
Big names, great deals
Big names, great deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customise your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Orlando to Chicago
Cheap return flights
Cheap one-way flights
Cheap last-minute flights
Cheap direct flights
Delta flights from Orlando to Chicago
Our best Delta deals on Orlando to Chicago flight tickets
Southwest flights from Orlando to Chicago
Our best Southwest deals on Orlando to Chicago flight tickets
See travel insights to Chicago from
How to get the cheapest flight ticket from Orlando to Chicago
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Orlando and Chicago?
What is the cheapest month to fly to Chicago?
The cheapest month to fly to Chicago from Orlando is in September. Flight prices, which tend to average around £98, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of September, then book flights to Chicago from Orlando during August instead. Flights to Chicago in August, while not as cheap as those in September, still average around £118.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as £149. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Thursday, with ticket prices averaging around £407.
What is the cheapest time of day to depart on your flight to Chicago?
Flying to Chicago from Orlando in the morning is the least expensive time of day to depart. momondo users have found prices as low as £258 when looking at flights departing in the morning. Flights at midday are often more expensive, with an average ticket price of £494.
What is the cheapest Orlando to Chicago flight route?
Fly from Orlando to Chicago O'Hare Intl for the best Orlando - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Orlando when booking 13 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around £164 when searching 13 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Orlando for as low as £138 on momondo.
What cabin class options are available on Orlando to Chicago flights?
There are 2 cabin classes available to choose from on Orlando to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
How many flights depart from Orlando to Chicago on average per day?
The number of flights available between Orlando and Chicago is 50 per day as of June 2025. The most frequent departure time is 14:00, with 50% of daily flights leaving in the afternoon.
How many flights depart from Orlando to Chicago on average per week?
As of June 2025, 354 flights take off from Orlando and land in Chicago each week. The most common flight departure day for this route is Thu, with 17% of weekly flights taking off on this day.
When to book flights from Orlando to Chicago
Cheap Orlando to Chicago (ORL to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Orlando to Chicago
How far is Orlando to Chicago by plane?
The distance between Orlando and Chicago is about 985.3 mi. Typically, this will take 3h 00m by plane in normal conditions.
When did momondo last update prices for flights from Orlando to Chicago?
Prices for flights from Orlando to Chicago refresh daily.
How old do you have to be to fly from Orlando to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Orlando to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Orlando to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Orlando to Chicago is Airbus A321neo (20.77% of total bookings). The next most popular plane models are Airbus A320neo (14.11%), Boeing 737 MAX 8 (10.17%), and Boeing 737-800 (9.96%).
Why use momondo?
Why should I use momondo to find a flight deal from Orlando to Chicago?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Orlando to Chicago. momondo saves you time and could save you money on your trip.
Can I find flights from Orlando to Chicago with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Chicago from Orlando with this policy.
How can momondo help me find flights from Orlando to Chicago?
momondo provides multiple filters to help you find the best flight to Chicago from Orlando. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Orlando to Chicago right now. Can momondo alert me if prices change?
If you are not ready to book a flight from Orlando to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.