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Not ready to book? to track prices.Find the cheapest flights from Orlando to Chicago
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Alaska Airlines flights from Orlando to Chicago
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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 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 £100, 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 May instead. Flights to Chicago in May, while not as cheap as those in September, still average around £109.
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 £203. 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 £507.
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 £265 when looking at flights departing in the morning. Flights at midday are often more expensive, with an average ticket price of £507.
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 £166 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 £118 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 44 per day as of April 2025. The most frequent departure time is 12:00, with 59% of daily flights leaving in the afternoon.
How many flights depart from Orlando to Chicago on average per week?
As of April 2025, 314 flights take off from Orlando and land in Chicago each week. The most common flight departure day for this route is Thu, with 19% 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
Is flying the fastest way to get from Orlando to Chicago?
To save time, the fastest way to travel is by flight from Orlando to Chicago on Southwest. Expect the length of time you’ll spend onboard Southwest to be about 3h 00m compared to taking a train from Orlando to Chicago or a bus from Orlando to Chicago which have been found to be slower alternatives.
Is flying the cheapest way to get from Orlando to Chicago?
A flight from Orlando to Chicago is currently going to be the least expensive option currently available. You can also find deals for a train from Orlando to Chicago starting at £192, or consider a bus from Orlando to Chicago starting at £581. Both of these alternative options are worth considering when looking to reach your destination.
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 (19.05% of total bookings). The next most popular plane models are Airbus A320neo (16.50%), Boeing 737-800 (9.62%), and Airbus A321-100/200 (8.92%).
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.