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Fly from
Fly to
Route
Depart
Return
OrlandoChicago
MCO Orlando - ORD Chicago O'Hare Intl
MCOORD
Orlando
Mon 23/11
09:00-13:32
1 stop5h 32m
Chicago O'Hare Intl
Fri 27/11
14:59-22:19
1 stop6h 20m
OrlandoChicago
MCO Orlando - ORD Chicago O'Hare Intl
MCOORD
Orlando
Fri 11/12
18:50-23:33
1 stop5h 43m
Chicago O'Hare Intl
Wed 16/12
14:59-22:08
1 stop6h 09m
OrlandoChicago
MCO Orlando - ORD Chicago O'Hare Intl
MCOORD
Orlando
Mon 9/11
18:54-23:36
1 stop5h 42m
Chicago O'Hare Intl
Wed 11/11
13:00-23:59
1 stop9h 59m
OrlandoChicago
MCO Orlando - ORD Chicago O'Hare Intl
MCOORD
Orlando
Thu 12/11
08:07-18:45
1 stop11h 38m
Chicago O'Hare Intl
Wed 16/12
08:15-20:53
1 stop11h 38m
OrlandoChicago
MCO Orlando - ORD Chicago O'Hare Intl
MCOORD
Orlando
Sun 15/11
18:54-23:50
1 stop5h 56m
Chicago O'Hare Intl
Tue 17/11
13:00-22:59
1 stop8h 59m
OrlandoChicago
MCO Orlando - ORD Chicago O'Hare Intl
MCOORD
Orlando
Sun 8/11
18:54-23:50
1 stop5h 56m
Chicago O'Hare Intl
Wed 11/11
13:00-23:59
1 stop9h 59m
OrlandoChicago
MCO Orlando - ORD Chicago O'Hare Intl
MCOORD
Orlando
Wed 25/11
18:15-23:38
1 stop6h 23m
Chicago O'Hare Intl
Tue 1/12
14:59-22:08
1 stop6h 09m
OrlandoChicago
MCO Orlando - ORD Chicago O'Hare Intl
MCOORD
Orlando
Mon 7/12
18:50-23:33
1 stop5h 43m
Chicago O'Hare Intl
Thu 10/12
14:59-22:08
1 stop6h 09m
OrlandoChicago
MCO Orlando - ORD Chicago O'Hare Intl
MCOORD
Orlando
Tue 1/12
18:50-23:33
1 stop5h 43m
Chicago O'Hare Intl
Thu 10/12
14:59-22:08
1 stop6h 09m
OrlandoChicago
MCO Orlando - ORD Chicago O'Hare Intl
MCOORD
Orlando
Mon 9/11
18:54-23:36
1 stop5h 42m
Chicago O'Hare Intl
Tue 10/11
14:59-22:24
1 stop6h 25m
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?
Prices are currently typical for flights on this route.
Typical prices usually range from £79 to £260.The lowest price recently found on this route was £151.
What is the cheapest month to fly to Chicago?
The cheapest month to fly to Chicago from Orlando is in February. Flight prices, which tend to average around £127, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of February, then book flights to Chicago from Orlando during January instead. Flights to Chicago in January, while not as cheap as those in February, still average around £132.
What is the cheapest Orlando to Chicago flight route?
Fly from Orlando to Chicago Midway for the best Orlando - Chicago flight prices
How far in advance should I book a flight from Orlando to Chicago?
You are more likely to see cheaper flights to Chicago from Orlando when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around £196 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Orlando for as low as £172 on momondo.
What cabin class options are available on Orlando to Chicago flights?
There are 3 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 often are flights from Orlando to Chicago delayed?
Historically, on average around 18% of flights between Orlando and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 144 minutes.
What is the most punctual flight time for Orlando to Chicago flights?
Generally, flights departing in the morning tend to experience fewer delays. Flights departing in the evening have, in the past, seen delays more frequently in comparison.
What day of the week experiences the fewest flight delays on this route?
Wednesday is statistically the day of the week that experiences the fewest delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.
Which airline has the best punctuality record on Orlando to Chicago flights?
According to our data, United Airlines have had the fewest delays on this route over the last 12 months, with about 9% of their flights experiencing any sort of delay.
How many flights depart from Orlando to Chicago on average per day?
The number of flights available between Orlando and Chicago is 55 per day as of October 2026. The most frequent departure time is 14:00, with 45% of daily flights leaving in the afternoon.
How many flights depart from Orlando to Chicago on average per week?
As of October 2026, 391 flights take off from Orlando and land in Chicago each week. The most common flight departure day for this route is Fri, with 18% 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
Frequently asked questions about flying 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 10m 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 (21.14% of total bookings). The next most popular plane models are Boeing 737-800 (11.93%), Airbus A321-100/200 (11.46%), and Boeing 737 MAX 8 (8.77%).
Travelling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy 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.