Orlando to Chicago Flight Route Information
| Travel Distance: | 992 Miles |
|---|---|
| Airlines Flying This Route: | Spirit Airlines, American Airlines, Frontier Airlines |
| Weekly Flights: | 2 |
| Avg. Flight Duration: | 3.0 Hours |
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10/28/2026 Find Cheap Flights from Orlando to Chicago (ORL to CHI)
ORL - Orlando CHI - Chicago 
Find Cheap Flights from Orlando to Chicago (ORL to CHI)
Fares Starting from $102
ORL - Orlando CHI - Chicago Great deal! This is the lowest price we've seen for this one way route in the last 12 hours. Prices may change and aren't guaranteed for all flights or dates. Click on the price to continue your search and check the latest available fare. Ref. id 202609~Ref:qY2YcDD26UKtZDI1fW2S1g
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Cheap Flights from Orlando to Chicago - Compare & Book Our Best Deals
With over 47 daily departures from Orlando to Chicago, this route offers great flexibility for different travel plans. Browse one-way fares from $101.79, round-trip fares from $136.99, and other affordable options across different budgets. Compare flight choices, explore schedules, and book the best Orlando to Chicago deals that fit your budget and travel preferences.
Top Airlines that fly from Orlando to Chicago
Cheap Flight Deals from Orlando to Chicago
ORL Orlando Wed, Oct 28
CHI Chicago
from $102
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ORL Orlando Sat, Oct 31
CHI Chicago
from $102
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ORL Orlando Tue, Nov 3
CHI Chicago
from $102
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ORL Orlando Wed, Oct 21
CHI Chicago
from $102
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Fares are one way/round trip. Fares incl. all fuel surcharges, taxes & fees and our service fees. Displayed fares are subject to change and cannot be guaranteed at the time of booking. See all booking terms and conditions. 202609~Ref:qY2YcDD26UKtZDI1fW2S1g
Insights about cheap flights from Orlando to Chicago – Direct Flights, Duration & Best Travel Time
When it comes to booking cheap flights, having the right information at your fingertips can make all the difference. Dive into the insights for cheap flights from Orlando to Chicago and enhance your travel experience!
Daily Flights
47
Cheapest Month
August, March, November
Avg. Flight Duration
3.0
Peak Season
February
Distance
992 miles
Direct Flights
1407
When is the Cheapest Time to Book Flights from ORL to CHI?
Explore data-powered insights and trends for flights from Orlando to Chicago. Discover average fares, cheap months to fly, when to book, and plan smarter.
What’s the cheapest day of the week to fly from Orlando to Chicago?‡
What is the cheapest month to fly from Orlando to Chicago?‡
‡This information is based on historical data from the last 365 days.
Finding Affordable Flights from Orlando to Chicago
- Plan Ahead - One of the keys to securing cheap flights from Orlando to Chicago is to plan your trip well in advance. Airlines often offer lower prices for those who book tickets months ahead. Keep an eye on special promotions and sales events, which can yield significant savings.
- Flexibility is Key - Being flexible with your travel dates can also lead to substantial cost savings. Consider flying during off-peak seasons or on weekdays when prices tend to be lower.
- Set Price Alerts - To keep tabs on flight prices, consider setting up fare alerts. These alerts will notify you when fares from Orlando to Chicago drop, giving you the opportunity to grab cheap deals.
- Consider Nearby Airports - If Chicago has multiple airports, check the prices at each one. Sometimes, flying into a nearby airport and then taking a short train or bus ride to your destination can be a much cheaper option.
- Bundle and Save - Booking your flight and accommodation together as a package can often result in significant savings. CheapOair offers these bundled deals, so make sure to explore this option.
When should I book flights from ORL to CHI? ‡
‡Got flexible travel dates? Use our flight data from the past year to discover ideal time to fly from Orlando to Chicago. Find out which months and days typically offer lower fares and let CheapOair search for the best options.
CheapOair provides the predicted prices for one-way trips or round-trips with a duration of 7 days for domestic and 14 days for international trips based on historical data and available flight information. Graphs are estimates only. Prices are subject to change and can't be guaranteed until ticketed.
Estimated price for
Round-trip
‡Graphs are estimates only. Based on historical data and available flight information. Prices are subject to change and cannot be guaranteed until ticketed.
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Insights About Flying from Orlando to Chicago
Which is the high season to travel from Orlando to Chicago?
The month of February is considered the high season for flying from ORL to CHI. Traveling during the high season can affect ticket prices and availability, making this data crucial for trip planning.
How many direct flights are available from ORL to CHI?
There are a total of 1407 direct flights from Orlando to Chicago. For travelers seeking convenience and shorter travel times, this data is important when choosing flight options.
Which is the low season to travel from Orlando to Chicago?
August, March, November is considered the low season for traveling from Orlando to Chicago, Illinois. Travelers looking for cost-effective options and fewer crowds may consider traveling during this period.
How many daily flights are there between Orlando to Chicago?
There are as many as 47 daily flights available for travelers between ORL to CHI. This data offers flexibility in choosing departure times that best suit your schedule.
At what time does the last flight depart to Chicago?
The last flight to Chicago typically departs between 10:00PM - 11:00PM. Travelers who prefer late-night departures will find this information valuable for planning their journey.
What percentage of travelers spent an average of 3 days in Chicago, Illinois?
Approximately 34.12% of travelers spent an average of 3 days exploring Chicago. This information can assist in planning the duration of your stay in Chicago
What percentage of ORL to CHI flyers traveled with kids under 14?
About 11% of passengers on flights from Orlando to Chicago were accompanied by children under the age of 14. This information is useful if you're planning a family trip and want to know how common it is to travel with young children on this route.
What percentage of Orlando to Chicago travelers were over 60 years old?
A notable 12% of travelers were aged 60 or older. This statistic provides insights for senior travelers or those seeking a mature travel demographic.
What percentage of ORL to CHI travelers were millennials?
Millennials make up a significant portion of travelers on this route, accounting for 34% of all passengers. If you're a millennial looking to connect with like-minded travelers, this statistic might interest you.
What percentage of Orlando to Chicago travelers were female?
Almost half of the passengers, approximately 52% were female. Knowing the gender distribution can be useful for solo female travelers or those interested in gender-related travel insights.
What percent of Orlando to Chicago travellers booked first or business class?
9% of travelers booked first or business class on this route.
At what time the earliest flight departs from Orlando?
The earliest flight departs at 7:00AM - 8:00AM.
Which is the most popular airport for connecting flights between Orlando to Chicago?
Sarasota-Bradenton International Airport is the most popular airport for connecting flights between ORL to CHI.
On which days one can have the most flight options in Chicago?
Monday offer the most flight options in Chicago.
§
All flight facts are based on last 3 months' data except the highest and lowest booking months that are based on last 3 months' data.
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Cheap Flights from Orlando to Chicago
Looking for flights from Orlando (ORL) to Chicago (CHI)? Find affordable air travel deals on CheapOair and save big on air tickets online. Chicago, being the third largest city of the United States is one of the most colorful and vibrant cities in the country. From beautiful buildings, to world class museums, to great eateries and a rollicking nightlife, the city has it all. Chicago is also the ultimate destination for hard core sports and high energy festivals, especially during the months of March through September. Popular Chicago attractions include, the Museum Campus, Sears Tower, Shedd Aquarium and miles of open waterfront. To reach Chicago, CHI from Orlando, ORL you can choose from the top airlines, Spirit Airlines, AirTran Airways and American Airlines for a comfortable and convenient journey. The average time taken by a flight to cover the distance of 987 miles between the two cities is about 2 hours and 50 minutes.
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