$44 Cheap Flights from Orlando (MCO) to Chicago (ORD)

View $44 flight on Sat, May 2, 2026Opens in a new window

Popular airlines from Orlando Intl. Airport (MCO) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Orlando to Chicago (MCO-ORD)

Prices were available within the past 7 days and start at $44 for one-way flights and $88 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Wed, May 13 - Sat, May 16
MCO
Orlando
ORD
Chicago
$88 Roundtrip, just found
$88
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, May 13 from Orlando to Chicago, returning Sat, May 16, priced at $88 just found
Frontier Airlines
Wed, May 13 - Sat, May 16
MCO
Orlando
ORD
Chicago
$93 Roundtrip, just found
$93
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, May 13 from Orlando to Chicago, returning Sat, May 16, priced at $93 just found
Frontier Airlines
Wed, May 13 - Sat, May 16
MCO
Orlando
ORD
Chicago
$98 Roundtrip, just found
$98
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, May 13 from Orlando to Chicago, returning Sat, May 16, priced at $98 just found
Frontier Airlines
Fri, Apr 17 - Sat, Apr 18
MCO
Orlando
ORD
Chicago
$103 Roundtrip, found 3 hours ago
$103
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Fri, Apr 17 from Orlando to Chicago, returning Sat, Apr 18, priced at $103 found 3 hours ago
Frontier Airlines
Tue, May 12 - Fri, May 15
MCO
Orlando
ORD
Chicago
$108 Roundtrip, just found
$108
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, May 12 from Orlando to Chicago, returning Fri, May 15, priced at $108 just found
Frontier Airlines
Sat, Apr 25 - Tue, Apr 28
MCO
Orlando
ORD
Chicago
$109 Roundtrip, just found
$109
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Apr 25 from Orlando to Chicago, returning Tue, Apr 28, priced at $109 just found
Spirit Airlines
Thu, May 14 - Sat, May 16
MCO
Orlando
ORD
Chicago
$116 Roundtrip, just found
$116
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, May 14 from Orlando to Chicago, returning Sat, May 16, priced at $116 just found
American Airlines
Sat, Apr 25 - Tue, Apr 28
MCO
Orlando
ORD
Chicago
$217 Roundtrip, just found
$217
Roundtrip
just found
Select American Airlines flight, departing Sat, Apr 25 from Orlando to Chicago, returning Tue, Apr 28, priced at $217 just found
United
Sat, Apr 25 - Tue, Apr 28
MCO
Orlando
ORD
Chicago
$217 Roundtrip, just found
$217
Roundtrip
just found
Select United flight, departing Sat, Apr 25 from Orlando to Chicago, returning Tue, Apr 28, priced at $217 just found
Southwest Airlines
Sat, Apr 25 - Tue, Apr 28
MCO
Orlando
ORD
Chicago
$217 Roundtrip, just found
$217
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, Apr 25 from Orlando to Chicago, returning Tue, Apr 28, priced at $217 just found

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $235
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $235

Find the cheapest month to fly from Orlando (MCO) to Chicago (ORD)

February is typically the cheapest month to fly

From $58 - $171 per traveler.

Frequently asked questions

How much does a flight from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find cheap one-way flights from $44 and cheap return flights from $88 Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.) with Expedia. One-way flights generally range between $139 and $1207, and roundtrip flights usually range from $225 to $1180. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
August is the cheapest month to fly from Orlando (MCO) to Chicago (ORD), with average round-trip fares around $227. This price is about 17% lower than the average throughout the year, as travel demand tends to decrease during the late summer. Other affordable months to consider are February and September.*Averages based on flights available on Expedia in the last year.
Which airlines fly direct from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Choose from 4 airlines operating direct flights from MCO to ORD:

  • United operates around 83 direct flights from MCO to ORD every week
  • American Airlines operates around 48 direct flights from MCO to ORD every week
  • Spirit Airlines operates around 17 direct flights from MCO to ORD every week
  • Frontier Airlines operates around 11 direct flights from MCO to ORD every week

What is the cheapest airline that flies from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Sun Country Airlines is one of the cheapest airlines offering connecting flights from Orlando Intl. (MCO) to O'Hare Intl. (ORD), with round-trip tickets starting from around $170. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from Orlando, FL (MCO) to Chicago, IL (ORD) will differ from traveler to traveler. If you like to fly early, United offers early morning flights. If price is the most important factor, Frontier Airlines typically offers the lowest fares. American Airlines offers the most daily flights from MCO to ORD, which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
When flying from Orlando (MCO) to Chicago (ORD), August and September are the best months to consider. In August, return flights are around $227, making it a budget-friendly option. September also offers good prices and pleasant weather. These months provide a great mix of affordability and enjoyable travel experiences, based on booking data from the past year.*Prices based on flights available on Expedia in the last year.
How many flights per day from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
You can find approximately 25 nonstop flights per day from Orlando Intl. (MCO) to O'Hare Intl. (ORD). For more options, look at flights that include layovers.
What is the earliest flight from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.) typically departs at around 5:00 AM, operated by American Airlines. This seasonal service is available in July, providing an early option for travelers heading to Chicago. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from Orlando (MCO) to Chicago (ORD) are in the early morning, from 6am to 9am. About 26% of passengers prefer this time window. Many major carriers, including American Airlines and Delta, offer flights during this window. This timing works well because it allows you to arrive in Chicago with plenty of time to enjoy the city.
How long does it take to fly from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Direct flights from MCO to ORD usually take about 3 hours 20 minutes, traveling roughly 1,007 miles. If you opt for a connecting flight, expect to add around 3 hours 30 minutes to your journey. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
You can fly first class between MCO and ORD. First class cabins are available on:

  • American Airlines
  • Delta Air Lines
  • United Airlines
  • Spirit Airlines

How much is a business class flight from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
A direct, return business class ticket from Orlando, FL (MCO) to Chicago, IL (ORD) typically costs between $1,178 - $1,810 per adult. A non-stop, one-way business class flight is usually around $587 - $829 per adult. Prices often fluctuate based on seasonality and how early you book. You may also be able to find a cheaper business class journey between Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.) if you opt for a connecting flight.*Prices based on flights available on Expedia in the last year.
How do I earn miles on a Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Orlando Intl. (MCO)?
From Orlando Intl. (MCO), you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW) in Chicago. Some flights may connect through major hubs like Seattle - Tacoma Intl. (SEA), Portland Intl. (PDX), Charlotte-Douglas Intl. (CLT) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Orlando Intl.
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United
Roundtrip price
$88
Distance
1006 mi
Average flight time
2 hours 10 mins

Book with confidence

Orlando to Chicago Flights

The cheapest times to fly from Orlando to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Orlando to Chicago are during the month of May. You can find some of the cheapest flights from Orlando to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Orlando to Chicago

Sunday is one of the best days to book for cheap flights from Orlando to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Orlando to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Orlando to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $44 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Orlando to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Orlando to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Orlando to Chicago Flights

*Flight schedules are subject to change.

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*Available to One Key members.