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CA $180 Cheap Flights from Orlando (MCO) to Chicago (MDW)

View CA $180 flight on Sat, Sep 5, 2026Opens in a new window

Popular airlines from Orlando International Airport (MCO) to Chicago Midway Airport (MDW)

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Cheap flights from Orlando (MCO) to Chicago (MDW)

Prices were available within the past 7 days and start at CA $180 for one-way flights and CA $417 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Sep 15 - Sat, Sep 19
MCO
Orlando
MDW
Chicago
CA $417 Roundtrip, found 17 hours ago
CA $417
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Tue, Sep 15 from Orlando to Chicago, returning Sat, Sep 19, priced at CA $417 found 17 hours ago
Delta
Tue, Sep 15 - Sat, Sep 19
MCO
Orlando
MDW
Chicago
CA $418 Roundtrip, found 17 hours ago
CA $418
Roundtrip
found 17 hours ago
Select Delta flight, departing Tue, Sep 15 from Orlando to Chicago, returning Sat, Sep 19, priced at CA $418 found 17 hours ago
Delta
Sat, Nov 21 - Mon, Nov 23
MCO
Orlando
MDW
Chicago
CA $424 Roundtrip, found 17 hours ago
CA $424
Roundtrip
found 17 hours ago
Select Delta flight, departing Sat, Nov 21 from Orlando to Chicago, returning Mon, Nov 23, priced at CA $424 found 17 hours ago
Southwest Airlines
Sat, Nov 21 - Mon, Nov 23
MCO
Orlando
MDW
Chicago
CA $424 Roundtrip, found 17 hours ago
CA $424
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Sat, Nov 21 from Orlando to Chicago, returning Mon, Nov 23, priced at CA $424 found 17 hours ago
Southwest Airlines
Tue, Sep 15 - Sat, Sep 19
MCO
Orlando
MDW
Chicago
CA $439 Roundtrip, found 17 hours ago
CA $439
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Tue, Sep 15 from Orlando to Chicago, returning Sat, Sep 19, priced at CA $439 found 17 hours ago
Southwest Airlines
Tue, Sep 15 - Sat, Sep 19
MCO
Orlando
MDW
Chicago
CA $445 Roundtrip, found 17 hours ago
CA $445
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Tue, Sep 15 from Orlando to Chicago, returning Sat, Sep 19, priced at CA $445 found 17 hours ago
Delta
Tue, Sep 15 - Sat, Sep 19
MCO
Orlando
MDW
Chicago
CA $445 Roundtrip, found 17 hours ago
CA $445
Roundtrip
found 17 hours ago
Select Delta flight, departing Tue, Sep 15 from Orlando to Chicago, returning Sat, Sep 19, priced at CA $445 found 17 hours ago
Delta
Tue, Sep 15 - Sat, Sep 19
MCO
Orlando
MDW
Chicago
CA $447 Roundtrip, found 17 hours ago
CA $447
Roundtrip
found 17 hours ago
Select Delta flight, departing Tue, Sep 15 from Orlando to Chicago, returning Sat, Sep 19, priced at CA $447 found 17 hours ago
Southwest Airlines
Tue, Sep 15 - Fri, Sep 18
MCO
Orlando
MDW
Chicago
CA $452 Roundtrip, found 17 hours ago
CA $452
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Tue, Sep 15 from Orlando to Chicago, returning Fri, Sep 18, priced at CA $452 found 17 hours ago
Southwest Airlines
Tue, Aug 25 - Tue, Sep 1
MCO
Orlando
MDW
Chicago
CA $456 Roundtrip, found 17 hours ago
CA $456
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Tue, Aug 25 from Orlando to Chicago, returning Tue, Sep 1, priced at CA $456 found 17 hours ago

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city centre is 23 minutes. Flights from CA $444
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from CA $444

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

April is typically the cheapest month to fly

From CA $123 - CA $327 per traveller.

Frequently asked questions

How much does a flight from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find one-way and return flights from MCO to MDW with Expedia. 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 our cheapest fares first, and use the Price Tracking tool to receive alerts when MCO to MDW ticket fares go up or down.
What is the cheapest month to fly from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (MDW-Midway Intl.)?
The cheapest months to fly from MCO to MDW are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (MDW-Midway Intl.)?
There are 2 airlines offering direct flights from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (MDW-Midway Intl.). These include:
  • Southwest Airlines operates 52 direct flights from MCO to MDW every week.
  • Frontier Airlines operates 7 direct flights from MCO to MDW every week.
What is the cheapest airline that flies from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (MDW-Midway Intl.)?
Frontier Airlines is one of the cheapest airlines offering nonstop return flights from Orlando International Airport (MCO) to Chicago Midway International Airport (MDW), with tickets starting from around CA$88 for flights that can be booked for departure within the next year. Frontier Airlines also offers one of the cheapest connecting return flights from Orlando International Airport (MCO) to Chicago Midway International Airport (MDW) starting from around CA$135. These prices are per adult, for economy/coach class. 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.
How do I find cheap flights from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (MDW-Midway 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 (MDW-Midway Intl.)?
The best airline to fly with from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (MDW-Midway Intl.) will differ from traveler to traveler. If you like to fly early, Southwest Airlines offers early morning flights. If price is the most important factor, Frontier Airlines typically offers the lowest fares. Southwest Airlines offers the most daily flights from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (MDW-Midway Intl.), 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 (MDW-Midway Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (MDW-Midway Intl.)?
You'll find approximately 8 nonstop flights per day from Orlando International Airport (MCO) to Chicago Midway International Airport (MDW). For even more choices, look at flights that include layovers, as there are around 143 connecting flights per day. Some common connection points include Baltimore Washington International Thurgood Marshall (BWI), Hartsfield-Jackson Atlanta International (ATL), and Nashville International (BNA).
What is the earliest flight from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (MDW-Midway Intl.) typically departs around 5:00 AM. This service is operated by Frontier Airlines. This is a seasonal service active in October and November. An early departure like this can help you make the most of your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (MDW-Midway Intl.)?
You'll typically find the most flights from Orlando International Airport (MCO) to Midway International Airport (MDW) on a Friday, with around 84 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include Southwest Airlines, Delta, and United. Fridays offer notably more flight options compared to other days of the week, so if you're looking for the widest selection, that's a great day to consider.
What are the most popular departure times for flights from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Orlando Intl. (MCO) to Midway Intl. (MDW) are in the morning, from 6am to 9am. Many major carriers, including Southwest Airlines, Delta and Frontier Airlines, offer flights during this window. Many travellers prefer these early morning flights as they allow you to arrive at your destination with plenty of time to start your day.
How long does it take to fly from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (MDW-Midway Intl.)?
A nonstop flight from Orlando International Airport (MCO) to Midway International Airport (MDW) typically takes around 2 hours 48 minutes. This route covers a distance of approximately 1,595 kilometers (about 991 miles). If you opt for a one-stop flight, your travel time will be longer, usually around 7 hours 30 minutes. Flights with two or more stops take even longer, averaging about 11 hours 48 minutes. Keep in mind that actual flight times can vary due to factors like wind patterns and air traffic, so it's always a good idea to allow for some extra time when planning your trip.
Can you fly business or first class from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (MDW-Midway Intl.)?
You can fly business class or first class between MCO and MDW. You can fly business class with Frontier Airlines and Delta.First class cabins are available on Delta.
How do I earn miles on a Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (MDW-Midway 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, IL (MDW) from Orlando, FL (MCO)?
If you're planning to travel to Chicago from Orlando Intl. (MCO), you can fly directly into Midway Intl. (MDW). Some flights may connect through major hubs like Baltimore Washington Intl. Thurgood Marshall (BWI), Nashville Intl. (BNA), or Love Field (DAL) 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 (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (MDW-Midway 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 (MDW-Midway Intl.) flight and hotel package?
Securing a Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package 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 (MDW-Midway Intl.)?
If you booked your Orlando, FL (MCO-Orlando Intl.) to Chicago, IL (MDW-Midway 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
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
CA $417
Distance
1585 km
Average flight time
1 hour 47 mins

Book with confidence

Orlando to Chicago Flights

The easy way to book your flights from Orlando to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from Orlando whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to Midway Intl., too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Orlando to Chicago today, tomorrow, or this week.  

 

Save dollars with cheap flights from Orlando Intl., MCO to Midway Intl., MDW 

Sort your search results by price to find great deals on your flight from Orlando to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Orlando currently is just CA $417 rising to CA $456.  

Here are more money-saving tips: 

  • Fly in September when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Chicago  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Chicago from Orlando 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today.

Orlando to Chicago Flights

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*Available to Expedia members.