Cheap Flights from Orlando (ORL) to Chicago (MDW)

Popular airlines from Orlando Executive Airport (ORL) to Chicago Midway Airport (MDW)

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Flight from Orlando to Chicago route information
Origin airport
Orlando Executive
Destination airport
Midway Intl.
Distance
1572 km

Perfect flights from Orlando to Chicago

Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Orlando to Chicago. Whether you're aching for a romantic escape with your partner, craving an adventurous solo expedition, or yearning to immerse yourself in the local history and culture, we've got you covered.
 
Picture yourself strolling through the streets of , surrounded by breathtaking architecture and absorbing the vibrant atmosphere of this captivating city. Indulge in the mouth-watering local specialties, from tantalizing street food to exquisite fine dining. With Expedia, you can experience all of this and more, without sacrificing your budget.
 
Our flexible Orlando Executive to Midway Intl. ticket options cater to your travel preferences, with incredible one-way fares and roundtrip prices . Whether you're planning a short city break or a longer adventure, our dynamic pricing ensures that you find the best deals for your journey.
 
But the magic doesn't stop there. Expedia offers a range of partner services to enhance your trip. Rent a car at Midway Intl. and explore and its surrounding areas at your own pace. Discover hidden gems off the beaten path, and create unforgettable memories. We also provide a handpicked selection of accommodations, from charming bed and breakfasts to luxury hotels, ensuring that you have a comfortable and memorable stay.
 
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support are designed to make your travel experience seamless and stress-free. So, why wait? Book your to travel arrangements today and embark on the journey of a lifetime in Chicago.

Frequently asked questions

How much is a flight from Orlando International Airport to Chicago Airport?
If you're travelling from Orlando Executive Airport (ORL) to MDW, round-trip flights start from . This price is based on airfares available within the last 7 days on Expedia for flights departing within the next year, so don't let a good deal pass you by. Book today and save yourself both money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Orlando Executive Airport (ORL) to Midway Airport?
This differs from airline to airline, as each has its own terms and conditions. Visit the Customer Service Portal, where you'll find simple instructions on how to cancel your flight online.
How do I find cheap flights from ORL to MDW that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Orlando International Airport to MDW flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Orlando International Airport to Chicago Airport?
The flight distance between Orlando Executive Airport (ORL) and Midway Intl. Airport (MDW) is 1,600 kilometres. Bring a drink, some snacks and an interesting book to read. Keep yourself entertained and the hours will fly by.
Which airlines fly direct from ORL to Midway Airport?
Flying nonstop between Orlando Executive Airport (ORL) and MDW isn't possible at this time. However, you'll still be able to find a flight to Chicago with at least one stop.
Are Orlando Executive Airport (ORL) to Midway Intl. Airport (MDW) flight tickets cheaper when they're purchased at the last minute?
Flight prices are always on the move, so it's no sure thing. While last-minute flight deals between Orlando International Airport and Midway Airport are possible, it also makes sense to monitor prices well before you fly. In fact, some carriers release their prices up to 12 months prior to the departure date. Expedia is constantly updating the best bargains around, so keep checking back and be ready to pounce when the price is low.
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