AED180 Cheap Flights from Orlando (MCO) to Chicago (MDW)

View AED180 flight on Thu, 30 October 2025Opens in a new window

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

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Cheap Flights from Orlando to Chicago (MCO-MDW)

Prices were available within the past 7 days and start at AED180 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Flights from Orlando (MCO) to Chicago (MDW)
Origin airport
Orlando Intl.
Destination airport
Midway Intl.
Distance
1585 km
Average flight time
1 hour 45 mins

Orlando to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Orlando to Chicago offer the perfect respite. Not only does exploring Chicago provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Orlando to Chicago may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from MCO to MDW today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Chicago are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Chicago more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Chicago is AED180 now!

Frequently asked questions

How long does it take to fly from Orlando Intl. Airport (MCO) to Midway Airport?
Frontier Airlines has a direct flight leaving Orlando Intl. Airport (MCO) at 3:09PM and reaching Midway Intl. Airport (MDW) at 5:05PM — a travel time of 2 hours and 56 minutes. Lock in the seat that's right for you, bring a magazine to keep you busy and the time will speed by.
Is it cheaper to buy a plane ticket from Orlando Intl. Airport to Chicago Airport last minute?
Being spontaneous is a fabulous way to travel the world, but it isn't always the wisest method to track down a cheap plane ticket. It's better to book your Orlando Intl. Airport to Chicago Airport journey well ahead of time rather than leaving it to the last minute. Based on flight pricing and demand studies in 2022, we have found that the best time to book domestic flights is between 28 – 35 days ahead of the departure date, and international flights three to four months in advance. Leave your spontaneity for when you arrive in Chicago Airport!
What airports do you fly into for Chicago from Orlando?
With Midway Intl. Airport (MDW), O'Hare Intl. Airport (ORD) and Lewis University Airport (LOT) to select from, making your way from Orlando to Chicago is simple. The city's major gateway, Midway Intl. Airport (MDW), is about 14 kilometers southwest of the downtown area. Besides ticket costs, consider factors like train or bus options from the airport and the distance to your hotel when deciding where to fly into. Get your Chicago adventure off to a flying start by exploring Wrigley Field and Millennium Park.
What are the most popular departure times for flights from Orlando Intl. Airport to Midway Airport?
The most popular departure times for flights from Orlando Intl. Airport to Midway Airport fall between 9:00 AM - 10:00 AM on Frontier Airlines. Our suggestion is to zoom off in the morning. The earlier you leave, the greater your chances of a delay-free flight as air traffic hasn't yet built up.
Can I change the date of my flight from Orlando Intl. Airport (MCO) to Chicago Airport?
It's a piece of cake to make changes to your Orlando Intl. Airport to MDW trip yourself. Simply go to the Expedia Trips portal and tap "change flight." Look for new flights and secure the one that works best. You'll get an estimate of applicable flight change fees. You can also head to our Customer Service portal to connect with our Virtual Agent and quickly get answers to your questions.

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