Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search over 321,000 hotels worldwide and 400 airlines worldwide.

Secure incredible value with Expedia's Price Guarantee.

No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheap MCO to MDW Flights

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Chicago

$76.58

Cheap MCO to MDW Flights

Question : How much time do people spend in Chicago?
Answer : The average time spent hanging out in Chicago by passengers from Orlando is six days. However long you decide to stay, give yourself plenty of time to see what makes Chicago fantastic.

Question : Which airline has the least delays from Orlando to Chicago?
Answer : Booking with Delta Air Lines means you will arrive to Chicago approximately the time you were supposed to. In fact, this timely airline has a 100% average on-time average. It never hurts to be prepared. If you should choose this airline, be sure to track the flight status to stay on top of the departure time.

Question : How long does it take to fly from Orlando to Chicago?
Answer : This flight takes about two hours and 45 minutes via Southwest Airlines. If you catch the 3:45 PM EST departure, you'll arrive at 5:30 PM CST. Until we get the kinks worked out of our teleportation machine, this is still the one of the fastest ways to get from Orlando to Chicago (remember, there is a one-hour time change).

Question : How long is the flight from MCO to MDW?
Answer : Southwest Airlines currently holds the fastest travel time with two hours and 45 minutes. For example, you would arrive in Chicago at 5:30 PM CST if you left Orlando at 3:45 PM EST. Remember, there is a one-hour time change.

Question : Is there an alternative airport near Chicago?
Answer : Chicago Midway International Airport is a great airport, but there is a cheaper option – O'Hare International Airport. It’s16 miles away and flights are being booked 39% cheaper over the coming two months.

Question : What is the cheapest day to fly to Chicago?
Answer : If you are looking to save some money, look at Feb 1st. As of Jan 22nd, it's showing the cheapest ticket sales at $140. That is 55% below the average for this route, so you can spend that extra money on an adventure in Chicago.

Question : Can I change the date of my flight?
Answer : You sure can adjust your departure date and you may save money by changing it. The cheapest day to fly in February is Friday. Flexibility is key when booking travel plans in order to keep costs down.

Orlando to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Orlando to Chicago will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with MCO to MDW flights that won’t make your bank account wince. Ready to temporarily leave behind Orlando for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to MDW with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.