$39 Find Cheap Flights from Chicago Midway Airport to Orlando

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Orlando departing on 1/6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Orlando, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Orlando, as well as popular online travel agencies
In the last 7 days travelers have searched 41,299,237 times on KAYAK, and here is why:

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Cheap Flight Deals from Chicago Midway Airport to Orlando (MDW-ORL)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago Midway Airport to Orlando that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Midway to Orlando

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to Orlando.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
10:58 am - 2:47 pmMDW-MCO
2h 49mnonstop
4:56 pm - 11:29 pmMCO-MDW
7h 33m1 stop
$93Frontier
Find Deal
Sun, Jan 12 - Sat, Jan 18
10:58 am - 2:47 pmMDW-MCO
2h 49mnonstop
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
$96Frontier
Find Deal
Sun, Jan 12 - Fri, Jan 17
12:40 pm - 4:33 pmMDW-MCO
2h 53mnonstop
5:28 pm - 7:29 pmMCO-MDW
3h 01mnonstop
$98Frontier
Find Deal
Wed, Apr 9 - Wed, Apr 16
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
12:40 pm - 6:26 pmMCO-MDW
6h 46m1 stop
$99Frontier
Find Deal
Sun, Jan 19 - Thu, Jan 23
6:10 pm - 9:50 pmMDW-MCO
2h 40mnonstop
10:25 am - 12:20 pmMCO-MDW
2h 55mnonstop
$157Southwest
Find Deal
Tue, Jan 28 - Tue, Feb 4
3:25 pm - 7:05 pmMDW-MCO
2h 40mnonstop
1:05 pm - 3:00 pmMCO-MDW
2h 55mnonstop
$163Southwest
Find Deal
Mon, Feb 3 - Wed, Feb 5
12:46 pm - 3:25 pmMDW-MCO
25h 39m1 stop
5:34 pm - 4:14 pmMCO-MDW
23h 40m1 stop
Fri, Jan 10 - Mon, Jan 13
5:05 pm - 10:38 pmMDW-MCO
4h 33m1 stop
5:30 am - 10:12 amMCO-MDW
5h 42m1 stop
$196Delta
Find Deal
Tue, Feb 11 - Wed, Feb 19
6:40 am - 3:25 pmMDW-MCO
7h 45m1 stop
9:12 am - 10:45 pmMCO-MDW
14h 33m1 stop
Fri, Jan 10 - Mon, Jan 13
6:20 pm - 2:20 pmMDW-SFB
19h 00m2 stops
9:10 am - 7:50 amSFB-MDW
23h 40m2 stops
$472Allegiant Air
Find Deal
Sun, Mar 2 - Sun, Mar 9

Flights from Midway to Orlando - Travel Insights & Trends

Get data-powered insights and trends into flights from Midway to Orlando to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago Midway Airport to Orlando flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago Midway Airport to Orlando.
Our data shows that the cheapest route for a return flight from Chicago Midway Airport to Orlando cost $114 and was between Chicago Midway Airport (MDW) and Orlando Airport (MCO). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $114.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Orlando?

The average price of all round-trip flights from Chicago Midway Airport to Orlando clicked on KAYAK for each day over the last 12 months.
For Chicago Midway Airport to Orlando, Sunday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Orlando back to Chicago Midway Airport, the best deals are generally found on Friday, with Monday being the most expensive.

What is the cheapest month to fly from Chicago Midway Airport to Orlando?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Orlando, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago Midway Airport to Orlando is May, where tickets cost $177 (return) on average. On the other hand, the most expensive months are June and December, where the average cost of round-trip tickets is $336 and $330 respectively.

Can I save money by flying with a layover from Chicago Midway Airport to Orlando?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.
Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $106 on average.

How far in advance should I book a flight from Chicago Midway Airport to Orlando?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago Midway Airport to Orlando, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.
To get a below average price on the flight from Chicago Midway Airport to Orlando, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.

Good to know

Low season

September

High season

December

Cheapest flight

$39
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 44% increase in price.
Flight from Chicago Midway Airport to Orlando Airport

When to book flights from Midway to Orlando

Are your dates flexible? Find out the best times to travel from Midway to Orlando based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Orlando flights

  • What is the cheapest flight from Chicago Midway Airport to Orlando?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Orlando was $39 for a one-way ticket and $93 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Orlando?

    A passport is required to fly from Chicago Midway Airport to Orlando.

  • Which airports will I be using when flying from Chicago Midway Airport to Orlando?

    Chicago Midway Airport is served by only 1 airport and there are 2 airports in Orlando. You will leave Chicago Midway Airport from Chicago Midway and you will be arriving in Orlando at one of these airports: Orlando or Orlando Sanford Intl.

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Orlando?

    American Airlines, JetBlue, and Delta offer inflight Wi-Fi service on the Chicago Midway Airport to Orlando flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Orlando?

    The Airbus A320neo is the aircraft model that flies most regularly on the Chicago Midway Airport to Orlando flight route.

  • On which days can I fly direct from Chicago Midway Airport to Orlando?

    There are nonstop flights from Chicago Midway Airport to Orlando on a daily basis.

  • Which is the best airline for flights from Chicago to Orlando, Southwest or Frontier?

    The two airlines most popular with KAYAK users for flights from Chicago to Orlando are Southwest and Frontier. With an average price for the route of $381 and an overall rating of 8.1, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $198 and an overall rating of 6.0.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Orlando?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Orlando.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Orlando?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Orlando from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Orlando?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Orlando with an airline and back to Chicago Midway Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Orlando?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Orlando from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to Orlando

  • Looking for a cheap flight? 25% of our users found flights on this route for $94 or less one-way and $200 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Orlando?

Find which airlines fly direct from Chicago Midway Airport to Orlando, which days they fly and book direct flights.

Direct departures

Chicago Midway to Orlando

Monday

Frontier, Southwest

Frontier, Southwest

Tuesday

Frontier, Southwest

Frontier, Southwest

Wednesday

Southwest

Southwest

Thursday

Frontier, Southwest

Frontier, Southwest

Friday

Frontier, Southwest

Frontier, Southwest

Saturday

Frontier, Southwest

Frontier, Southwest

Sunday

Frontier, Southwest

Frontier, Southwest

See more direct flights

Direct returns

Orlando to Chicago Midway

Monday

Frontier, Southwest

Frontier, Southwest

Tuesday

Frontier, Southwest

Frontier, Southwest

Wednesday

Southwest

Southwest

Thursday

Frontier, Southwest

Frontier, Southwest

Friday

Frontier, Southwest

Frontier, Southwest

Saturday

Frontier, Southwest

Frontier, Southwest

Sunday

Frontier, Southwest

Frontier, Southwest

See more direct flights
See more direct flights

Top 5 airlines serving from Midway to Orlando

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Orlando. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Orlando? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.1
SouthwestOverall score based on 4715 reviews
7.7Entertainment
8.1Comfort
8.7Crew
8.2Boarding
7.2Food
Airline reviews

It went well. Plane wasn't full. Will be great when assigned seating is in place

10.0 ExcellentJoe, Nov 2024BUF - MCO
Read more Southwest reviews

It went well. Plane wasn't full. Will be great when assigned seating is in place

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Excellent experience. WiFi worked on this leg of My trip

Flight was great, but golf bag never made it until later in the day. Even though I had a nonstop flight it was placed on a different one. They made it right with flight credits and I was able to get it the same day.

Pretty standard flight. We left late, but arrived early. The wifi entertainment is always nice. The free snacks and beverages are simple, but appreciated. I'm tall and the seats are an issue. I can deal with a short flight, but any longer, I have to find another airline where I know beforehand I have extra legroom.

The flight attendant was proactive in helping with placing carry on in overhead bins. This was the first time I had ever been offered help without asking or obviously struggling. Many on the flight were older people like myself and vertically challenged. I would hope this would be the norm on all flights.

wifi wasn't working correctly so couldn't watch live tv

Flight was delayed by 12 minutes. Boarding wasn’t fun. The crew was nice though.

The flight was promptly on schedule and Southwest delivered everything they promised. No excuses for any shortfalls just 100% ownership of their responsibilities and business. The boarding and seating policy is a complete shambles. What started out as a great idea when Southwest first hit the market has been turned into a disaster due to the lack of integrity in many of the people who fly Southwest and take advantage of Southwest generosity at the expense of their fellow passengers.

Flight was delayed more than 2 hour do the scheduling issues and then some confusing weight and balance matters, followed by a miscommunication with the tower on which runway was going to be used based on the airplane weight. All these things should have been figured out in advance. Instead of arriving at 12:30 a.m. we arrived at 2:30 a.m. very difficult to find a taxi or other transport at SFO. Luggage was delayed. An extension of an unpleasant flight day

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

Don't waste your money or points on first class. Delta first class is a joke. The seats were rickety, the food was awful, and nothing worked, wifi, my light, the power plug - and it was dirty - the fold out table was gross. For 2-3 hours, tough it out in Economy.

Loyal Delta traveler, but last nights flight was a train wreck. Seated in 1B after multiple delays. Then we couldn’t takeoff because of an issue with the passenger that was ‘not in compliance’ and had to deplane along with the threat if they did not deplane, all the passengers would be required to do so. Finally they were escorted off, but the experience threw off the crew. Disruptive for everyone. Service was a mess, televisions didn’t work, bathroom door kept swinging open during the entire flight whenever empty …

My flight was cancelled twice and the third time I tried to rebook it online I cancelled the flight because it looked like I would get a refund to my credit card. Instead I now have a credit. I was also on hold for three hours waiting for a representative and then disconnected. I will never fly delta again.

It was very cold because the air conditioner was on high power, and my son got sick.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

They did a fine job. Can't wait to use Delta in the future.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

We arrived early and finally made it to our gate almost an hour after.

Was a pain having to leave the plane and reboard but glad the plane was fixed

Plane was was better than th YVR to ORD flight but was a fraction of the distance. Fly your better planes on longer distance flights.

Nothing wrong with the flight itself. But due to 2+ hrs waiting in immigration and the additional security checkup in O’hare, I nearly missed the flight.

They need to improve their boarding process. Group 1 and/or paying first class passengers shouldn't be in the middle of boarding process

late departure due to some unspecified issue with ventilating the cabin. They got it running but it was FREEZING for the whole flight. I asked for a blanket but they didn't provide one. They could not turn up the heat. it was quite miserable.

I still prefer Delta, but Delta doesn’t fly to State College PA.

Everything was fantastic. Modern plane. All the amenities! Although the paid snacks and meals are pure robbery. Like i understand airlines need to make money, but 11$ USD for an overnight oats with some nuts in it and barely any pieces of apple.... Highway robbery

The flight was bumpy. No Breakfast or coffee was served, not even a bottle of water. The food was okay but odd. Rice with peas instead of couscous with some unknown green thing. United Airlines did not tell me that there was VERY LIMITED HANDICAP SERVICE IN NAPLES. De-plane via 20 aluminum steps. Taken to Van. You must walk into the terminal, find luggage, and then walk out to the rental car pickup spot that is 1 block from the terminal.

Lost MacBook, had time to retrieve, but was told I had no time. Need Silver MacBook back

Helpful attendants at check-in is very good. The $70 charge for a checked bags I didn't care for.and the constant charges for picking a seat and faster check-in are too much. Please cut the prices by at least 50% would be fantastic!

The MOST uncomfortable seat I've EVER experienced on ANY airlines. My wife & I were in agony at the end of the flight. NEVER AGAIN!

The flight was delayed over an hour and we had to sit on the plane. Crew does not apologize due to the delay. Spirit will NEVER do anything to give a customer a better experience. A child next to me was kicking me the whole time. I don't ever enjoy flying with Spirit.

I liked the low price. I did not like the cramped passenger seats. As a below average size person I was cramped in the seat; I can only imagine how uncomfortable an average or large size person would be. I guess that is part of the deal with low cost airlines.

Everyone on the plane was wonderful. I can't say that the trip of flying was wonderful because I hadn't done that since I was 13 years old. Honestly I was terrified. What would make it better is if they didn't drive so fast but I know they have to. And if they could go up slowly and land slowly. But none of that they can control.

Cancelled after 3 hour delay with no aside from a rebooking three days later.

Would have been better if I would’ve made it on my flight but it was delayed twice and then canceled and now I’m stuck till Monday which was and extra 5 days I did not count on .

Delays and sending me to different terminal for departures. It looked very confusing and disorganized

Arrived to destination 2.5 days late due to cancellations and delays. I was rebooked over 24 hours after the original flight. This would have happened multiple times if I wouldn’t have bit the bullet and purchased another ticket through a different airline.

Our flight was suppose to leave at 9pm and we didn’t board until after 3am. We lost a whole day at our hotel and half a day at a park we paid a lot of money for.

Boarding was organized and flight was on time. Overall very satisfied with my flight.

The boarding gate was in Terminal D, but the Frontier counter was in Terminal E. So I had to move back and forth between terminals to check in my luggage. This was the worst experience that I had in terms of flights.

Booked direct in July '24. Turned into a 14 hr layover (both ways) in Denver. My 5 day vaca turned into a 1 day . Not good, BUT,... Thank you for the people @ Frontier who were professionally friendly & approachable.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

Airline changed the gate from Terminal A to Terminal D which is quite far and only sent a text message few minutes before boarding. Around 50 people missed their flight and as plane didn’t wait for them.

The personal at boarding are rude and try to steel people with their rule of personal item , really bad experience for us

I did not like that people are purposely split ip who book at the same time because we didn’t buy seats. No other airline does that.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

Horrible my trip was delayed 3 hours, we already have set in the plane and they delayed the flight.

Book cheap flights from Chicago to Orlando

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Orlando found on KAYAK in the last 72 hours.
1/6Mon
nonstopFrontier
2h 49mMDW-MCO
$39
4/1Tue
nonstopFrontier
2h 50mMDW-MCO
$49
2/19Wed
1 stopFrontier
15h 26mMDW-MCO
$53
3/1Sat
nonstopSouthwest
2h 40mMDW-MCO
$79
2/3Mon
nonstopSouthwest
2h 40mMDW-MCO
$85
2/18Tue
1 stopDelta
5h 58mMDW-MCO
$98
1/7Tue
1 stop
6h 49mMDW-MCO
$105
2/17Mon
1 stopDelta
6h 05mMDW-MCO
$108
2/18Tue
2 stops
20h 14mMDW-MCO
$171
6/15Sun
2 stopsAllegiant Air
19h 25mMDW-SFB
$416

Search by stops

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Last minute flights from Midway to Orlando

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Orlando that are departing in the next 10 days.
1/3Fri
nonstopFrontier
2h 49mMDW-MCO
1/10Fri
nonstopFrontier
2h 55mMCO-MDW
$186
1/3Fri
nonstopFrontier
2h 49mMDW-MCO
1/10Fri
nonstopFrontier
2h 55mMCO-MDW
$190
1/4Sat
nonstopFrontier
2h 54mMDW-MCO
1/10Fri
nonstopFrontier
2h 55mMCO-MDW
$203
1/4Sat
multi-stopFrontier
8h 23mMDW-MCO
1/10Fri
nonstopFrontier
2h 55mMCO-MDW
$204
1/4Sat
nonstopFrontier
2h 54mMDW-MCO
1/12Sun
multi-stopFrontier
14h 33mMCO-MDW
$206
1/4Sat
multi-stopFrontier
8h 23mMDW-MCO
1/10Fri
nonstopFrontier
2h 55mMCO-MDW
$210
1/3Fri
multi-stopFrontier
14h 39mMDW-MCO
1/10Fri
nonstopFrontier
2h 55mMCO-MDW
$221
1/4Sat
nonstopSouthwest
2h 35mMDW-MCO
1/11Sat
nonstopSouthwest
3h 00mMCO-MDW
$562
12/31Tue
nonstopSouthwest
2h 35mMDW-MCO
1/9Thu
nonstopSouthwest
2h 55mMCO-MDW
$582
12/31Tue
multi-stopDelta
4h 01mMDW-MCO
1/7Tue
multi-stopDelta
4h 57mMCO-MDW
$616

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Everything you need to know for your flight from Midway to Orlando

Information on your arrival and departure airports

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