MDW - ORL

$49 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 9/8. 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.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Orlando

 
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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Expert advice
Booking Insights
Flight Deals

Cheap Flights from Midway 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 Midway 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Orlando

Sat, Sep 13 - Sun, Sep 21
Frontier Logo
10:51 am - 2:33 pmMDW-MCO
2h 42mnonstop
Frontier Logo
7:25 am - 9:18 amMCO-MDW
2h 53mnonstop
$94Frontier
Find Deal
Mon, Sep 8 - Sun, Sep 14
Frontier Logo
8:19 am - 12:00 pmMDW-MCO
2h 41mnonstop
Frontier Logo
7:25 am - 9:18 amMCO-MDW
2h 53mnonstop
$95Frontier
Find Deal
Sun, Sep 7 - Sun, Sep 14
Frontier Logo
10:13 am - 1:55 pmMDW-MCO
2h 42mnonstop
Frontier Logo
7:25 am - 9:18 amMCO-MDW
2h 53mnonstop
$97Frontier
Find Deal
Mon, Sep 22 - Sun, Sep 28
Frontier Logo
8:19 am - 12:00 pmMDW-MCO
2h 41mnonstop
Frontier Logo
7:25 am - 9:18 amMCO-MDW
2h 53mnonstop
$99Frontier
Find Deal
Fri, Sep 19 - Sun, Sep 21
Frontier Logo
9:48 am - 1:28 pmMDW-MCO
2h 40mnonstop
Frontier Logo
7:25 am - 9:18 amMCO-MDW
2h 53mnonstop
$100Frontier
Find Deal
Fri, Sep 12 - Sun, Sep 14
Frontier Logo
9:48 am - 1:28 pmMDW-MCO
2h 40mnonstop
Frontier Logo
7:00 am - 6:43 pmMCO-MDW
12h 43m1 stop
$101Frontier
Find Deal
Mon, Sep 15 - Sun, Sep 21
Allegiant Air Logo
12:50 pm - 9:06 pmMDW-SFB
7h 16m1 stop
Allegiant Air Logo
9:58 pm - 12:00 pmSFB-MDW
15h 02m1 stop
$215Allegiant Air
Find Deal
Fri, Nov 14 - Sun, Nov 16
Allegiant Air Logo
3:27 pm - 11:14 pmMDW-SFB
6h 47m1 stop
Allegiant Air Logo
9:55 pm - 12:02 pmSFB-MDW
15h 07m1 stop
$273Allegiant Air
Find Deal
Thu, Sep 11 - Sun, Sep 14
 Logo
8:15 am - 8:24 pmMDW-SFB
11h 09m2 stops
 Logo
9:58 pm - 12:00 pmSFB-MDW
15h 02m1 stop
Fri, Nov 21 - Sun, Nov 23
Allegiant Air Logo
2:11 pm - 8:28 pmMDW-SFB
5h 17m1 stop
Allegiant Air Logo
8:44 pm - 6:46 pmSFB-MDW
23h 02m1 stop
$297Allegiant Air
Find Deal
Expert advice

Expert advice for your flight from Midway to Orlando

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
Southwest

Southwest offers two free checked bags, saving money for travelers with luggage.


Use EarlyBird Check-In for better boarding position, avoiding middle seats.

Read more about Southwestby Blane Bachelor
Frontier

Frontier's Economy Bundle includes a carry-on and seat choice, ideal for budget travelers.


Choose Premium Bundle for priority boarding and extra legroom, just $20 more than Economy.

Read more about Frontierby Stefanie Waldek
Airports
MDW

Midway offers a user-friendly experience with shorter security lines than O'Hare, making it a convenient choice for domestic travelers.

Read more about MDWby Stefanie Waldek
MCO

MCO offers a range of transportation options including SunRail and Lynx buses, providing convenient access to Orlando's main attractions.

Read more about MCOby Jennifer Simonson
Our travel experts
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor

Blane Bachelor

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on Frontier and MDW

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Jennifer Simonson

Jennifer Simonson

Expert on MCO

Jennifer Simonson

Jennifer Simonson

Jennifer Simonson is driven by her lifelong commitment to exploring the globe. Her insatiable curiosity had led her to immerse herself into diverse locations like Oklahoma City and Pismo. Her hotel recommendations are the result of the myriad hotels she's stayed at across her travels. Along her journey, she cherishes engaging conversations with locals, indulging in the finest ice cream, trying her hand at surfing, and embarking on nature-filled hikes.

Read more
Booking Insights

KAYAK's insights & trends for Midway to Orlando flights

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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago Midway Airport to Orlando costs $97 on the route between Chicago Midway Airport (MDW) and Orlando Airport (MCO). It is also the most popular route.

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, Thursday 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 Tuesday 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 September, where tickets cost $197 (return) on average. On the other hand, the most expensive months are December and June, where the average cost of round-trip tickets is $344 and $314 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.

No, with an average price for the route of $236, prices are generally cheapest when you fly direct.

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 4 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$49
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly with an average 29% 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 $49 for a one-way ticket and $94 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, Delta, and Alaska Airlines 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 Boeing 737 MAX 8 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 Spirit Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Orlando are Southwest and Spirit Airlines. With an average price for the route of $390 and an overall rating of 8.0, Southwest is the most popular choice. Spirit Airlines is also a great choice for the route, with an average price of $267 and an overall rating of 6.3.

  • 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.

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 $81 or less one-way and $161 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Orlando?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway 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

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest, Frontier

Southwest, Frontier

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

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest, Frontier

Southwest, Frontier

Friday

Frontier, Southwest

Frontier, Southwest

Saturday

Frontier, Southwest

Frontier, Southwest

Sunday

Frontier, Southwest

Frontier, Southwest

See more direct flights

Reviews of the 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.
8.0
SouthwestOverall score based on 4242 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.0Food
7.5Entertainment
Airline reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

10.0 ExcellentKevin, Jul 2025MDW - PUJ
Read more Southwest reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

It is southwest seat was ok. Not the most comfortable seat

Plz don't take away free bags and free seating

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

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!

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

this crew didn't care much. bumping carts into seats more times than i care to remember

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

The food and sitting need improvements. They were extremely bad.. If you choose to recline, there is no room for the passenger behind you. This is one of the worst sitting arrangements that I ever experience. The aircraft was not properly clean before boarding.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

They changed my seats after I checked in and I was stressed from the time I saw that information until just before boarding, when the gate attendant fixed it, but it shouldn't have happened. And if it couldn't be prevented, then the people on the phone I spoke with should have done something to help, which they did not, nor did they offer me compensation, just meaningless apologies.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The crew was fantastic. They were there whenever we needed. The wifi didn’t work which was brutal on an 11 hour flight. The onboard entertainment was boring. Nothing of interest

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

My experience with Spirit was good, but the experience with Kayak was not. Based on the Spirit agent Kayak added an additional charge after purchasing the tickets. When I buy the tickets I paid the total amount and I only pay once. This time they added an additional charge because based on Spirit they partially charge the tickets and I still needed to pay a second time. This is not good at all and Unprofessional

Spirit gets such a bad rap. I have never had a bad experience with them and the crew is always friendly and funny. This trip I had knee replacement surgery surgery 10 weeks ago. It is still a little rough to get get from point a to point b. And Spirit was on top of it. When there was a seat available the stewardess asked me if I wanted to move to an open seat so I could elevate my leg on the empty seat? 5 stars all around. They helped me on and helped me off the plane. I can’t say enough about the crew!!

Prepaid for 1 bag but my prior airline did not provide it to me in time to check it with Spirit and I could not get my $75 refunded.

Plane delayed which seems to be the norm with spirt. Everything is an up charge. I had to pay an additional fee because I was late getting back to my car. Will never fly spirit again

It was horrible. We were not allowed on the flight by spirit staff at the gate during boarding because I had a guitar. The same guitar I had at check in which I paid for and they said I can take it on the plane. We missed our flight, lost our luggage, and had to pay another $900 to rebook flights. Worst travel experience ever and spirit staff are the worst staff ever.

The flight attendant spilled ice all down my leg and all over my suede boots and didn’t even apologize or anything. They just gave me a look like “what?!” Incredibly rude and dismissive. I saw them roll their eyes at other guests and even once yell at a lady with a baby.

Seats were comfortable but dont recline at all. Checkin online was easy but didnt provide a gate until last minute. Flight attendants were very unkind, not friendly and didnt go over safety procedures in case of a crash. No free snacks or beverages, not even water.

Good crew and safe. However, comfort and being nickeled-and-dimed are my issues. $75 each way for luggage is exhortation. The space to the next seat is so close you cannot open a laptop. The magazine rack doesn’t hold your items. Not a fan.

The booking was cancelled the next day. Spirit Airlines refunded Kayak cheapflay the full amount, but I was only refunded half. Costumer service is disgusting. Be careful. You can lose your money.

This flight went flawlessly. I don’t like thei no adjustment seats and them charging for water… but they’re a discount airline so I guess it’s to be expected

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

2 hour delay due to late plane, wrong size plane causing overbooking, and people getting off and on the plane after boarding was completed.

Since you have to pay for overhead bags then they shouldn't be running out of space and asking individuals who paid to remove stuff from the overhead

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

I chose the seats when booked the flight and paid for them. However after checking in I found we were assigned different seats!

It was a no frills flight. Would have liked to be able to charge my device

Seats were extremely uncomfortable and it was very hot on the plane.

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.