MDW - ORL

$68 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 6/3. 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, 0 bags

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
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Everything you should know

Cheapest round-trip
$148
Typical prices: $517-$287
Frontier
Mon 6/1Tue 6/9
MDW - MCO • 1 stop
Cheapest non-stop
$169
Typical prices: $332-$108
Southwest
Tue 9/15Tue 9/22
MDW - MCO • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Southwest's two free checked bags save money on luggage.
Midway's user-friendly experience features shorter lines.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $148 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
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Airline reviews
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Nonstop flights
You can fly direct with Southwest. Average duration is 2h 37m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 85% on-time
Best time • Fewest delays
Insights
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When to travel
Cheapest • 58% price drop
Most popular
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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

Mon, Jun 1 - Tue, Jun 9
Frontier Logo
6:00 am - 6:40 am
MDW
-
MCO
23h 40m
1 stop
Frontier Logo
5:10 pm - 10:11 pm
MCO
-
MDW
6h 01m
1 stop
$148Frontier
Tue, Jun 2 - Thu, Jun 4
Frontier Logo
6:00 am - 2:15 pm
MDW
-
MCO
7h 15m
1 stop
Frontier Logo
7:56 am - 10:02 pm
MCO
-
MDW
15h 06m
1 stop
$150Frontier
Wed, Jun 3 - Wed, Jun 10
Frontier Logo
12:04 pm - 7:32 pm
MDW
-
MCO
6h 28m
1 stop
Frontier Logo
5:25 am - 11:09 am
MCO
-
MDW
6h 44m
1 stop
$152Frontier
Fri, May 29 - Wed, Jun 3
Multiple Airlines Logo
3:42 pm - 10:04 am
MDW
-
MCO
17h 22m
1 stop
Multiple Airlines Logo
5:10 pm - 10:02 pm
MCO
-
MDW
5h 52m
1 stop
$159Multiple Airlines
Tue, Jun 2 - Mon, Jun 8
Frontier Logo
6:00 am - 2:15 pm
MDW
-
MCO
7h 15m
1 stop
Frontier Logo
7:56 am - 11:12 am
MCO
-
MDW
28h 16m
1 stop
$163Frontier
Wed, Jun 10 - Tue, Jun 16
Frontier Logo
12:04 pm - 6:31 pm
MDW
-
MCO
5h 27m
1 stop
Frontier Logo
5:25 am - 11:12 am
MCO
-
MDW
6h 47m
1 stop
$164Frontier
Fri, May 29 - Wed, Jun 3
Multiple Airlines Logo
3:42 pm - 10:04 am
MDW
-
MCO
17h 22m
1 stop
Multiple Airlines Logo
5:10 pm - 10:02 pm
MCO
-
MDW
5h 52m
1 stop
$165Multiple Airlines
Tue, Sep 15 - Tue, Sep 22
Southwest Logo
12:20 pm - 4:00 pm
MDW
-
MCO
2h 40mnonstop
Southwest Logo
10:20 am - 12:05 pm
MCO
-
MDW
2h 45mnonstop
$169Southwest
Fri, May 29 - Sun, May 31
Allegiant Air Logo
3:42 pm - 2:22 pm
MDW
-
SFB
21h 40m
1 stop
Allegiant Air Logo
9:11 pm - 2:52 pm
SFB
-
MDW
18h 41m
1 stop
$238Allegiant Air
Fri, May 29 - Sun, May 31
Allegiant Air Logo
3:42 pm - 2:22 pm
MDW
-
SFB
21h 40m
1 stop
Allegiant Air Logo
9:11 pm - 2:52 pm
SFB
-
MDW
18h 41m
1 stop
$239Allegiant Air
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.

How much is a round-trip flight from Chicago Midway Airport to Orlando?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Orlando departing in June.

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 $168 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 February, where tickets cost $29 (return) on average. On the other hand, the most expensive months are August and April, where the average cost of round-trip tickets is $105 and $104 respectively.

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 14 weeks before departure.

Expert advice

Expert advice for your flight from Midway to Orlando

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Blane Bachelor

Blane Bachelor

Expert on Southwest

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.

Stefanie Waldek

Stefanie Waldek

Expert on Frontier and MDW

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.

Jennifer Simonson

Jennifer Simonson

Expert on MCO

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.

Good to know

Low seasonSeptember
Cheapest flight$68
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly with an average 34% 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 $68 for a one-way ticket and $148 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, 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 Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago Midway Airport to Orlando flight route.

  • Which airline alliances offer flights from Chicago Midway Airport to Orlando?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Orlando.

  • 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 $367 and an overall rating of 7.9, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $230 and an overall rating of 5.6.

  • 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 $139 or less one-way and $285 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

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Orlando to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top 3 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.
7.9
SouthwestOverall score based on 4301 reviews
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
8.6Crew
Airline reviews

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

10.0 ExcellentMechelle, Apr 2026
MCI - PNS
Read more Southwest reviews

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

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

Everything could and should be better. We are paying for, it's not a favor, it's a service and should involve quality, responsibility and respect.

Very easy to use and convenient, you can perform any action within the same portal

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

Okay considering we had weather delays which the Pilot notified us of immediately!

N Everything was perfect from boarding to assistance to baggage in Tampa

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The whole experience was excellent. As it most often is with Delta

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

Plane was hot and miserable and the crew was rude!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

One of the worst travel experiences I've had. Had a flight scheduled with CVG to RSW on VLSWQX this morning departing at 5:30. Two individuals at the gate and one was in training. Not her fault but she didn't have the ability to check people in resulting in at least 15 families that didn't make it on the plane because they weren't checked into the system in time. When arriving at the airport to drop off our prepaid checked bags, the bag drop off agent asked if we could check our bags at the gate because of the long line. We said no problem so arrived at the gate by 5:00. They told those people that had previously paid for checked bags to stand off to the side while they let others that either didn't have a checked bag or their bag was already on the plan through. Realizing the gate workers had an issue, they either called for help or this lady showed up late for work as she didn't arrive until 5:15. The worker who had been there training the other individual and working diligently to make sure all passengers got on board. He even said that at one point all people that are currently in line are fine but asked the person in training to stand outside the ticketing area around 5:15 to notify any late travels that the flight was in boarding process and they arrrived too late. At that point, we're sill standing off to the side with our pre-paid checked bags patiently waiting. When the new lady arrived she couldn't have been more rude. It was an awful seen. Essentially they had asked for those without an assigned seat to board last, those with pre-paid checked bag stand off to the site and any traveling with a larger items that needed to be checked at the gate (such as a stroller), wait on the side. They realized that the flight needed to leave on time so the gate attendant shut the gate. So anyone without a seat assignment, those that had pre-checked bags, and the worst one I saw was a mother with two infant children was in line with use because she was asked to stand to the side because her stroller. When they shut the door to the plan they told her she could no longer get on. Her checked bags were already on the plane with her car keys in them, and the lady told her we couldn't accept anyone else on because the door was shut. She didn't even have a way to get home from the airport. Truely evil behavior. I've flown Frontier enough to know customer service is not a top priority in the company's mission, but this was an all-time low. I'm sending this after an 18 hour drive that our family just completed to Bonita Springs . I felt really bad for the lady being trained and the other individual trying to help, but when the new lady came to the gate she was truly one of the rudest individuals I've ever met. One lady had been there since 4am but because she didn't have an assigned seat they wouldn't let her on the plan.

Better than expected. Staff were friendly and nice on both flights.

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

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

Information on your arrival and departure airports