MDW - MCO

$77 Find Cheap Flights from Chicago Midway Airport to Orlando Airport

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 5/28. 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 Airport

 
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 24% 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.

Everything you should know

Cheapest round-trip
$162
Typical prices: $332-$121
Frontier
Tue 9/15Sat 9/19
MDW - MCO • 1 stop
Cheapest non-stop
$187
Typical prices: $332-$108
Southwest
Thu 9/17Tue 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 suit family travel.
Midway's user-friendly experience aids quick departures.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $162 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 37m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Most punctual • 85% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $165 (round-trip)
Shortest trip • 5h 15m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 34% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Orlando!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Midway to Orlando (MDW-MCO)

 
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

Tue, Sep 15 - Sat, Sep 19
Frontier Logo
7:25 am - 5:21 pm
MDW
-
MCO
8h 56m
1 stop
Frontier Logo
5:29 pm - 9:58 pm
MCO
-
MDW
5h 29m
1 stop
$162Frontier
Wed, Sep 30 - Mon, Oct 5
Frontier Logo
7:25 am - 5:21 pm
MDW
-
MCO
8h 56m
1 stop
Frontier Logo
5:29 pm - 9:58 pm
MCO
-
MDW
5h 29m
1 stop
$178Frontier
Wed, Sep 9 - Wed, Sep 16
Southwest Logo
12:35 pm - 7:20 pm
MDW
-
MCO
5h 45m
1 stop
Southwest Logo
7:35 am - 9:20 am
MCO
-
MDW
2h 45mnonstop
$181Southwest
Wed, Sep 9 - Wed, Sep 16
Southwest Logo
7:40 am - 2:35 pm
MDW
-
MCO
5h 55m
2 stops
Southwest Logo
7:35 am - 9:20 am
MCO
-
MDW
2h 45mnonstop
$186Southwest
Thu, Sep 17 - Tue, Sep 22
Southwest Logo
7:15 am - 10:45 am
MDW
-
MCO
2h 30mnonstop
Southwest Logo
7:35 am - 9:20 am
MCO
-
MDW
2h 45mnonstop
$187Southwest
Tue, Jul 7 - Wed, Jul 15
Southwest Logo
5:30 pm - 9:15 pm
MDW
-
MCO
2h 45mnonstop
Southwest Logo
8:00 am - 9:50 am
MCO
-
MDW
2h 50mnonstop
$189Southwest
Tue, Sep 8 - Tue, Sep 15
Southwest Logo
5:20 pm - 10:30 pm
MDW
-
MCO
4h 10m
1 stop
Southwest Logo
8:45 am - 1:55 pm
MCO
-
MDW
6h 10m
1 stop
$191Southwest
Thu, Sep 17 - Tue, Sep 22
Southwest Logo
1:00 pm - 7:15 pm
MDW
-
MCO
5h 15m
1 stop
Southwest Logo
5:25 pm - 7:15 pm
MCO
-
MDW
2h 50mnonstop
$193Southwest
Tue, Jul 7 - Wed, Jul 15
Southwest Logo
8:10 pm - 11:45 pm
MDW
-
MCO
2h 35mnonstop
Southwest Logo
4:40 pm - 7:50 pm
MCO
-
MDW
4h 10m
1 stop
$195Southwest
Wed, Sep 9 - Wed, Sep 16
Southwest Logo
7:40 am - 2:35 pm
MDW
-
MCO
5h 55m
2 stops
Southwest Logo
8:45 am - 1:55 pm
MCO
-
MDW
6h 10m
1 stop
$196Southwest
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 Airport?

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 Airport departing in September.

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

The average price of all round-trip flights from Chicago Midway Airport to Orlando Airport clicked on KAYAK for each day over the last 12 months.

For Chicago Midway Airport to Orlando Airport, Thursday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Orlando Airport 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 Airport?

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 Airport, 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 Airport is February, where tickets cost $193 (return) on average. On the other hand, the most expensive months are June and August, where the average cost of round-trip tickets is $419 and $382 respectively.

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

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 $401, prices are generally cheapest when you fly direct.

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

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 Airport, 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 Airport, 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, MDW and MCO

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.

Good to know

Low seasonJanuary
Cheapest flight$76
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly with an average 11% 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 Airport flights

  • What can I do after alighting in Orlando?

    Terminals A, B & C and the Gate Areas of the MCO offer numerous shops, and restaurants. The airport's city park atmosphere offers amazing views of the world. You may enjoy scenic views of downtown Orlando at the Terminal Top Parking garage. You may also relax at one of the Orlando International Airport lounges located in Gates 30-59 and other airport areas.

  • Can I smoke in the terminals of both airports?

    Orlando International Airport is a non-smoking facility according to State law. Similarly, Chicago Midway Airport does allow smoking inside the terminals. However, you can smoke outside the terminal building facility.

  • Where can I leave my luggage at Orlando International Airport?

    There is a “Hold My Luggage” spot in level 1 of terminal B. Here, you can drop/pick your luggage, store your luggage for a day/several days and luggage transfer services to your hotel or city.

  • Can I request a wheelchair at MCO?

    Yes, you should notify your airline during booking so that they arrange for assistance from their skycaps. Skycaps offers disability assistance services including wheelchair assistance, luggage transportation and other travel related needs.

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Orlando Airport was $76 for a one-way ticket and $162 for a round-trip.

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

    No

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

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

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

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago Midway Airport to Orlando Airport flight route.

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

    There are nonstop flights from Chicago Midway Airport to Orlando Airport 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 $390 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 $194 and an overall rating of 5.6.

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

    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 Airport.

  • 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 Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Orlando Airport 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 Airport?

    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 Airport with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and MCO can sometimes prove cheaper using this method.

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

    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 Airport 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 Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $179 or less one-way and $331 or less round-trip.
  • When flying from Chicago Midway Airport (MDW) to Orlando, the most popular airport of arrival is Orlando (MCO) Airport which is 8.6 miles away. This airport is centrally located southeast of downtown Orlado. Other possible airports of arrival include Orlando Sanford (SFB), St. Petersburg (PIE), Sarasota/Bradenton (SRQ and Tampa (TPA). However, these airports may have service from only a few airlines, making MCO the best option for Chicago Midway Airport to Orlando flights.
  • If you want to leave your car at the MDW airport, the long term parking option is available west of S. Cicero Avenue and north of 55th Street. In addition, there are free shuttle buses that connect the long term parking location and the main terminal building. You can call the Midway’s Parking Garage office for assistance for your parking needs.
  • There are two pet relief areas in Chicago Midway International Airport. The centrally located indoor facility iis fitted with fake grass and a pet sitting space. The outdoor facility, located before flight check-in and security, has benches and bags for travelers with pets. Despite the fact that the outdoor relief area is outside the airport’s secure area, you can just walk there in 3 minutes making pet travel easy. The airport also provides waste bags to pet owners.
  • On arrival, The Orlando International Airport has 7 seven pet relief areas. There are three outdoor areas and 4 indoor pet relief areas. Head to North Cell Lot to locate one indoor relief area and two others near the Main Terminal. The other four outdoor pet relief areas are located at the exit of Gates 1-29, 30-59, 70-99, and 100-129. Both pet relief areas are fenced, so you can let your furry companion roam free.
  • If you have a hidden disability, MCO has innovative services to help travelers with hidden disabilities, be it hearing challenges, dementia, etc. The Sunflower Lanyard program is designed to help those with hidden disorders enjoy a fulfilling flight experience at the airport.

Prefer to fly direct from Chicago Midway Airport to Orlando Airport?

 
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 Airport, 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 airlines flying 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 4276 reviews
8.0Comfort
7.0Food
8.6Crew
7.5Entertainment
8.1Boarding
Airline reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

4.0 OkayAnonymous, May 2026
MDW - LAX
Read more Southwest reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

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

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

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.

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

Other airlines flying to Orlando

Flight deals from the most popular airlines with KAYAK users flying the route