MDW - ORL

$89 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 8/12. 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
$173
Typical prices: $531-$237
Frontier
Tue 6/30Tue 7/7
MDW - MCO • 1 stop
Cheapest non-stop
$209
Typical prices: $502-$190
Southwest
Tue 7/14Tue 7/21
MDW - MCO • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Southwest includes a free carry-on; Frontier Economy Bundle adds seat choice.
Frontier Premium Bundle adds legroom and priority boarding for $20 more.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $173 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
You can fly direct with Southwest. Average duration is 2h 38m
Direct flights
Direct flights
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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
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $165 (round-trip)
Shortest trip • 4h 05m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 62% price drop
Most popular
Good to know
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Flight Deals
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Expert advice
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

Tue, Jun 30 - Tue, Jul 7
Frontier Logo
6:00 am - 6:45 am
MDW
-
MCO
23h 45m
1 stop
Frontier Logo
5:20 am - 11:07 am
MCO
-
MDW
6h 47m
1 stop
$173Frontier
Thu, Aug 6 - Mon, Aug 10
Frontier Logo
11:06 am - 7:57 pm
MDW
-
MCO
7h 51m
1 stop
Frontier Logo
5:24 pm - 10:03 pm
MCO
-
MDW
5h 39m
1 stop
$179Frontier
Thu, Aug 6 - Sat, Aug 8
Frontier Logo
11:06 am - 7:57 pm
MDW
-
MCO
7h 51m
1 stop
Frontier Logo
5:24 pm - 10:03 pm
MCO
-
MDW
5h 39m
1 stop
$181Frontier
Wed, Aug 19 - Mon, Aug 24
Frontier Logo
12:04 pm - 10:09 pm
MDW
-
MCO
9h 05m
1 stop
Frontier Logo
3:10 pm - 10:11 pm
MCO
-
MDW
8h 01m
1 stop
$182Frontier
Sat, Aug 15 - Wed, Aug 19
Frontier Logo
6:05 am - 7:57 pm
MDW
-
MCO
12h 52m
1 stop
Frontier Logo
5:10 pm - 10:11 pm
MCO
-
MDW
6h 01m
1 stop
$183Frontier
Sat, Aug 15 - Sat, Aug 22
Frontier Logo
6:05 am - 2:23 pm
MDW
-
MCO
7h 18m
1 stop
Frontier Logo
7:56 am - 10:11 pm
MCO
-
MDW
15h 15m
1 stop
$185Frontier
Thu, Jul 9 - Sun, Jul 19
Allegiant Air Logo
2:48 pm - 5:21 pm
MDW
-
SFB
25h 33m
1 stop
Allegiant Air Logo
8:58 pm - 2:38 pm
SFB
-
MDW
18h 40m
1 stop
$233Allegiant Air
Fri, Jul 17 - Sun, Jul 19
Allegiant Air Logo
3:28 pm - 11:35 pm
MDW
-
SFB
7h 07m
1 stop
Allegiant Air Logo
8:58 pm - 2:38 pm
SFB
-
MDW
18h 40m
1 stop
$245Allegiant Air
Fri, Jul 3 - Sat, Jul 11
Allegiant Air Logo
3:28 pm - 11:35 pm
MDW
-
SFB
7h 07m
1 stop
Allegiant Air Logo
8:19 pm - 1:58 pm
SFB
-
MDW
18h 39m
1 stop
$251Allegiant Air
Tue, Jun 30 - Wed, Jul 8
Multiple Airlines Logo
12:27 pm - 6:50 pm
MDW
-
SFB
29h 23m
2 stops
Multiple Airlines Logo
4:48 pm - 1:58 pm
SFB
-
MDW
22h 10m
1 stop
$303Multiple Airlines
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 $211 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 July and August, where the average cost of round-trip tickets is $110 and $105 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 $392 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 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$89
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly with an average 31% 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 5 days, the lowest price for a flight from Chicago Midway Airport to Orlando was $89 for a one-way ticket and $173 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 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 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 $370 and an overall rating of 8.0, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $246 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 $179 or less one-way and $336 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 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.
8.0
SouthwestOverall score based on 4258 reviews
8.1Boarding
7.0Food
8.6Crew
7.5Entertainment
8.0Comfort
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

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.

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.

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

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

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.

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

Information on your arrival and departure airports