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Find cheap flights from Chicago Midway Airport to Orlando from $34

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 4/9. 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
0 bags
Sat 4/27
Sat 5/4

Search 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
In the last 7 days travelers have searched 47,584,047 times on KAYAK, and here is why:

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Cheap flight deals from Midway to Orlando

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 and deals for you by selecting your travel dates.
Choose your dates
6:08 pm - 1:03 amMDW-MCO
5h 55m1 stop
5:01 am - 6:54 amMCO-MDW
2h 53mnonstop
$84Frontier
Find Deal
Wed, May 15 - Wed, May 22
12:28 pm - 11:33 pmMDW-MCO
10h 05m1 stop
5:01 am - 6:54 amMCO-MDW
2h 53mnonstop
$85Frontier
Find Deal
Wed, May 15 - Wed, May 22
3:11 pm - 7:01 pmMDW-MCO
2h 50mnonstop
5:30 pm - 7:27 pmMCO-MDW
2h 57mnonstop
$88Frontier
Find Deal
Tue, Apr 9 - Sat, Apr 13
4:36 pm - 12:44 amMDW-MCO
7h 08m1 stop
9:55 am - 11:52 amMCO-MDW
2h 57mnonstop
$89Frontier
Find Deal
Wed, Apr 10 - Thu, Apr 11
10:22 pm - 6:30 amMDW-MCO
7h 08m1 stop
9:23 am - 1:53 pmMCO-MDW
5h 30m1 stop
Thu, Apr 11 - Tue, Apr 16
4:36 pm - 12:44 amMDW-MCO
7h 08m1 stop
6:48 am - 1:53 pmMCO-MDW
8h 05m2 stops
Wed, Apr 10 - Tue, Apr 16
8:45 am - 4:19 pmMDW-MCO
6h 34m1 stop
6:30 am - 12:40 pmMCO-MDW
7h 10m1 stop
$198Delta
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Thu, May 30 - Sun, Jun 2
6:48 pm - 12:25 amMDW-MCO
4h 37m1 stop
8:15 am - 12:40 pmMCO-MDW
5h 25m1 stop
$232Delta
Find Deal
Mon, Jun 3 - Wed, Jun 5
9:07 pm - 5:21 pmMDW-SFB
19h 14m1 stop
9:51 am - 8:17 pmSFB-MDW
11h 26m1 stop
$262Allegiant Air
Find Deal
Fri, Apr 12 - Mon, Apr 15
9:07 pm - 5:21 pmMDW-SFB
19h 14m1 stop
6:19 pm - 4:31 pmSFB-MDW
23h 12m2 stops
$297Allegiant Air
Find Deal
Fri, Apr 12 - Sun, Apr 14

Flights from Midway to Orlando - Travel Insights & Trends

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

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

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Chicago Midway Airport to Orlando.
Our data shows that the cheapest route for a one-way flight from Chicago Midway Airport to Orlando cost $35 and was between Chicago Midway Airport and Orlando Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $67.

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

The average price of all flights from Chicago Midway Airport to Orlando clicked on KAYAK for each day over the last 12 months.
For Chicago Midway Airport to Orlando, Tuesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Orlando back to Chicago Midway Airport, the best deals are generally found on Thursday, with Sunday 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 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 January, where tickets cost $174 on average. On the other hand, the most expensive months are March and June, where the average cost of tickets is $289 and $260 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for 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 month.
To get a below average price on the flight from Chicago Midway Airport to Orlando, you should book around 5 days before departure. For the absolute cheapest price, our data suggests you should book 11 days before departure.

Which airlines provide the cheapest flights from Chicago Midway Airport to Orlando?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Frontier ($34) and Delta ($88). The cheapest round-trip tickets were found on Frontier ($84) and Delta ($198).

Which airlines fly non-stop between Chicago Midway Airport and Orlando?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Chicago Midway Airport to Orlando.
There are 2 airlines that fly nonstop from Chicago Midway Airport to Orlando. They are Frontier and Southwest. The cheapest airline for this route is Frontier, with the best one-way deal found costing $72. On average, the best prices for this route can be found at Frontier.

How many flights are there between Chicago Midway Airport and Orlando per day?

Each day, there are between 8 and 22 nonstop flights that take off from Chicago Midway Airport and land in Orlando, with an average flight time of 2h 37m. The most common departure time is 5:00 am and most flights take off in the morning, while the most flights land at Orlando Airport. Each week, there are 109 flights. The most frequent day of departure is Saturday, when 20% of all weekly flights depart. The fewest flights depart on a Wednesday.

Which cabin class options are there for flights between Chicago Midway Airport and Orlando?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Chicago Midway Airport to Orlando take?

Direct flights take on average 2h 41m to travel the 982 miles between Chicago Midway Airport and Orlando.

What’s the earliest departure time from Chicago Midway Airport to Orlando?

Early birds can take the earliest flight from Chicago Midway Airport at 5:05 am and will be landing in Orlando at 9:00 am.

What’s the latest departure time from Chicago Midway Airport to Orlando?

If you prefer to fly at night, the latest flight from Chicago Midway Airport to Orlando jets off at 9:55 pm and lands at 1:30 am.

Good to know

Low season

September

High season

March

Cheapest flight

$34
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly with an average 38% 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 $34 for a one-way ticket and $84 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 Airbus A320neo is the aircraft model that flies most regularly on the Chicago Midway Airport to Orlando flight route.

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

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

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

    The two airlines most popular with KAYAK users for flights from Chicago to Orlando are Delta and Frontier. With an average price for the route of $486 and an overall rating of 8.0, Delta is the most popular choice. Frontier is also a great choice for the route, with an average price of $178 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.

See more FAQs

Top tips for finding a cheap flight from Chicago to Orlando

  • Looking for a cheap flight? 25% of our users found flights on this route for $59 or less one-way and $129 or less round-trip.

Prefer to fly non-stop from Chicago Midway Airport to Orlando?

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

Nonstop departures

Chicago Midway to Orlando

Monday

Frontier, Southwest

Frontier, Southwest

Tuesday

Frontier, Southwest

Frontier, Southwest

Wednesday

Frontier, Southwest

Frontier, Southwest

Thursday

Frontier, Southwest

Frontier, Southwest

Friday

Frontier, Southwest

Frontier, Southwest

Saturday

Frontier, Southwest

Frontier, Southwest

Sunday

Frontier, Southwest

Frontier, Southwest

See more direct flights

Nonstop returns

Orlando to Chicago Midway

Monday

Frontier, Southwest

Frontier, Southwest

Tuesday

Frontier, Southwest

Frontier, Southwest

Wednesday

Frontier, Southwest

Frontier, Southwest

Thursday

Frontier, Southwest

Frontier, Southwest

Friday

Frontier, Southwest

Frontier, Southwest

Saturday

Frontier, Southwest

Frontier, Southwest

Sunday

Frontier, Southwest

Frontier, Southwest

See more direct flights
See more direct flights

Top 4 airlines serving from Midway to Orlando

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 KAYAK reviews.
8.0
DeltaOverall score based on 11418 reviews
82boarding
80entertainment
79comfort
81overall
86crew
75food
Airline reviews

public website still broken for years randomly blocking browsers with privacy options active after loading a page maybe once. check-in on laptop was almost impossible but eventually randomly worked. had to print pass at airport since couldn't get back in to load digital pass on mobile firefox or chrome. red eye flight so smooth onboarding, plenty of room to spread out, easy offboarding. onboard wifi instructions mention vpn can cause problems connecting but fails to also mention private dns. no printed or built in menu list, seems weird to require personal device to point at qr code link for menu which does not even allow direct ordering. people with health condition risk related dietary restrictions trying to avoid for example cholesterol and sugar are left guessing what they can order either way without nutritional info highlights (cranberry juice was minute maid cocktail with as much suger as typical can of soda). tap to pay wasn't working and always seems sketchy to manually enter card info. good movie variety, so limited tv was okay.

Read more about Delta

public website still broken for years randomly blocking browsers with privacy options active after loading a page maybe once. check-in on laptop was almost impossible but eventually randomly worked. had to print pass at airport since couldn't get back in to load digital pass on mobile firefox or chrome. red eye flight so smooth onboarding, plenty of room to spread out, easy offboarding. onboard wifi instructions mention vpn can cause problems connecting but fails to also mention private dns. no printed or built in menu list, seems weird to require personal device to point at qr code link for menu which does not even allow direct ordering. people with health condition risk related dietary restrictions trying to avoid for example cholesterol and sugar are left guessing what they can order either way without nutritional info highlights (cranberry juice was minute maid cocktail with as much suger as typical can of soda). tap to pay wasn't working and always seems sketchy to manually enter card info. good movie variety, so limited tv was okay.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

Boarding super slow with people allowed to linger in aisles

There were choices for the snacks. Good choices and tasty lunch and breakfast as well.

First time travel in economy and the worst experience I ever had ! Shame on paying 600 dollars to be in a tuna can ! Service was terrible no even water no even class no even matters your flight attendants were lazy and sloppy very bad experience! After all these years traveling in first and once I try this cause I need to go to a destination for an emergency wow shame on you !

Everything was smooth and easy to fly. No complains and a lot of thanks!

More space in the cabin. The guy in front of me leaned his seat back and I felt he was sitting in my lap.

The boarding process was terrible especially with an indirect flight Chicago to Seattle to San Diego was terrible talking about we overbooked a flight idk if I’d take this airline ever again we got off our flight from Chicago to Seattle and we traveled for business and they told us our connecting flight was over booked and their was no seats asking people to take a delayed next flight and they don’t tell anyone coughing to wear masks seats 30A-B were terrible during the flight no one wants to sit next to people coughing all around I don’t want to be sick traveling for work or get sick anytime it’s very upsetting the staff doesn’t take this stuff serious to tell them to wear masks when they see people coughing and sneezing

We checked one bag. That was fast and the agent was fast and super nice. At the gate, boarding was fast and efficient. Flight was uneventful which was great because it was early in the morning and most folks were sleeping. Landing was great. Delta does a really good job of making the flying experience better all around considering you are sitting in such a small space on a plane for several hours. Flight from ALT to Panama City was short and uneventful as well. No entertainment but no need since it was such a short flight.

The announcements about boarding were unclear and har.d to understand I almost missed the flight even though I wa in the boarding area. .

Horrible. Flight was delayed and very bumpy. I was super unhappy

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

All the British airways staff were very helpful and friendly. Every thing was very smooth running from checking in boarding and arriving 40 minutes early. Which is a brilliant start to your holiday.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

The airplane was extremely hot the air conditioner wasn’t working I

My flight was cancelled and I am stranded in another state

Flight always gets delayed. Sat in the plane for over an hour before take off with no air con, still had to pay full price for snacks/drinks.

The airlines delay the flight 1 day and we refuse to take that option instead we need to take a bus ride, now we are expecting for refund the money, it was a horrible experience.

It would have been no e to have the option of a mid day flight and not super early or super late in the day.

Never made it to Atlanta due to the horrible policy of having to be at the gate 1 hour prior to departure. I was at the airport and the plane had not left Baltimore, but was not allowed to board.

Never got on the plane! My 2pm flight became 4am so I had to book southwest!

Well those seats! Man! On a short flight tolerable but too stiff and lack of cushioning make a longer flight uncomfortable. Good leg room tho, but I’m only 5’3”….

There was no WiFi available and trying to check baggage with the automated system never works with my Florida IDENTIFICATION

Passengers play their phones so everyone can hear them. No one tells them to use earbuds. Very annoying and unenjoyable.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

Everything was on time and smoothly run. All employees appeared happy and enjoying their job. The delay in take-off was unrelated to anything in Frontier’s control. I wish there were a caffeine-fee, sugar free soda drink option besides water. There are multiple zero sugar caffeine free options.

Everything was on time and smoothly run. All employees appeared happy and enjoying their job. The delay in take-off was unrelated to anything in Frontier’s control.

I like that the flight was not overcrowded, and I felt had space to spread out a little more. The flight was smooth for the most part no major turbulence. The crew was pretty good accommodating and professional.. the fellow passengers were cool as well… all good! Snacks always makes things better, but of course there were no snacks.

Be prepared for crowds and chaos upon arrival at the Orlando airport

Frontier is a mess. Kept changing flights and times on me. Ridiculous. Charged us twice for annual Discout Den membership.

Frontier system that tracts what you’ve paid for is horrible. I brought bags, tried to upgrade the weight of bag. Did it via the text service on their site. Got to the airport and they had no idea what was going on. Ended up paying way more than I was supposed to

The flights were right on time. The issue that was the most difficult was the lack of legroom on the planes

5 MINTUES LATE TO THEIR CHECK IN AND THEY WACK ME 200.00 BUCKS FOR RE BOOKING FEE AND PUT ME ON ANOTHER FLIGHT. @ THE BOARDING GATE IWATCH THEM BOARD MY ORIGINAL FLIGHT RIGHT IN FRONT OF ME- TOATL SCAM!

Flight was canceled both ways cost me a lot of time and money. Company takes advantage of people to make money, can’t call there is no phone number and in order to chat with an agent you have to know the secret way to get to a person rather than a robot. Never deal with them again.

Book cheap flights from Chicago to Orlando

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Orlando found on KAYAK in the last 72 hours.
4/9Tue
nonstopFrontier
2h 50mMDW-MCO
$34
5/18Sat
nonstopFrontier
2h 49mMDW-MCO
$39
4/11Thu
1 stop
7h 08mMDW-MCO
$73
5/25Sat
1 stopDelta
4h 57mMDW-MCO
$88
4/28Sun
2 stops
10h 41mMDW-MCO
$102
4/5Fri
1 stopAllegiant Air
9h 51mMDW-SFB
$113
4/5Fri
1 stopAllegiant Air
9h 51mMDW-SFB
$116
6/24Mon
1 stopDelta
5h 24mMDW-MCO
$120
4/10Wed
2 stopsPorter Airlines
11h 59mMDW-MCO
$367
8/7Wed
2 stopsPorter Airlines
10h 44mMDW-MCO
$502

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Last minute flights from Midway to Orlando

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Orlando that are departing in the next 10 days.
4/2Tue
nonstopFrontier
2h 59mMDW-MCO
4/4Thu
nonstopFrontier
3h 04mMCO-MDW
$103
4/2Tue
nonstopFrontier
2h 50mMDW-MCO
4/4Thu
nonstopFrontier
3h 04mMCO-MDW
$105
4/2Tue
nonstopFrontier
2h 59mMDW-MCO
4/9Tue
nonstopFrontier
3h 06mMCO-MDW
$110
4/1Mon
nonstopFrontier
2h 55mMDW-MCO
4/10Wed
multi-stopFrontier
7h 24mMCO-MDW
$118
4/1Mon
nonstop
2h 55mMDW-MCO
4/10Wed
multi-stop
8h 51mMCO-MDW
$142
3/29Fri
nonstop
2h 55mMDW-MCO
4/8Mon
multi-stop
15h 31mMCO-MDW
$223
3/29Fri
multi-stopDelta
4h 31mMDW-MCO
4/3Wed
multi-stopDelta
5h 34mMCO-MDW
$513
3/30Sat
multi-stopDelta
6h 21mMDW-MCO
4/5Fri
multi-stopDelta
4h 19mMCO-MDW
$545
3/29Fri
multi-stopAllegiant Air
11h 25mMDW-SFB
4/1Mon
multi-stopAllegiant Air
10h 25mSFB-MDW
$615
3/29Fri
multi-stopAllegiant Air
11h 25mMDW-SFB
3/31Sun
multi-stopAllegiant Air
31h 02mSFB-MDW
$628

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Chicago Midway Airport - Orlando Flights

Departure:

Chicago Midway Airport (MDW)United States

Cabin classes:

$67