MDW - MCO

$95 Find Cheap Flights from Chicago Midway Airport to Orlando Airport - Compare and Save

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 10/26. 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

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Everything you should know

Cheapest round-trip
$194
Typical prices: $170-$339
Frontier
Wed 10/21Tue 10/27
MDW - MCO • 1 stop
Cheapest non-stop
$237
Typical prices: $247-$412
Southwest
Thu 8/13Mon 8/17
MDW - MCO • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Frontier Economy Bundle adds a carry-on and no change fees for budget flyers.
Southwest Rapid Rewards has no blackout dates; Midway often means shorter security lines.
Expert advice
Expert advice
Expert advice
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Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 36m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Southwest
Most punctual • 83% on-time
Night flights
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cincinnati (CVG)
Cheapest • Avg $165 (round-trip)
Cincinnati (CVG)
Shortest trip • 5h 15m (one-way)
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 37% price drop
March
Most popular
Good to know
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+1
+1
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Good to know
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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

Wed, Oct 21 - Tue, Oct 27
Frontier Logo
6:40 am - 2:37 pm
MDW
-
MCO
6h 57m
1 stop
Frontier Logo
5:29 pm - 9:53 pm
MCO
-
MDW
5h 24m
1 stop
$194Frontier
Thu, Oct 22 - Tue, Oct 27
Frontier Logo
6:40 am - 2:37 pm
MDW
-
MCO
6h 57m
1 stop
Frontier Logo
5:29 pm - 9:53 pm
MCO
-
MDW
5h 24m
1 stop
$207Frontier
Tue, Aug 18 - Tue, Aug 25
Frontier Logo
11:50 am - 6:33 pm
MDW
-
MCO
5h 43m
1 stop
Frontier Logo
5:23 pm - 10:47 pm
MCO
-
MDW
6h 24m
1 stop
$208Frontier
Wed, Aug 5 - Tue, Aug 18
Frontier Logo
6:05 am - 6:33 pm
MDW
-
MCO
11h 28m
1 stop
Frontier Logo
5:23 pm - 10:47 pm
MCO
-
MDW
6h 24m
1 stop
$210Frontier
Thu, Oct 22 - Tue, Oct 27
Frontier Logo
6:40 am - 2:37 pm
MDW
-
MCO
6h 57m
1 stop
Frontier Logo
5:29 pm - 9:53 pm
MCO
-
MDW
5h 24m
1 stop
$211Frontier
Tue, Nov 10 - Sat, Nov 14
Frontier Logo
7:25 am - 5:21 pm
MDW
-
MCO
8h 56m
1 stop
Frontier Logo
5:29 pm - 9:53 pm
MCO
-
MDW
5h 24m
1 stop
$213Frontier
Thu, Aug 13 - Mon, Aug 17
Multiple Airlines Logo
11:06 am - 7:57 pm
MDW
-
MCO
7h 51m
1 stop
Multiple Airlines Logo
10:29 am - 2:59 pm
MCO
-
MDW
5h 30m
1 stop
$215Multiple Airlines
Thu, Aug 13 - Mon, Aug 17
Multiple Airlines Logo
11:06 am - 7:57 pm
MDW
-
MCO
7h 51m
1 stop
Multiple Airlines Logo
10:29 am - 2:59 pm
MCO
-
MDW
5h 30m
1 stop
$216Multiple Airlines
Mon, Aug 10 - Mon, Aug 17
Multiple Airlines Logo
6:05 am - 2:23 pm
MDW
-
MCO
7h 18m
1 stop
Multiple Airlines Logo
10:29 am - 2:59 pm
MCO
-
MDW
5h 30m
1 stop
$217Multiple Airlines
Sat, Aug 15 - Mon, Aug 17
Multiple Airlines Logo
11:06 am - 7:57 pm
MDW
-
MCO
7h 51m
1 stop
Multiple Airlines Logo
10:29 am - 2:59 pm
MCO
-
MDW
5h 30m
1 stop
$218Multiple 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 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 October.

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, Sunday 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 January, where tickets cost $197 (return) on average. On the other hand, the most expensive months are June and July, where the average cost of round-trip tickets is $467 and $461 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 $382, 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.

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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.

Read more
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.

Read more

Good to know

Low season

August

Cheapest flight

$95
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 7% 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 5 days, the lowest price for a flight from Chicago Midway Airport to Orlando Airport was $104 for a one-way ticket and $208 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, JetBlue, 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 $418 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 $200 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 $172 or less one-way and $318 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

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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

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
Southwest flights from Chicago Midway Airport to Orlando Airport