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Orlando Sanford Intl

$131+ Cheap flights from Midway (MDW) to Orlando Sanford Intl (SFB)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SFB
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Midway to Orlando Sanford Intl

Best flights from Midway to Orlando Sanford Intl
Discover carefully curated flight deals from Midway to Orlando Sanford Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:20 pmMDW - SFB
1 stop16h 33mAllegiant Air
Sun 6/148:55 pmSFB - MDW
1 stop23h 35mAllegiant Air
Deal found 12/11$370

Find flight deals from Midway to Orlando Sanford Intl

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Orlando Sanford Intl (SFB). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 12, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$370
(Kiwi.com)

One-way from

$131
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$314
Provider with most accurate pricing for Chicago Midway-Orlando Sanford Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Orlando Sanford Intl flights.
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From Chicago Midway to Orlando Sanford Intl
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One-way flight from Chicago Midway to Orlando Sanford Intl
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Highest demand for flights based on searches. 10% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Orlando Sanford Intl that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 12, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Orlando Sanford Intl Airport that are best for you.

Fly from

Midway

Fly to

Orlando Sanford Intl

Route

Depart

Return

Price

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Fri 6/5

8:20 pm-1:53 pm

1 stop16h 33m

Orlando Sanford Intl

Sun 6/14

8:55 pm-7:30 pm

1 stop23h 35m

$370

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Sun 1/25

5:01 pm-7:59 pm

2 stops25h 58m

$131

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Sun 2/22

6:00 am-10:57 am

2 stops27h 57m

$158

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Sun 1/18

9:13 am-11:13 am

2 stops25h 00m

$159

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Fri 2/20

7:53 pm-8:46 pm

3 stops47h 53m

$171

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Wed 12/31

6:12 am-8:31 am

3 stops49h 19m

$192

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Tue 12/30

7:44 am-10:50 pm

2 stops38h 06m

$200

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Sun 2/1

10:17 am-7:40 am

2 stops20h 23m

$215

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Sat 12/20

6:12 am-5:28 pm

3 stops34h 16m

$219

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Thu 1/1

6:33 pm-4:08 pm

3 stops44h 35m

$222

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 11 results
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Compare providers for flights from Midway to Orlando Sanford Intl

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Orlando Sanford Intl in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Orlando Sanford Intl Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Orlando Sanford Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Orlando Sanford Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Orlando Sanford Intl Airport flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Orlando Sanford Intl Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to Orlando Sanford Intl

Have a flexible travel schedule? Discover the best time to fly to Orlando Sanford Intl from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Orlando Sanford Intl Airport

What is the cheapest time of day to fly from MDW to SFB?

Find hourly flight availability from Midway to Orlando Sanford Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 12, 2025.

It’s typically best to fly out from Chicago Midway Airport to Orlando Sanford Intl Airport in the morning. Doing so could potentially save you 39% on the flight price compared to flying in the evening, which is usually more expensive.

Related info for your journey

Find useful and relevant information for your journey from Midway to Orlando Sanford Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago Midway Airport to Orlando Sanford Intl Airport?

    Airlines like Allegiant Air fly from Chicago Midway Airport to Orlando Sanford Intl Airport in about 16h 33m. The time it takes to get you to your destination can typically vary by up to . Airlines will cover a distance of 969 mi.

  • Can I find deals for flights from Midway to Orlando Sanford Intl that include hotel bookings?

    Yes. In addition to deals on Midway to Orlando Sanford Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Orlando Sanford Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Orlando Sanford Intl.

  • Can I find deals for business class flights from Midway to Orlando Sanford Intl?

    Yes. Cheapflights offers flight deals from Midway to Orlando Sanford Intl by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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