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Orlando Sanford Intl

$115+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SFB
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Cheap 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 October 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$231
(Mytrip)

One-way from

$115
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$227
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. 6% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Midway to Orlando Sanford Intl

Cheapest flights from Midway to Orlando Sanford Intl
Explore the most affordable flight options available from Midway to Orlando Sanford Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 28, 2025.

This Mytrip deal was found by Cheapflights users on 10/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/104:12 pmMDW - SFB
1 stop5h 51mAllegiant Air
Fri 11/147:50 amSFB - MDW
1 stop9h 55mAllegiant Air
Deal found 10/26$234
This Mytrip deal was found by Cheapflights users on 10/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/72:57 pmMDW - SFB
1 stop6h 59mAllegiant Air
Sun 11/99:55 pmSFB - MDW
1 stop15h 07mAllegiant Air
Deal found 10/27$265
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 11/217:36 pmMDW - SFB
1 stop20h 10mAllegiant Air
Mon 11/248:53 amSFB - MDW
1 stop5h 28mAllegiant Air
Deal found 10/26$277
This Mytrip deal was found by Cheapflights users on 10/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/317:06 pmMDW - SFB
1 stop14h 30mAllegiant Air
Mon 11/310:48 amSFB - MDW
1 stop6h 49mAllegiant Air
Deal found 10/26$301
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/217:36 pmMDW - SFB
1 stop20h 10mMultiple Airlines
Mon 11/246:25 pmSFB - MDW
2 stops18h 17mMultiple Airlines
Deal found 10/27$320
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 10/315:52 pmMDW - SFB
1 stop21h 14mAllegiant Air
Sun 11/29:56 pmSFB - MDW
1 stop19h 41mAllegiant Air
Deal found 10/27$324
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Mon 11/104:12 pmMDW - SFB
1 stop5h 51mMultiple Airlines
Fri 11/148:00 amSFB - MDW
2 stops9h 57mMultiple Airlines
Deal found 10/26$354
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Mon 10/275:54 pmMDW - SFB
1 stop26h 07mAllegiant Air
Mon 11/310:48 amSFB - MDW
1 stop6h 49mAllegiant Air
Deal found 10/26$360

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 October 28, 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

Mon 11/10

4:12 pm-11:03 pm

1 stop5h 51m

Orlando Sanford Intl

Fri 11/14

7:50 am-4:45 pm

1 stop9h 55m

$234

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Fri 11/7

2:57 pm-10:56 pm

1 stop6h 59m

Orlando Sanford Intl

Sun 11/9

9:55 pm-12:02 pm

1 stop15h 07m

$265

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Fri 11/21

7:36 pm-4:46 pm

1 stop20h 10m

Orlando Sanford Intl

Mon 11/24

8:53 am-1:21 pm

1 stop5h 28m

$308

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Fri 11/21

7:36 pm-4:46 pm

1 stop20h 10m

Orlando Sanford Intl

Mon 11/24

6:25 pm-11:42 am

2 stops18h 17m

$320

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Mon 11/10

12:52 pm-6:23 pm

1 stop4h 31m

Orlando Sanford Intl

Thu 11/13

9:55 pm-4:45 pm

1 stop19h 50m

$324

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Mon 11/10

4:12 pm-11:03 pm

1 stop5h 51m

Orlando Sanford Intl

Fri 11/14

8:00 am-4:57 pm

2 stops9h 57m

$354

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Wed 11/26

2:11 pm-9:05 pm

1 stop5h 54m

Orlando Sanford Intl

Sat 11/29

9:54 pm-2:24 pm

1 stop17h 30m

$582

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Tue 11/25

6:20 am-7:32 pm

2 stops36h 12m

Orlando Sanford Intl

Sun 11/30

10:53 am-3:34 pm

1 stop5h 41m

$703

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Wed 11/26

7:44 pm-12:00 pm

1 stop15h 16m

Orlando Sanford Intl

Sun 11/30

10:53 am-3:34 pm

1 stop5h 41m

$721

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Thu 11/27

6:20 am-3:35 pm

2 stops32h 15m

Orlando Sanford Intl

Sun 11/30

10:53 am-3:34 pm

1 stop5h 41m

$733

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 21 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 October.
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 October 28, 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 5h 51m. 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.

See more FAQs

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Alternative routes for Midway to Orlando Sanford Intl

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