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Orlando Sanford Intl

$107+ 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 7/24. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SFB
Jul 10 — Jul 171
Fri 7/10
Fri 7/17
1 adult, Economy
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Cheap 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 June 10, 2026.

This Kiwi.com deal was found by Cheapflights users on 6/6. 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.
Thu 7/92:48 pm
MDW
-
SFB
1 stop25h 33m
Allegiant Air
Sun 7/128:58 pm
SFB
-
MDW
1 stop18h 40m
Allegiant Air
Deal found 6/6$214
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 6/296:38 pm
MDW
-
SFB
1 stop16h 14m
Allegiant Air
Wed 7/84:48 pm
SFB
-
MDW
1 stop22h 10m
Allegiant Air
Deal found 6/7$238
This Kiwi.com deal was found by Cheapflights users on 6/9. 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 7/313:28 pm
MDW
-
SFB
1 stop7h 07m
Allegiant Air
Wed 8/54:50 pm
SFB
-
MDW
1 stop22h 09m
Allegiant Air
Deal found 6/9$250
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Sun 8/22:48 pm
MDW
-
SFB
1 stop4h 41m
Allegiant Air
Sun 8/99:20 pm
SFB
-
MDW
1 stop18h 39m
Allegiant Air
Deal found 6/9$253
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/103:28 pm
MDW
-
SFB
1 stop7h 07m
Allegiant Air
Sun 7/128:58 pm
SFB
-
MDW
1 stop18h 40m
Allegiant Air
Deal found 6/8$278
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 6/158:20 pm
MDW
-
SFB
1 stop14h 32m
Allegiant Air
Sun 7/128:58 pm
SFB
-
MDW
1 stop18h 40m
Allegiant Air
Deal found 6/5$287
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 6/158:20 pm
MDW
-
SFB
1 stop14h 32m
Allegiant Air
Sun 6/218:56 pm
SFB
-
MDW
1 stop23h 34m
Allegiant Air
Deal found 6/5$294
This Kiwi.com deal was found by Cheapflights users on 6/7. 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.
Thu 7/302:48 pm
MDW
-
SFB
2 stops24h 53m
Allegiant Air
Thu 8/69:20 pm
SFB
-
MDW
1 stop18h 39m
Allegiant Air
Deal found 6/7$296
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 7/103:28 pm
MDW
-
SFB
1 stop7h 07m
Allegiant Air
Sat 7/188:24 pm
SFB
-
MDW
1 stop18h 34m
Allegiant Air
Deal found 6/7$302
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 11/133:16 pm
MDW
-
SFB
1 stop26h 16m
Allegiant Air
Fri 11/207:00 am
SFB
-
MDW
1 stop7h 40m
Allegiant Air
Deal found 6/5$311
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Sun 7/262:48 pm
MDW
-
SFB
1 stop4h 41m
Allegiant Air
Sun 8/28:58 pm
SFB
-
MDW
1 stop18h 40m
Allegiant Air
Deal found 6/10$316
This Kiwi.com deal was found by Cheapflights users on 6/9. 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 7/313:28 pm
MDW
-
SFB
1 stop7h 07m
Multiple Airlines
Wed 8/56:15 pm
SFB
-
MDW
2 stops28h 48m
Multiple Airlines
Deal found 6/9$320

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 June 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$214
(Kiwi.com)

One-way from

$107
(Kiwi.com)

Popular in

June

Cheapest in

August

Average price

$330
Provider with most accurate pricing for Chicago Midway-Orlando Sanford Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Orlando Sanford Intl flights.
Search Deals
From Chicago Midway to Orlando Sanford Intl
Search Deals
One-way flight from Chicago Midway to Orlando Sanford Intl
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($29 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals

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 June 10, 2026.
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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Mon 6/29

6:38 pm-11:52 am

1 stop16h 14m

Orlando Sanford Intl

Wed 7/8

4:48 pm-1:58 pm

1 stop22h 10m

$238

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Fri 7/31

3:28 pm-11:35 pm

1 stop7h 07m

Orlando Sanford Intl

Wed 8/5

4:50 pm-1:59 pm

1 stop22h 09m

$250

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Fri 7/10

3:28 pm-11:35 pm

1 stop7h 07m

Orlando Sanford Intl

Sun 7/12

8:58 pm-2:38 pm

1 stop18h 40m

$278

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Thu 7/30

2:48 pm-4:41 pm

2 stops24h 53m

Orlando Sanford Intl

Thu 8/6

9:20 pm-2:59 pm

1 stop18h 39m

$296

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Fri 7/10

3:28 pm-11:35 pm

1 stop7h 07m

Orlando Sanford Intl

Sat 7/18

8:24 pm-1:58 pm

1 stop18h 34m

$302

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Fri 11/13

3:16 pm-6:32 pm

1 stop26h 16m

Orlando Sanford Intl

Fri 11/20

7:00 am-1:40 pm

1 stop7h 40m

$311
Quickest round-trip

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Sun 7/26

2:48 pm-8:29 pm

1 stop4h 41m

Orlando Sanford Intl

Sun 8/2

8:58 pm-2:38 pm

1 stop18h 40m

$316

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Sun 8/9

2:49 pm-3:11 pm

1 stop23h 22m

Orlando Sanford Intl

Fri 8/14

6:40 pm-8:24 am

2 stops38h 44m

$328

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Sun 7/19

2:48 pm-8:29 pm

1 stop4h 41m

Orlando Sanford Intl

Sun 7/26

8:58 pm-2:38 pm

1 stop18h 40m

$331

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Sun 7/5

2:48 pm-8:29 pm

1 stop4h 41m

Orlando Sanford Intl

Sun 7/12

8:58 pm-2:38 pm

1 stop18h 40m

$356

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

Showing 1-10 of 22 resultsSorted by cheapest first
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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 June.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*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 FlightHub the most. FlightHub 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

How often are flights from Chicago to Orlando delayed?

About 100% of weekly flights between Chicago and Orlando have experienced delays in the past year, with the average delay time being 57 minutes.

What is the most punctual flight time for Chicago to Orlando flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Thursday has historically faced a higher average of delays compared to other days of the week.

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 14m. 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

See prices for flight routes from nearby airports that may be better suited for you.
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