HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Orlando Sanford Intl

$112+ 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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SFB
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Orlando Sanford Intl with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 September 11, 2025.

Round-trip from

$231
(Kiwi.com)

One-way from

$113
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$190
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. 7% potential increase in price ($20 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 September 2025
Search Deals

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 September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Mon 10/278:24 pmMDW - SFB
1 stop20h 03mAllegiant Air
Mon 11/310:48 amSFB - MDW
1 stop6h 49mAllegiant Air
Deal found 9/10$231
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Mon 9/2212:50 pmMDW - SFB
1 stop7h 16mAllegiant Air
Fri 9/261:48 pmSFB - MDW
1 stop6h 12mAllegiant Air
Deal found 9/10$264
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 11/72:57 pmMDW - SFB
1 stop6h 59mAllegiant Air
Sun 11/99:55 pmSFB - MDW
1 stop15h 07mAllegiant Air
Deal found 9/9$283
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 11/212:11 pmMDW - SFB
1 stop7h 57mAllegiant Air
Sun 11/238:44 pmSFB - MDW
1 stop23h 02mAllegiant Air
Deal found 9/9$296
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Wed 9/179:00 amMDW - SFB
2 stops7h 45mMultiple Airlines
Sun 9/219:58 pmSFB - MDW
1 stop15h 02mMultiple Airlines
Deal found 9/11$308
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 11/217:36 pmMDW - SFB
1 stop20h 10mAllegiant Air
Tue 11/257:46 pmSFB - MDW
1 stop18h 35mAllegiant Air
Deal found 9/8$322
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Thu 10/98:25 amMDW - SFB
2 stops10h 50mMultiple Airlines
Thu 10/169:51 pmSFB - MDW
1 stop19h 43mMultiple Airlines
Deal found 9/9$335
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Thu 10/239:26 pmMDW - SFB
2 stops15h 49mMultiple Airlines
Sun 10/269:51 pmSFB - MDW
1 stop20h 13mMultiple Airlines
Deal found 9/9$346
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 9/127:50 pmMDW - SFB
1 stop21h 43mAllegiant Air
Sun 9/149:58 pmSFB - MDW
1 stop15h 02mAllegiant Air
Deal found 9/8$390
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Fri 11/217:36 pmMDW - SFB
1 stop20h 10mAllegiant Air
Sat 11/297:57 pmSFB - MDW
1 stop20h 37mAllegiant Air
Deal found 9/10$463

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 September 11, 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 10/27

8:24 pm-5:27 pm

1 stop20h 03m

Orlando Sanford Intl

Mon 11/3

10:48 am-4:37 pm

1 stop6h 49m

$231

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Mon 9/22

12:50 pm-9:06 pm

1 stop7h 16m

Orlando Sanford Intl

Fri 9/26

1:48 pm-7:00 pm

1 stop6h 12m

$264

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

$283

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Fri 11/21

2:11 pm-11:08 pm

1 stop7h 57m

Orlando Sanford Intl

Sun 11/23

8:44 pm-6:46 pm

1 stop23h 02m

$296

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Wed 9/17

9:00 am-5:45 pm

2 stops7h 45m

Orlando Sanford Intl

Sun 9/21

9:58 pm-12:00 pm

1 stop15h 02m

$308

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Fri 11/21

7:36 pm-4:46 pm

1 stop20h 10m

Orlando Sanford Intl

Tue 11/25

7:46 pm-1:21 pm

1 stop18h 35m

$322

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Thu 10/9

8:25 am-8:15 pm

2 stops10h 50m

Orlando Sanford Intl

Thu 10/16

9:51 pm-4:34 pm

1 stop19h 43m

$335

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Thu 10/23

9:26 pm-2:15 pm

2 stops15h 49m

Orlando Sanford Intl

Sun 10/26

9:51 pm-5:04 pm

1 stop20h 13m

$346

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Fri 11/21

7:36 pm-4:46 pm

1 stop20h 10m

Orlando Sanford Intl

Sat 11/29

7:57 pm-3:34 pm

1 stop20h 37m

$463

ChicagoOrlando

MDW - SFB

MDWSFB

Chicago Midway

Fri 9/26

7:50 pm-10:40 pm

1 stop25h 50m

$112

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 15 results
1
2

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 September 11, 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 40% 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 20h 03m. 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.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Orlando Sanford Intl Airport?

    Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Orlando Sanford Intl Airport (average of $137). Flying from Chicago Midway Airport to Orlando Sanford Intl Airport in March is currently the most expensive (average of $231). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Orlando Sanford Intl

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Orlando flights
Midway to Orlando flights
Rockford to Orlando Sanford Intl flights
O'Hare Intl to Orlando Sanford Intl flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.