$118+ Cheap flights from Midway (MDW) to Orlando Sanford Intl (SFB)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SFB
Nov 24 — Dec 11
Round-trip
1 adult, Economy
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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
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Cheapest flights from Midway to Orlando Sanford IntlExplore 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 25, 2026.
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 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/94:31 pm -
1 stop16h 36m
Thu 11/128:47 pm -
2 stops28h 00m
Deal found 10/22![Multiple Airlines logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/21:26 pm -
1 stop25h 59m
Fri 11/66:15 am -
2 stops14h 04m
Deal found 10/20![Allegiant Air logo]()
$294
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 11/94:31 pm -
1 stop16h 36m
Fri 11/136:15 am -
2 stops9h 11m
Deal found 10/24![Allegiant Air logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/164:31 pm -
1 stop16h 36m
Fri 11/207:00 am -
1 stop7h 40m
Deal found 10/21![Allegiant Air logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/94:31 pm -
1 stop16h 36m
Thu 11/127:57 pm -
1 stop19h 29m
Deal found 10/22![Allegiant Air logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 10/302:26 pm -
1 stop26h 57m
Sun 11/16:03 pm -
1 stop19h 33m
Deal found 10/20![Allegiant Air logo]()
$341
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/21:26 pm -
1 stop4h 51m
Thu 11/57:57 pm -
1 stop24h 22m
Deal found 10/21![Allegiant Air logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/68:09 pm -
1 stop21h 23m
Thu 11/127:57 pm -
1 stop19h 29m
Deal found 10/22![Allegiant Air logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/94:31 pm -
1 stop16h 36m
Sun 11/157:49 pm -
1 stop20h 52m
Deal found 10/22![Allegiant Air logo]()
$354
Best flights from Midway to Orlando Sanford IntlDiscover 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 October 25, 2026.
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 October 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 11/94:31 pm -
1 stop16h 36m
Fri 11/136:15 am -
2 stops9h 11m
Deal found 10/24![Allegiant Air logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/68:09 pm -
1 stop21h 23m
Thu 11/127:57 pm -
1 stop19h 29m
Deal found 10/22![Allegiant Air logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/94:31 pm -
1 stop16h 36m
Sun 11/157:49 pm -
1 stop20h 52m
Deal found 10/22![Allegiant Air logo]()
$354
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 -
1 stop21h 21m
Sun 11/157:49 pm -
1 stop20h 52m
Deal found 10/20![Allegiant Air logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 11/68:09 pm -
1 stop21h 23m
Mon 11/911:10 am -
1 stop5h 31m
Deal found 10/23![Allegiant Air logo]()
$396
This WAYA deal was found by Cheapflights users on 10/21. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/202:30 pm -
1 stop7h 37m
Sun 11/227:20 pm -
1 stop14h 19m
Deal found 10/21![Allegiant Air logo]()
$419
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/68:09 pm -
1 stop16h 28m
Sun 11/87:49 pm -
1 stop20h 52m
Deal found 10/22![Allegiant Air logo]()
$437
Last-minute flights from Midway to Orlando Sanford IntlDiscover last-minute flight deals from Midway to Orlando Sanford Intl. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Orlando Sanford Intl. Data last updated October 25, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 10/302:26 pm -
1 stop26h 57m
Sun 11/16:03 pm -
1 stop19h 33m
Deal found 10/20![Allegiant Air logo]()
$341
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/21:26 pm -
1 stop25h 59m
Fri 11/66:15 am -
2 stops14h 04m
Deal found 10/20![Allegiant Air logo]()
$294
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/21:26 pm -
1 stop4h 51m
Thu 11/57:57 pm -
1 stop24h 22m
Deal found 10/21![Allegiant Air logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/68:09 pm -
1 stop21h 23m
Thu 11/127:57 pm -
1 stop19h 29m
Deal found 10/22![Allegiant Air logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/94:31 pm -
1 stop16h 36m
Thu 11/128:47 pm -
2 stops28h 00m
Deal found 10/22![Multiple Airlines logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 11/94:31 pm -
1 stop16h 36m
Fri 11/136:15 am -
2 stops9h 11m
Deal found 10/24![Allegiant Air logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/94:31 pm -
1 stop16h 36m
Thu 11/127:57 pm -
1 stop19h 29m
Deal found 10/22![Allegiant Air logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/94:31 pm -
1 stop16h 36m
Sun 11/157:49 pm -
1 stop20h 52m
Deal found 10/22![Allegiant Air logo]()
$354
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/164:31 pm -
1 stop16h 36m
Fri 11/207:00 am -
1 stop7h 40m
Deal found 10/21![Allegiant Air logo]()
$303
One-way flights from Midway to Orlando Sanford IntlSearch for one-way flight options from Midway to Orlando Sanford Intl. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
Search for one-way flight options from Midway to Orlando Sanford Intl. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 11/94:31 pm -
1 stop16h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Allegiant Air logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 10/302:26 pm -
1 stop26h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Allegiant Air logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/164:31 pm -
1 stop16h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Allegiant Air logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 -
1 stop26h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Allegiant Air logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/21:26 pm -
1 stop25h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Allegiant Air logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 10/22. 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.
Sat 12/512:28 pm -
2 stops21h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/239:29 am -
1 stop21h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Allegiant Air logo]()
$155
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 October 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $292 (Kiwi.com) |
One-way from | $118 (Kiwi.com) |
Popular in | June |
Cheapest in | February |
Average price | $315 |
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 7,457,451 searches. Data last updated October 25, 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
Cheapest round-trip
ChicagoOrlando
MDW Chicago Midway - SFB Orlando Sanford Intl
MDWSFB
Chicago Midway
Fri 10/30
2:26 pm-6:23 pm
1 stop26h 57m
Orlando Sanford Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$125
ChicagoOrlando
MDW Chicago Midway - SFB Orlando Sanford Intl
MDWSFB
Chicago Midway
Wed 1/6
5:21 pm-10:10 am
2 stops39h 49m
Orlando Sanford Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$184
ChicagoOrlando
MDW Chicago Midway - SFB Orlando Sanford Intl
MDWSFB
Chicago Midway
Thu 11/19
6:08 am-6:19 pm
3 stops59h 11m
Orlando Sanford Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$222
ChicagoOrlando
MDW Chicago Midway - SFB Orlando Sanford Intl
MDWSFB
Chicago Midway
Wed 2/3
1:18 pm-5:13 pm
3 stops26h 55m
Orlando Sanford Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$230
ChicagoOrlando
MDW Chicago Midway - SFB Orlando Sanford Intl
MDWSFB
Chicago Midway
Thu 12/17
6:52 am-11:03 pm
3 stops39h 11m
Orlando Sanford Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$233
ChicagoOrlando
MDW Chicago Midway - SFB Orlando Sanford Intl
MDWSFB
Chicago Midway
Fri 11/13
6:08 am-10:33 am
3 stops27h 25m
Orlando Sanford Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$243
ChicagoOrlando
MDW Chicago Midway - SFB Orlando Sanford Intl
MDWSFB
Chicago Midway
Thu 11/19
9:44 am-5:08 pm
2 stops30h 24m
Orlando Sanford Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$249
ChicagoOrlando
MDW Chicago Midway - SFB Orlando Sanford Intl
MDWSFB
Chicago Midway
Sat 10/31
7:25 am-10:47 pm
3 stops38h 22m
Orlando Sanford Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$251
ChicagoOrlando
MDW Chicago Midway - SFB Orlando Sanford Intl
MDWSFB
Chicago Midway
Mon 12/21
1:11 pm-6:32 pm
3 stops28h 21m
Orlando Sanford Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$252
Quickest round-trip
ChicagoOrlando
MDW Chicago Midway - SFB Orlando Sanford Intl
MDWSFB
Chicago Midway
Thu 12/17
9:41 am-8:17 pm
2 stops9h 36m
Orlando Sanford Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$255
Showing 1-10 of 17 resultsSorted by cheapest first
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.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
MDW-SFB
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.
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.
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