$99+ Cheap flights from Sarasota (SRQ) to Midway (MDW)
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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
SRQ — MDW
Nov 9 — Nov 161
Round-trip
1 adult, Economy
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Find cheap flights from Sarasota to Midway 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 Sarasota to Midway
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Cheapest flights from Sarasota to MidwayExplore the most affordable flight options available from Sarasota to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 10, 2026.
Explore the most affordable flight options available from Sarasota to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 10, 2026.
This Southwest deal was found by Cheapflights users on 10/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/412:45 pm -
Nonstop3h 00m
Sat 11/73:45 pm -
Nonstop2h 40m
Deal found 10/7![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 10/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:40 am -
1 stop4h 50m
Mon 11/26:50 pm -
Nonstop2h 35m
Deal found 10/6![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 10/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:30 pm -
Nonstop2h 45m
Wed 11/411:30 am -
1 stop9h 00m
Deal found 10/8![Southwest logo]()
$262
This Southwest deal was found by Cheapflights users on 10/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:40 am -
1 stop4h 50m
Tue 11/38:50 am -
1 stop6h 40m
Deal found 10/8![Southwest logo]()
$265
This Southwest deal was found by Cheapflights users on 10/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/711:55 am -
1 stop6h 10m
Thu 11/127:30 am -
1 stop5h 55m
Deal found 10/8![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 10/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/242:40 pm -
1 stop4h 20m
Wed 11/259:50 am -
1 stop7h 50m
Deal found 10/8![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 10/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:40 pm -
1 stop4h 35m
Sat 10/316:05 am -
2 stops9h 25m
Deal found 10/7![Southwest logo]()
$270
This Southwest deal was found by Cheapflights users on 10/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:20 am -
Nonstop2h 45m
Tue 11/108:50 am -
1 stop6h 40m
Deal found 10/5![Southwest logo]()
$272
Best flights from Sarasota to MidwayDiscover carefully curated flight deals from Sarasota to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 10, 2026.
Discover carefully curated flight deals from Sarasota to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 10, 2026.
This Southwest deal was found by Cheapflights users on 10/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:05 am -
1 stop5h 25m
Tue 11/103:00 pm -
1 stop5h 55m
Deal found 10/6![Southwest logo]()
$265
This Delta deal was found by Cheapflights users on 10/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2611:16 am -
1 stop12h 38m
Wed 12/26:00 am -
1 stop6h 23m
Deal found 10/5![Delta logo]()
$338
This Southwest deal was found by Cheapflights users on 10/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:30 pm -
Nonstop2h 45m
Sun 11/85:15 am -
1 stop7h 30m
Deal found 10/8![Southwest logo]()
$354
This Delta deal was found by Cheapflights users on 10/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:00 am -
1 stop5h 43m
Sun 11/86:04 am -
1 stop5h 12m
Deal found 10/5![Delta logo]()
$436
This Southwest deal was found by Cheapflights users on 10/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:00 am -
2 stops8h 55m
Thu 11/51:20 pm -
2 stops7h 35m
Deal found 10/7![Southwest logo]()
$407
This Southwest deal was found by Cheapflights users on 10/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:50 pm -
2 stops7h 20m
Sun 11/86:50 pm -
Nonstop2h 40m
Deal found 10/5![Southwest logo]()
$415
This Delta deal was found by Cheapflights users on 10/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/245:52 pm -
1 stop5h 30m
Tue 12/296:00 am -
1 stop7h 36m
Deal found 10/6![Delta logo]()
$492
This Southwest deal was found by Cheapflights users on 10/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:55 am -
2 stops8h 50m
Wed 11/254:20 pm -
2 stops7h 00m
Deal found 10/8![Southwest logo]()
$421
This Southwest deal was found by Cheapflights users on 10/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/242:05 pm -
1 stop5h 00m
Sun 10/258:15 pm -
Nonstop2h 40m
Deal found 10/5![Southwest logo]()
$489
This Southwest deal was found by Cheapflights users on 10/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:15 am -
2 stops6h 10m
Fri 10/237:05 am -
1 stop5h 05m
Deal found 10/9![Southwest logo]()
$504
This Southwest deal was found by Cheapflights users on 10/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/133:05 pm -
Nonstop2h 50m
Thu 10/158:10 am -
Nonstop2h 40m
Deal found 10/9![Southwest logo]()
$515
Last-minute flights from Sarasota to MidwayDiscover last-minute flight deals from Sarasota to Midway. Data last updated October 10, 2026 and is based on user searches.
Discover last-minute flight deals from Sarasota to Midway. Data last updated October 10, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:40 pm -
1 stop4h 35m
Sat 10/316:05 am -
2 stops9h 25m
Deal found 10/7![Southwest logo]()
$270
This Southwest deal was found by Cheapflights users on 10/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:40 am -
1 stop4h 50m
Mon 11/26:50 pm -
Nonstop2h 35m
Deal found 10/6![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 10/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:40 am -
1 stop4h 50m
Tue 11/38:50 am -
1 stop6h 40m
Deal found 10/8![Southwest logo]()
$265
This Southwest deal was found by Cheapflights users on 10/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:30 pm -
Nonstop2h 45m
Wed 11/411:30 am -
1 stop9h 00m
Deal found 10/8![Southwest logo]()
$262
This Southwest deal was found by Cheapflights users on 10/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/412:45 pm -
Nonstop3h 00m
Sat 11/73:45 pm -
Nonstop2h 40m
Deal found 10/7![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 10/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:20 am -
Nonstop2h 45m
Tue 11/108:50 am -
1 stop6h 40m
Deal found 10/5![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 10/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/711:55 am -
1 stop6h 10m
Thu 11/127:30 am -
1 stop5h 55m
Deal found 10/8![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 10/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/242:40 pm -
1 stop4h 20m
Wed 11/259:50 am -
1 stop7h 50m
Deal found 10/8![Southwest logo]()
$267
One-way flights from Sarasota to MidwaySearch for one-way flight options from Sarasota to Midway. Find affordable one-way fares based on user searches. Data last updated October 10, 2026.
Search for one-way flight options from Sarasota to Midway. Find affordable one-way fares based on user searches. Data last updated October 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/9. 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 11/1211:16 am -
1 stop28h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Allegiant Air logo]()
$99
This Southwest deal was found by Cheapflights users on 10/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/311:00 pm -
Nonstop2h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Southwest logo]()
$123
This Southwest deal was found by Cheapflights users on 10/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:30 pm -
Nonstop2h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Southwest logo]()
$124
This Southwest deal was found by Cheapflights users on 10/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/242:40 pm -
1 stop4h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Southwest logo]()
$128
This Southwest deal was found by Cheapflights users on 10/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/74:00 pm -
1 stop4h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Southwest logo]()
$133
This Southwest deal was found by Cheapflights users on 10/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:45 pm -
1 stop5h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Southwest logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 12/47:00 am -
2 stops29h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 10/7. 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 11/67:30 am -
2 stops35h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$150
This Delta deal was found by Cheapflights users on 10/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:24 pm -
1 stop5h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Delta logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 10/9. 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 12/107:30 am -
2 stops32h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$153
Find flight deals from Sarasota to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Sarasota (SRQ) to Midway (MDW). 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 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $245 (Southwest) |
One-way from | $99 (Kiwi.com) |
Popular in | November |
Cheapest in | May |
Average price | $413 |
Good round-trip deal | $413 or less |
Good one-way deal | $208 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Sarasota to Midway 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 10, 2026.
Use the filters below to find and compare flights from Sarasota to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
SarasotaChicago
SRQ Sarasota Bradenton Intl - MDW Chicago Midway
SRQMDW
Sarasota Bradenton Intl
Sat 12/5
3:15 pm-5:00 pm
Nonstop2h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$123
SarasotaChicago
SRQ Sarasota Bradenton Intl - MDW Chicago Midway
SRQMDW
Sarasota Bradenton Intl
Sat 12/12
6:00 am-10:28 am
1 stop5h 28m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$133
SarasotaChicago
SRQ Sarasota Bradenton Intl - MDW Chicago Midway
SRQMDW
Sarasota Bradenton Intl
Tue 12/8
6:00 am-10:28 am
1 stop5h 28m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$133
SarasotaChicago
SRQ Sarasota Bradenton Intl - MDW Chicago Midway
SRQMDW
Sarasota Bradenton Intl
Mon 12/7
4:38 pm-10:54 pm
1 stop7h 16m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$134
SarasotaChicago
SRQ Sarasota Bradenton Intl - MDW Chicago Midway
SRQMDW
Sarasota Bradenton Intl
Wed 12/23
6:25 pm-8:10 pm
Nonstop2h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
SarasotaChicago
SRQ Sarasota Bradenton Intl - MDW Chicago Midway
SRQMDW
Sarasota Bradenton Intl
Wed 12/9
12:45 pm-2:45 pm
Nonstop3h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
SarasotaChicago
SRQ Sarasota Bradenton Intl - MDW Chicago Midway
SRQMDW
Sarasota Bradenton Intl
Tue 11/10
6:10 am-12:05 pm
1 stop6h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$169
SarasotaChicago
SRQ Sarasota Bradenton Intl - MDW Chicago Midway
SRQMDW
Sarasota Bradenton Intl
Fri 12/4
6:24 pm-10:54 pm
1 stop5h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$170
SarasotaChicago
SRQ Sarasota Bradenton Intl - MDW Chicago Midway
SRQMDW
Sarasota Bradenton Intl
Tue 1/5
4:55 pm-10:10 pm
1 stop6h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$170
SarasotaChicago
SRQ Sarasota Bradenton Intl - MDW Chicago Midway
SRQMDW
Sarasota Bradenton Intl
Sat 11/7
7:05 am-11:30 am
1 stop5h 25m
Chicago Midway
Tue 11/10
3:00 pm-9:55 pm
1 stop5h 55m
$265
Showing 1-10 of 20 resultsSorted by cheapest first
Compare providers for flights from Sarasota to Midway
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 Sarasota to Midway in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Sarasota-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Sarasota-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Sarasota-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Sarasota-Chicago Midway 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 Sarasota-Chicago Midway 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 Sarasota to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Sarasota with our price prediction graph.
SRQ-MDW
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 Sarasota to Chicago Midway Airport
What is the cheapest time of day to fly from SRQ to MDW?
Find hourly flight availability from Sarasota to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 10, 2026.
When flying from Sarasota to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 15% versus a flight at noon.
How much does it cost to fly round-trip from Sarasota to Chicago Midway Airport?
Airfare is below average for this route at the moment.
Sarasota to Chicago Midway Airport flights typically cost between $309 and $419 in November.The cheapest round-trip price found within the last 5 days was $245 on Southwest (Nov 4-Nov 7).
The best insider tips for Sarasota to Chicago Midway Airport flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Sarasota to Chicago Midway Airport trip
Our travel experts
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated October 10, 2026.
Get a feel of what it's like to fly with Southwest from Sarasota to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.9
Entertainment
7.4
Crew
8.6
Comfort
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Entertainment
7.4
Crew
8.6
Comfort
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Sarasota to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 10, 2026.
Sarasota and Midway flights
Browse other Sarasota and Midway flight options. Last updated on October 10, 2026.
Other flights from Sarasota
Browse through other flights departing from Sarasota. Flights are based on user searches made on Cheapflights and were last updated on October 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Sarasota to Midway
Discover the top airline that operate flights from Sarasota to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$292 | Average$413 | FlexibilityNo cancel fee | On-time63% |