Whether you're traveling for business or pleasure, solo, or with the whole family, you'll enjoy the flexibility of flying Southwest®.
Find your next flight from Chicago (Midway) to Sarasota/Bradenton now!
Whether you're traveling for business or pleasure, solo, or with the whole family, you'll enjoy the flexibility of flying Southwest®.
Find your next flight from Chicago (Midway) to Sarasota/Bradenton now!
Chicago (Midway), IL to Sarasota/Bradenton, FL
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 17 travel days available. Fares are updated hourly. Fares displayed on external channels may no longer be available at time of booking. To find the most updated fare, please visit Southwest.com.
Southwest seats are first come, first served based on check-in order. But there are ways to board the plane earlier!
We make bag-checking a breeze with our flexible baggage policy. Here’s how to make your journey even smoother:
Take advantage of inflight entertainment with free movies4, free live TV5, free texting6, and $8 inflight Internet7.
We also offer free sodas, coffee, and snacks8—learn more about the inflight food and beverage experience.
Have a change of travel plans? We offer free same-day standby for all fare types. This means that you can retain your current flight while listing for standby on an earlier flight. If a seat becomes available, it’s yours at no charge!
Rapid Rewards Members can redeem their points for flights, hotel stays, rental cars, gift cards, and more. And your points never expire!
| Fare | Fly one-way from $159 (departing on 3/25)* |
|---|---|
| Departing from | Chicago Midway International Airport (MDW) |
| Arriving at | Sarasota-Bradenton International Airport (SRQ) |
| Average flight time | 2 hours 38 minutes |
| Distance | 1035 miles |
| 99† | Weekly flights |
|---|---|
| 1‡ | Nonstop flight per day Monday through Friday |
| 1 ‡ | Nonstop flight on Saturday |
| 1 ‡ | Nonstop flight on Sunday |
Other popular flights from Chicago (Midway):
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 1/1/2025 and 1/31/2025. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 1/1/2025 and 1/31/2025.
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 17 travel days available. Fares are updated hourly. Fares displayed on external channels may no longer be available at time of booking. To find the most updated fare, please visit Southwest.com.
Sandy beaches? Check. World-class museums? Check. Fresh seafood and waterfront dining? You got it! Sarasota and nearby Bradenton are great destinations for every kind of traveler, whether you’re looking for a fast-paced cultural tour or a few peaceful moments laying out in the sun. Start your visit to Florida’s Gulf Coast at Siesta Key Beach, a picture-perfect family beach with some of the softest sand around. And that’s not an empty claim, either—Siesta Key Beach’s sand is mostly made up of quartz, in contrast to most other beaches that have sand derived from pulverized coral. Have fun in the sun and take advantage of the tennis courts and volleyball nets or lay out a towel and catch up on some reading.
When you’re ready for a break from the sun, head over to one of the many museums and cultural institutions that Sarasota and Bradenton have to offer. Learn something new about automotive history at the Sarasota Classic Car Museum full of nostalgic, famous rides. If you’re curious about Sarasota’s wildlife, make your way to the Mote Marine Laboratory & Aquarium. At this public aquarium that doubles as a research center, visitors can get up close to seahorses, sharks, colorful fish, stingrays, sea turtles, and more reef animals.
Getting out on a hike or taking a boat ride is another Sarasota/Bradenton experience that should not be missed. Grab your life vest and take a kayak through the mangrove tunnels, a type of tree that is native to Florida’s subtropical marshy wetlands. There will be plenty of birds to keep you company on your journey, including osprey, wood storks, pelicans, and—if you’re lucky—you might even spot a bald eagle. For a chance to encounter bigger animals, check out the Big Cat Habitat and Gulf Coast Sanctuary. Camels, bears, tigers, monkeys, and more rescued rare species are cared for and rehabilitated here in addition to domestic animals like goats and donkeys. Round out your flora-and-fauna immersion at Lake Manatee State Park, a 556-acre area that’s also open for swimming, boating, fishing, and camping.
1EarlyBird Check-In® pricing starts at $15 one-way, and is subject to availability. Pricing may vary based on the popularity and length of each (one-way) flight. Please see optional travel charges for more details.
2Upgraded boarding prices and benefits are per eligible segment. Flights must be within 24 hours of departure to be eligible for upgraded boarding.
3First and second checked bags. Weight and size limits apply.
4Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
5Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
6Texting only allows access to iMessage and WhatsApp (which must be downloaded and activated before connecting to SouthwestWiFi).
7Internet access for $8 per device from takeoff to landing. Price is subject to change. May not be available for the full duration of flight. In order to provide a top-notch Internet experience, we prohibit access to certain high-bandwidth applications and websites. We also prohibit access to certain obscene or offensive content.
8Flights traveling 175 miles or less will have only water available. Complimentary snacks are served on flights over 175 miles. If you’re flying between Hawaii and the continental U.S., you’ll have even more snacks to choose from.
9Free same-day standby: You can list for same-day standby for an earlier flight via a Southwest Customer Service Agent at the airport or the Southwest app or mobile web. You must request to be added to the same-day standby list at least 10 minutes prior to the scheduled departure of your original flight or the no-show policy will apply. If using the app or mobile web, you must list your name 30 minutes ahead of scheduled departure. You will receive a message based on the contact preference selected during booking if you are cleared on the flight. Group bookings and Unaccompanied Minors are not eligible for same-day standby. You will be required to pay any government taxes and fees associated with these itinerary changes but refunds will be provided. Your original boarding position is not guaranteed on your standby flight. Southwest Business Customers booked through travel agencies may need to see a Southwest agent at the airport for a standby listing. See Southwest.com/standby for more details.