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 Sarasota/Bradenton to Chicago (Midway) now!
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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 Sarasota/Bradenton to Chicago (Midway) now!
Sarasota/Bradenton, FL to Chicago (Midway), IL
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 38 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!
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 $135 (departing on 5/24)* |
|---|---|
| Departing from | Sarasota-Bradenton International Airport (SRQ) |
| Arriving at | Chicago Midway International Airport (MDW) |
| Average flight time | 2 hours 47 minutes |
| Distance | 1035 miles |
| 140† | Weekly flights |
|---|---|
| 1‡ | Nonstop flight per day Monday through Friday |
| 2 ‡ | Nonstop flights on Saturday |
| 2 ‡ | Nonstop flights on Sunday |
Other popular flights from Sarasota/Bradenton:
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 5/1/2025 and 5/31/2025. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 5/1/2025 and 5/31/2025.
A city of neighborhoods offers a nearly endless number of opportunities to get lost in new cultures, cuisines, and curiosities. The Loop, the central downtown area of the city, is a great place to start if you’re a first-time visitor. If the weather is agreeable, one of the best ways to enjoy the ...Loop is to take an architectural tour along the Chicago River. Experts on the stunning and iconic buildings will bring you up to speed quickly on the most important landmarks along the riverfront. If you visit during a colder part of the year, the downtown and River North neighborhoods are easily accessible by public transit. The Chicago ‘L’ train offers some stunning views as you cruise around above street level.
If you’d prefer to travel by land, start your adventure on the Chicago Museum Campus, home to the Field Museum, Adler Planetarium, and more. You’ll easily find the Chicago Lakefront Trail while you’re there. Rent a bike and follow it south to scenic Promontory Point or the Museum of Science and Industry. You can even stroll the main fairgrounds of the 1893 World’s Fair at the lakefront Jackson Park. Traveling north will give you easy access to a number of beaches and popular neighborhoods like Lincoln Park, Lakeview, and Edgewater. There’s no telling where your day might go when you start to explore the vibrant sights, sounds, and delicious smells of these historic neighborhoods.
If you’re an art lover, there’s no place better to be than Chicago. The local theater and music scenes have a national reputation to be reckoned with, and there is no shortage of venues―from world-class mixed-performance spaces to storefront arthouses―to keep you busy. If nature’s more your speed, it’s easy to get lost in the lush surroundings of the Lincoln Park Conservatory or the Chicago Botanic Garden. Plus, there are plenty of amazing dining experiences to be had. Get an authentic gyro in Greektown, haute cuisine in the West Loop, or tavern-cut pizza pretty much anywhere you go. No matter your taste, there’s somewhere to satisfy it in Chicago.
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.
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.