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 Savannah/Hilton Head 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 Savannah/Hilton Head to Chicago (Midway) now!
Savannah/Hilton Head, GA to Chicago (Midway), IL
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 21 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 $144 (departing on 4/23)* |
|---|---|
| Departing from | Savannah/Hilton Head International Airport (SAV) |
| Arriving at | Chicago Midway International Airport (MDW) |
| Average flight time | 2 hours 17 minutes |
| Distance | 758 miles |
| 106† | Weekly flights |
|---|---|
| 1‡ | Nonstop flight per day Monday through Friday |
| 2 ‡ | Nonstop flights on Saturday |
| 2 ‡ | Nonstop flights on Sunday |
Other popular flights from Savannah/Hilton Head:
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 4/1/2025 and 4/30/2025. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 4/1/2025 and 4/30/2025.
Known as the City of the Big Shoulders, Chicago has a variety of recreational activities for you to experience. From museums and famous landmarks to outdoor activities and lively nightlife, there’s plenty to discover on, in, and around Lake Michigan.
Outdoor enthusiasts may be surprised by all ...Chicago has to offer beyond just wandering the city and enjoying the architecture and parks. A great way to sightsee while getting some exercise in is kayaking the Chicago River. As you wind your way down the river, right beneath the Chicago skyline, you’ll get a unique perspective of buildings designed by Frank Lloyd Wright, Ludwig Mies van der Rohe, and other renowned architects. If you prefer pedaling to paddling, rent a bike and explore Chicago’s famed Magnificent Mile. By bike, you can also easily get to some of Chicago’s other legendary attractions such as Millennium Park and Buckingham Fountain, but be sure to stop for a visit to the city’s sprawling Museum Campus, which features the Adler Planetarium, Field Museum, and Shedd Aquarium.
History buffs and landmark fans can cross a lot of pivotal spots off their list during a trip to the Windy City. The Pullman National Monument, located on the city’s South Side, commemorates the first planned industrial community in the United States. Rising above all of Chicago is the Western hemisphere’s third-tallest building—the Willis Tower. Gather your courage and look straight down through a plexiglass floor of the observation deck to the ground 1,353 feet below. Elsewhere, guests can get a taste of the beauty of a bygone era of Chicago at Union Station. Featuring a breathtaking skylight and classical Corinthian columns, it’s no wonder that this stunning train station has been used as a backdrop in many movie productions over the years.
Foodies can also satisfy any and all of their cravings while in town. Outside of its world-famous Restaurant Row, Chicago has virtually endless choices to explore in its different ethnic enclaves. If you’re looking for some Latin flare, the Pilsen neighborhood has numerous authentic options. Curry lovers should head to West Ridge, the heart of Chicago’s Indian and Pakistani communities. Head to Greektown to sample the traditional spices that can be found in Mediterranean classics. And if you still have a hankering for other cuisines, such as Italian or Polish, you’re sure to find what you’re looking for elsewhere, in vibrant neighborhoods like the Heart of Italy and Old Polonia.
With so much to see and do all in one of America’s great cities, Chicago is just awaiting your arrival. So pack your sense of adventure and book your flight today.
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.