Stopping points from Chicago O'Hare International Airport to Southwest Florida International Airport:

• Start from Chicago O'Hare International Airport
• 3.5 hours to Indianapolis, Indiana after driving about 200 miles / 330 km
• 8.5 hours to Atlanta, Georgia after driving about 530 miles / 860 km
• 5.5 hours to Gainesville, Florida after driving about 340 miles / 540 km
• 4 hours to Southwest Florida International Airport after driving about 260 miles / 420 km

Your total trip with all stops is around 1,330 miles / 2150 km, taking roughly 21.5 hours for the whole trip. If you want to see every small town along the way, you can get a full list of cities between ORD and RSW.

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Stopping points from ORD to RSW

Start from Chicago O'Hare International Airport.

Indianapolis, Indiana is stopping point #1 after driving about 200 miles (330 km) or 3.5 hours.

Atlanta, Georgia is stopping point #2 after driving about 530 miles (860 km) or 8.5 hours. Your total trip so far is about 740 miles or 1190 km over roughly 12 hours of driving.

Gainesville, Florida is stopping point #3 after driving about 340 miles (540 km) or 5.5 hours. Your total trip so far is about 1,070 miles or 1730 km over roughly 17.5 hours of driving.

Finally, Southwest Florida International Airport is your destination after driving about 260 miles (420 km) or 4 hours. Your total trip with all stops is around 1,330 miles or 2150 km, taking roughly 21.5 hours for the whole trip.

Stopping point calculator

Travelmath helps you figure out where to stop when planning a long road trip from one location to another. The best stopping point for an overnight hotel stay or a break from driving often depends on how far or how long you want to drive before pausing to rest. You can find the closest city to your stopping point to look for hotels, or explore other cities and towns along the route. Use this as a road trip planner when you're driving cross-country or mapping a route with multiple stops.