Stopping points from St Augustine to Chicago Midway International Airport:

• Start from St Augustine
• 2.5 hours to Valdosta, Georgia after driving about 160 miles / 250 km
• 3.5 hours to Atlanta, Georgia after driving about 230 miles / 370 km
• 4 hours to Nashville, Tennessee after driving about 250 miles / 400 km
• 2.5 hours to Louisville, Kentucky after driving about 180 miles / 280 km
• 2 hours to Indianapolis, Indiana after driving about 120 miles / 190 km
• 3 hours to Chicago Midway International Airport after driving about 190 miles / 300 km

Your total trip with all stops is around 1,110 miles / 1790 km, taking roughly 17 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 UST and MDW.

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Stopping points from UST to MDW

Start from St Augustine.

Valdosta, Georgia is stopping point #1 after driving about 160 miles (250 km) or 2.5 hours.

Atlanta, Georgia is stopping point #2 after driving about 230 miles (370 km) or 3.5 hours. Your total trip so far is about 380 miles or 620 km over roughly 5.5 hours of driving.

Nashville, Tennessee is stopping point #3 after driving about 250 miles (400 km) or 4 hours. Your total trip so far is about 630 miles or 1020 km over roughly 9.5 hours of driving.

Louisville, Kentucky is stopping point #4 after driving about 180 miles (280 km) or 2.5 hours. Your total trip so far is about 810 miles or 1300 km over roughly 12 hours of driving.

Indianapolis, Indiana is stopping point #5 after driving about 120 miles (190 km) or 2 hours. Your total trip so far is about 930 miles or 1490 km over roughly 14 hours of driving.

Finally, Chicago Midway International Airport is your destination after driving about 190 miles (300 km) or 3 hours. Your total trip with all stops is around 1,110 miles or 1790 km, taking roughly 17 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.