If you're looking for a meeting place or a good stop around ½ or halfway between Phenix City and Chicago, you can try Bowling Green, KY, which is almost 6 hours north of Phenix City, or about 6½ hours south of Chicago.
About ¼ or a fourth of the way, you can stop at Chattanooga, TN. This is about 3 hours north of Phenix City.
About ⅓ or a third of the way, you can stop at Murfreesboro, TN. This is about 4½ hours north of Phenix City.
About ⅔ or two thirds of the way, you can stop at Columbus, IN. This is about 8½ hours north of Phenix City, or almost 4 hours southeast of Chicago.
About ¾ or three fourths of the way, you can stop at Indianapolis, IN. This is about 9 hours north of Phenix City, or about 3 hours southeast of Chicago.
If you drive straight through without stopping at all, the total distance is 823 miles. The distances shown above don't include local roads to get into each town, so if you're planning a long road trip, make sure you factor in traffic and road conditions, rest stop breaks, and interesting detours along the way. If you're in a rush, you can do the trip with zero stops, and your total travel time would be around 12 hours, 15 minutes.