Escape the brutal Chicago winters and head south toward sunshine. Whether you follow the Mississippi down to New Orleans or cruise straight to the Gulf Coast beaches, these warm-weather road trips from Chicago offer the perfect antidote to lake-effect snow.
Chicago → St. Louis → Memphis → Natchez → New Orleans
Follow the Mississippi River south on one of America’s most iconic drives. Stop for BBQ in Memphis, explore antebellum Natchez, and arrive in the Big Easy for world-class food, jazz, and year-round warmth.
Chicago → Nashville → Birmingham → Pensacola → Destin
Drive through the heart of the South to reach the sugar-white sand beaches of the Florida Panhandle. Nashville makes an ideal overnight stop, and you’ll be on the beach in under two days.
Chicago → Springfield → Little Rock → Dallas → San Antonio → South Padre Island
Head deep into the heart of Texas for warm Gulf breezes on South Padre Island. Enjoy live music and Tex-Mex in San Antonio’s River Walk district before reaching this tropical barrier island.
Chicago → Louisville → Knoxville → Charleston → Savannah
Trade the Midwest cold for the mild charm of the Lowcountry. Explore Charleston’s historic cobblestone streets, then continue to Savannah’s Spanish-moss-draped squares and coastal island beaches.
Chicago → Indianapolis → Atlanta → Orlando → Tampa → Clearwater Beach
Hit the interstate south for theme parks, sunshine, and some of the best beach towns on the Gulf side of Florida. Clearwater Beach consistently ranks among the country’s best for white sand and warm water.