Jump to a day
Stops, in order
A city of barbecue, jazz, and fountains — legendary smoked meats, the birthplace of a jazz style, and two of the country's best museums.
Harry Truman's hometown and the jumping-off point for the great westward trails.
The live-entertainment capital of the Ozarks — dozens of theaters, an old-time theme park, and a lake in the hills.
Missouri's capital on a bluff above the Missouri River, with a statehouse full of Thomas Hart Benton's murals.
The Gateway to the West — the great silver Arch on the Mississippi, a free world's-fair park of museums, and one gloriously mad recycled-materials playground.
Mark Twain's boyhood town on the Mississippi — the whitewashed fence, the cave, and the river that shaped Tom Sawyer and Huck Finn.
Iowa's capital — a five-domed statehouse, a free downtown sculpture park, and the grounds of the country's most famous state fair.
Seven historic German communal villages, and the movie baseball diamond still cut into the Iowa corn.
The Twin Cities on the Mississippi — lakes and a milling history, a legendary music scene, world-class art, and the country's biggest mall. A full stay.
A rugged port city on Lake Superior and the wild, waterfall-laced shore that runs north from it.
A north-woods wilderness of interconnected lakes on the Canadian border — a national park you explore by boat, and the greatest canoe country in America.
The 'Cape Cod of the Midwest' — a peninsula of lighthouses, cherry orchards, harbor villages, and the traditional fish boil.
Titletown — home of the Packers and the hallowed Frozen Tundra of Lambeau Field.
The self-proclaimed 'Waterpark Capital of the World,' wrapped around the scenic sandstone gorges of the Wisconsin River.
One of the strangest attractions in America — a fever-dream house of endless bizarre collections — a few miles from Frank Lloyd Wright's Taliesin.
Wisconsin's capital and college town on an isthmus between two lakes — a grand statehouse, a lively student street, and a legendary farmers' market.
A hearty lakefront city of brewing and motorcycles, crowned by a museum with wings that open to the sky.
The city of big shoulders and bigger architecture — the Bean and the Art Institute, a river cruise past the skyline, world-class museums, blues, and deep-dish. A grand, full stay.
- 823Day 823 — The Bean & the Art InstituteFull day · 6h planned
- 824Day 824 — Architecture & the SkyFull day · 4h planned
- 825Day 825 — Museum CampusFull day · 6h planned
- 826Day 826 — The Mag Mile & the PierFull day · 4h planned
- 827Day 827 — Wrigley & the South SideFull day · 3h 30m planned
- 828Day 828 — Free DayFree day
- 829Day 829 — Free DayFree day
- 830Day 830 — Northwest to GalenaDrive day · 3h drive
A gorgeously preserved Victorian river town in Illinois's hilly northwest corner — and the home Ulysses S. Grant left to win the Civil War.
Illinois's capital and Abraham Lincoln's hometown — his home, his tomb, and a superb museum, all on Route 66.
The Racing Capital of the World — the hallowed Brickyard, a monument-ringed circle downtown, and the largest children's museum on earth.
Fifteen miles of Lake Michigan beach and towering dunes, with the Chicago skyline shimmering across the water.
'Beer City USA' on the Grand River — a world-class sculpture garden, a presidential museum, and a booming brewery scene.
Two old-country transplants — a Dutch town of tulips and windmills on the lake, and a 'Little Bavaria' with the world's biggest Christmas store.
A car-free Victorian island of fudge and horse-drawn carriages at the top of the mitt, and the cherry-and-wine country and giant dunes to the south.
Michigan's capital and, next door, the sprawling green campus of Michigan State.
The Motor City and the birthplace of Motown — a resurgent downtown, an incomparable history museum, and Diego Rivera's industrial masterpiece. A gateway to Canada, too.
The Rock Hall on Lake Erie, a superb free art museum, and a whole national park of waterfalls and a scenic railroad hiding between the city and Akron.
Ohio's capital and biggest city — a Greek-Revival statehouse, a hip arts district, and the brick streets of German Village.
The birthplace of aviation and home to the largest military aviation museum in the world.
A handsome river city of hills and a famous chili — with a suspension bridge that was a rehearsal for Brooklyn's. The last stop in the Midwest.