1 / 5
Midwest Loop
A 7-day driving-only loop through classic American Midwest cities, lakefronts, dunes, river towns, and one very big arch.
7days
22stops
DAY01
Depart → Lincoln Park Conservatory
Overnight in Lincoln Park Conservatory
- 09:00Depart· start
- 10:00⭐ Millennium Park
- 13:30Navy Pier
- 16:30Lincoln Park Conservatory· overnight
Accommodation
River North or Lincoln Park
DAY02
Depart → Detroit
Overnight in Detroit Riverfront
- 08:30Depart· start
- 10:15⭐ Indiana Dunes National Park
- 14:00The Henry Ford Museum of American Innovation
- 17:30Detroit Riverfront· overnight
Accommodation
Downtown Detroit or Corktown
DAY03
Depart → Cuyahoga Valley National Park
Overnight in Cuyahoga Valley National Park
- 09:00Depart· start
- 10:00⭐ Detroit Institute of Arts
- 13:30West Side Market
- 16:00Cuyahoga Valley National Park· overnight
Accommodation
Independence or Brecksville area
DAY04
Depart → Indianapolis
Overnight in Indianapolis Canal Walk
- 08:00Depart· start
- 10:45⭐ Hocking Hills
- 14:30German Village
- 17:30Indianapolis Canal Walk· overnight
Accommodation
Downtown Indianapolis
DAY05
Depart → Gateway Arch National Park
Overnight in Gateway Arch National Park
- 09:00Depart· start
- 09:30⭐ Indianapolis Motor Speedway Museum
- 13:30Cahokia Mounds State Historic Site
- 16:30Gateway Arch National Park· overnight
Accommodation
Downtown St. Louis or Central West End
DAY06
Depart → Wisconsin State Capitol
Overnight in Wisconsin State Capitol
- 08:00Depart· start
- 09:00⭐ St. Louis Cathedral Basilica
- 13:30Galena Historic District
- 17:30Wisconsin State Capitol· overnight
Accommodation
Downtown Madison near Capitol Square
DAY07
Olbrich Botanical Gardens → Chicago
- 09:15⭐ Olbrich Botanical Gardens· start
- 12:30Milwaukee Lakefront
- 16:30Chicago Riverwalk
Heads Up
- Day 4: 6h 42m driving — plan rest stops
- Day 6: 7h 18m driving — plan rest stops
- National park entry or passes can help if you’re adding extra federal sites
- check market/museum opening days before locking meals around them
- keep toll money or an electronic toll option ready around Chicago and northern Indiana