Chicago
The easiest big city to do alone
A solo day of the Art Institute, a lakefront walk and a food-hall dinner, all reachable on one transit pass with no car.
Solo travelers who want a walkable, transit-rich city where museums, the lakefront and food halls all work fine alone, with a safe, navigable downtown.
You only travel in winter; Chicago drops to 20ยฐF and the wind off the lake makes solo wandering miserable from December to March.
- Budget:
- $900-1,300 for 3 nights solo (incl. flights, central hotel, meals)
- Flights:
- From $110 round-trip from ATL or LAX (nonstop on United or American)