Freehand Chicago

Character and identity

Set in a vintage building just off the Magnificent Mile in River North, the Freehand is a hostel-hotel hybrid that takes design seriously without taking itself too seriously. Bunk-style shared rooms sit alongside private rooms kitted out with colourful throw rugs, textile wall hangings, wooden credenzas doubling as desks, and outsized TVs. The lobby hums with laptop workers by day. Broken Shaker, the rooftop-tropical cocktail bar, pulls a strong local crowd, while Café Integral handles breakfast, lunch and serious coffee. The register throughout is bohemian, sociable, and unfussy.

Who's it for

Bottom line

The pitch here is design-forward fun at hostel-adjacent rates in a neighbourhood that normally commands a steep premium, and that value equation is the whole reason to book. Spend the money on a private room rather than a bunk if you want a proper night's sleep, and plan to hit Broken Shaker on a weeknight to avoid the queue.