In Chicago’s former meatpacking district, The Hoxton sits among
some of the city’s best galleries, boutiques and eateries. After a
day exploring the neighbourhood, return to kick back by the rooftop
pool and dine in the Peruvian-inspired cevicheria on the terrace.
Need to catch up on emails? Plug in in the lobby’s co-working space
before delving into the hotel’s depths for a nightcap in the
basement bar.

Naturally slotting into artsy West Loop, Ace Hotel’s interiors
are draped with locally sourced artwork and furnishings while rooms
are designed with a minimalist, monochromed aesthetic, plus there’s
a rooftop area overlooks the city skyline. Hop between the
neighbourhood’s bars and restaurants (the area is quickly becoming
Chicago’s newest food scene) and round the day off with nibbles and
cocktails at Ace’s bar, City Mouse.

Book lovers, this is the place for you. Rooms are dedicated to
Chicago’s literary figures such as Stuart Dybek and Audrey
Niffenegger, while the mid-century armchair by the double-sided
concrete fireplace is a covetable spot for snuggling up. If you get
peckish, pop into the butler’s pantry where homemade cookies and a
cuppa make the perfect companions for your favourite book.

Perfectly placed for exploring the city beyond tourist traps,
this art-deco hotel is located between the creative neighbourhoods
of Wicker Park and Bucktown. Book into the Annex Loft where urban
warehouse spaces have been converted into roomy bedrooms, and spend
days lazing by the rooftop pool, feasting on comfort food in Café
Robey and sipping on cocktails in front of the floor-to-ceiling
windows.

Proving that hotels can be more fun than fancy, this whimsical
bolthole is filled with science-themed quirks and trinkets.
Magnifying glasses, copper-tubing, towering bookshelves and
portraits of great minds past adorn walls, while the restaurant and
bar serves innovative dishes and drinks with thematic twists. If it
all gets a bit much, head to Lake Michigan for a dose of the great
outdoors – it’s just a 10-minute walk from the hotel.

Kimpton Gray Hotel is a go-to for those in need of a little TLC.
Book into a Spa Room, where the bathrooms are decorated with
abstract-tiled walls, a walk-in shower and a freestanding tub. Drag
yourself away from your room for a tipple at either Vol. 39, the
lobby wine bar, or Boleo, the rooftop bar, or dine on new American
cuisine at Steadfast restaurant. Return to your room suitably
satiated to collapse in king-size beds.

This retro-themed hotel is filled with sports paraphernalia and
boutique touches. Enter the lobby to check in beneath an
installation of wooden tennis rackets, trophy racks and
wall-mounted dartboards. Head straight to the speakeasy Janitor’s
Closet for innovative cocktails before testing your skill on the
hotel’s own vintage-style slot car racing racks.

This boutique hotel is the ideal spot for hunkering down in the
Windy City. Nestled among the skyscrapers of downtown Chicago,
Freehand’s art-deco design and trendy interiors draw visitors to
it’s fireside chairs on chilly evenings. Sip on herbal infusions
and innovative drinks at the Broken Shaker bar – between Thursday
and Saturday it also hosts Tacoteqa, when it serves lip-smacking
tacos, quesadillas and margaritas.

Right next to Wrigley Field in bustling Wrigleyville, The
Wheelhouse is a starting-point for a culture-filled trip to
Chicago. Map out your day from the hotel’s rooftop before exploring
the neighbourhood. Return to taste-test your way through the
cocktail menu at the hotel’s speakeasy Tinker to Evers, and stock
up on sweet treats from Bodega to take to your room.