The Best Hotels in Illinois

An effortlessly cool revamp of a turn-of-the-century publishing house, this sophisticated B&B delivers a generous serving of industrial chic. Polished concrete and exposed steel rub up against Ottoman rugs, old timber floors and buffed-up workshop chairs. Provocative artworks share wall space with steer skulls and antique glass mirrors. Then there’s the Fulton Market location, which puts you just across the North Shore Channel from the Loop, with skyscraper views.

Is this a hotel, or a club for gents in top hats, teleported from the 1890s? The Chicago Athletic Association reclines lavishly behind a gothic facade facing Millennium Park, just yards from the Art Institute and pretty much everything else downtown. Inside, it’s all marble stairways, time-worn bookshelves, leather armchairs and sporting trophies. Rooms with vintage-inspired furniture make playful nods to the sporting past of the building – pommel horse for your clothes, anyone? What’s more, there are seven – yes, seven – places to eat and drink here.

You’ll know there’s something bohemian about the Freehand as soon as you see the frontage, with its hand-scrawled nameplate and vintage theater vibes. The bar and restaurant are crammed with old-fashioned wallpaper and tiki bar ornaments, and rooms and suites are full of mismatched details – coat-of-arms fireplaces, textured throw cushions, geometric rugs, mid-century sideboards – that somehow work seamlessly together as a whole. It’s irreverent, atmospheric and a whole lot of fun.

With a lavish lobby full of two-tone brickwork, convex mirrors and sultry lighting, the Thompson Chicago is the downtown dream, and the Near North Side location puts you within strolling distance of good eating and drinking and the sands of Oak Street Beach, just a block from the soaring steelwork of the John Hancock Center. It’s all about the views in the creatively themed rooms, with line-drawn artworks and huge windows framing sections of the Chicago skyline, lake shore and city lights.

Firstly, consider the location of Staypineapple, circled by the Loop. It’s two blocks to City Hall in one direction, and two blocks to Millennium Park in the other. Go two blocks north and you hit the Chicago Theatre; go two blocks southeast and you’ll reach the official start of Route 66. Floor space comes at a premium this close to the action, but rooms at Staypineapple are comfy and calm, with Keurig coffee-makers and views over a swathe of glass towers.

If you absolutely must be downtown, the Naperville setting might push the Hotel Arista off your shortlist, but there are perks to the Illinois tech corridor location. This sleek modern block rises above the CityGate campus, putting eating, drinking and live music within easy reach, and nearby, the I-88 running west to Iowa meets the I-55 running south to St Louis. It’s an inviting stop, with a full-service spa and big rooms with large windows to let in the light.

Everyone clamors for the center, but there’s life south of the Loop, with plenty going on around the University of Chicago campus and Jackson and Washington parks. Stay at the Sophy Hyde Park and you’ll detect a tangible student buzz, with the lake shore right on the doorstep. Artsy murals and framed artworks splash color around the rooms – even in the bathrooms – and Metra trains zip north to the Loop and south to the Museum of Science and Industry.

Edging into the Loop just below the Chicago River, this downtown hotel is walking distance from pretty much everything, from the Chicago Theatre to Millennium Park and the Art Institute – in other words, you’ll have culture on tap here. Sure, the hotel isn’t shy about putting Virgin branding on display, but the chambers – rooms, to you and me – have a calm maturity, with vaguely Nordic lines, downtown views and Tube logo rugs hinting at the brand’s British roots.

The crisp, traditionally styled rooms here will delight both business travelers and the more romantically inclined. Plump for the executive suite to get acres of space and a jetted tub, tough leather upholstery and views over the Illinois River. The softly lit Two25 restaurant serves up the usual suspects – steaks, burgers and breakfast omelets – with panache. Grab the breakfast-to-go option and walk the short distance to Peoria Riverfront Park.