The Guesthouse Hotel ★★★★

A Failed Condo Building Turned All-Suite Hotel

The Guesthouse Hotel began as a luxury condo development in 2008, on North Clark Street in Chicago's Andersonville neighborhood, and the recession that followed left developer Dave Krug with finished units and no buyers. He and his wife Simona turned the building into short-term rentals, then into a full all-suite hotel, built around a single motto: live like a local. That origin still shapes the place. Suites carry hardwood floors, granite kitchens, fireplaces, and spa-quality steam showers rather than the compact rooms a conventional hotel would have built on the same footprint, and the clubroom and rooftop gardens read like amenities designed for residents, not just guests passing through.

Why It Works

We chose The Guesthouse Hotel because its all-suite format and residential detailing give it a genuine point of difference from the downtown towers most visitors default to. Twenty-five suites, each with a full kitchen, a private balcony with a gas grill, and in many cases a washer and dryer, make a multi-night stay feel closer to borrowing an apartment than booking a room, and the penthouse units with private rooftop gardens push that further still. Frommer's named it one of Chicago's best hotels off the beaten path, and the independent ownership shows in details a chain would standardize away.

Why This Location

Andersonville, bordering Ravenswood and Uptown, trades the Loop's density for a strip of independent restaurants, bookstores, and boutique shops along North Clark Street, with the Lake Michigan lakefront and Wrigley Field both a short ride away. The Red Line connects to downtown in about fifteen minutes on foot to the nearest stop, close enough for a day in the Loop without staying in the middle of it. It is a neighborhood built for walking rather than sightseeing, historically Swedish and now one of the city's most mixed and independent-minded commercial strips, and the hotel's address puts guests inside that character rather than at its edge.

Fast Facts

• Price: €€ (upscale, suite format)

• Vibe: residential, independent, neighborhood-first

• Rooms: 25 all-suite, one- to three-bedroom configurations

• Best For: extended stays, families, travelers wanting a neighborhood base

• Our Favorite Thing About the Hotel: the penthouse suites' private rooftop gardens

• Dining: in-suite gourmet kitchens, room service from a local kitchen partner

• Amenities: clubroom and library, fitness center, gas-grill balconies, pet-friendly

• Attractions: Andersonville's restaurant row, Lake Michigan lakefront, Wrigley Field

Suites Built Like Apartments, Not Hotel Rooms

Every suite at The Guesthouse Hotel is built around a full kitchen and a living area rather than a bed and a desk, and the configurations run from one bedroom up to three, making the property as workable for a family or small group as for a solo business traveler staying a week. Hardwood floors, granite counters, and fireplaces in the deluxe units carry the residential logic through to the finishes, and most suites include a washer and dryer, a detail aimed squarely at guests staying long enough to need one. It is a hotel designed around the assumption that a stay might run past a weekend.

Penthouses With Private Rooftop Gardens

The 2014 expansion added penthouse suites with their own private rooftop gardens, the property's clearest expression of its apartment-building origins. Paired with the ground-floor clubroom and library, the rooftop spaces give longer-staying guests somewhere to spend an evening without leaving the building, a rarity among boutique properties this size. The steam showers and gas fireplaces in select units push the suites toward a genuinely upscale register, closer to a well-appointed rental than a hotel room dressed up for photographs.

Before You Book

The Guesthouse Hotel suits travelers who want space, a kitchen, and a real neighborhood rather than a view of the Loop skyline, families and extended-stay guests especially. Anyone set on walking to Michigan Avenue or the Magnificent Mile should look downtown instead, Andersonville is a Red Line ride from that kind of itinerary, not a walk. For a Chicago stay built around living somewhere rather than passing through, this address and its apartment-style suites are a well-judged, independently run choice.