5* The Peninsula Chicago

The Guesthouse Hotel is one of GayMapper’s favourite Chicago choices, particularly if you prefer the neighbourhood feel of Andersonville to staying Downtown. Accommodation is apartment-style, with spacious one-, two- and three-bedroom suites featuring full kitchens and living areas, making it especially useful for longer stays or trips with friends. The surrounding Andersonville neighbourhood has restaurants, independent shops and a strong LGBTQ+ presence, with several queer venues within easy reach. You’re well north of the major Downtown sights, but public transport makes them accessible and Northalsted is also straightforward to reach. GayMapper tip: an excellent option if you want space, a genuinely local neighbourhood and easy access to Chicago’s LGBTQ+ life.

Sitting directly opposite Wrigley Field, Hotel Zachary puts you in one of Chicago’s liveliest neighbourhoods and within easy reach of the Northalsted gay scene. The hotel has a smart contemporary style with plenty of local character, while the surrounding streets are packed with restaurants and bars. Rooms are polished and modern, with some overlooking the ballpark. Addison Red Line station is just a short walk away, making Downtown easy to reach and giving you a straightforward connection through Lakeview. GayMapper tip: a stylish choice if you want a proper neighbourhood atmosphere, easy access to gay nightlife and a more upscale feel than many of the nearby hotels.

Thompson Chicago brings a stylish boutique feel to the Gold Coast, one of the city’s smartest central neighbourhoods. Oak Street, Michigan Avenue and the lakefront are all close by, making this an excellent base for shopping, restaurants and sightseeing. Rooms have a contemporary, slightly residential look rather than generic business-hotel styling, and the overall atmosphere is polished without feeling overly formal. Chicago’s main gay nightlife is further north around Northalsted and Andersonville, so you’ll need transport for a night out there. GayMapper tip: a good fit if you want a fashionable central hotel and plan to divide your time between sightseeing, restaurants and nightlife rather than basing the whole trip around the gay scene.

The Robey occupies a landmark Art Deco building right at the heart of Wicker Park, giving you a very different Chicago experience from the big hotels around the Magnificent Mile. Rooms combine modern design with the character of the original building, while the rooftop spaces are a highlight, offering impressive views back towards the Downtown skyline. Wicker Park itself is packed with restaurants, bars, cafés and independent shops, making it a great area for evenings closer to home. The main gay nightlife in Northalsted and Andersonville isn’t within walking distance, although transport connections are good. GayMapper tip: a strong choice if neighbourhood character, design and rooftop drinks matter more to you than staying close to the traditional gay scene.

Hotel Versey gives the familiar Days Inn brand a rather more colourful personality, with design inspired by Chicago’s music, art and neighbourhood culture. Its Lincoln Park location puts you between Downtown and Northalsted, so it can work particularly well if you want reasonably easy access to both sightseeing and gay nightlife without paying central Chicago prices. The bars around Northalsted aren’t immediately outside, but they’re within easy reach. Rooms are contemporary and informal, and there are plenty of restaurants and shops in the surrounding area. GayMapper tip: a useful value option if location matters more than luxury and you want to split your time between central Chicago and the gay scene.

Majestic Hotel offers a quieter alternative in Lakeview while still keeping you within reasonable reach of Northalsted’s gay bars and clubs. It occupies a residential spot east of Wrigley Field, giving the hotel a more neighbourhood feel than the busier properties around Belmont. The historic building has a cosy, traditional style rather than a sleek contemporary look, and breakfast is included. Lake Michigan and the lakefront are also nearby. You’ll have a little further to walk for the main nightlife than from City Suites or Hawthorne Terrace, but it can be a pleasant compromise if you prefer somewhere calmer. GayMapper tip: best for travellers who want Lakeview convenience without staying right in the middle of the action.