3* Versey Days Inn

The Peninsula is one of Chicago’s standout luxury hotels, just off Michigan Avenue in the heart of the Magnificent Mile. Rooms are spacious and polished, while the hotel has the kind of facilities you’d expect at this level, including an excellent spa, indoor swimming pool, restaurants and its well-known afternoon tea. The location is extremely convenient for shopping and many of Chicago’s central attractions, with the lakefront and Museum of Contemporary Art also nearby. Northalsted and Andersonville are several miles north, so this isn’t the place to stay specifically for gay nightlife. GayMapper tip: if you want full five-star luxury and sightseeing convenience, rather than gay bars outside the door, The Peninsula is hard to fault.

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.

The Willows sits on a residential street in Lakeview, offering a quieter and more traditional base within reach of both Lincoln Park and Chicago’s Northalsted gay scene. It’s a smaller hotel with a cosy feel rather than a long list of facilities, and rooms have a classic style. Lake Michigan and Lincoln Park are nearby, while the bars around Northalsted can be reached on foot, although they’re not immediately outside the hotel. Downtown requires a short journey, but public transport links from Lakeview are good. GayMapper tip: a comfortable middle ground if you want to stay near the gay neighbourhood without being right in the thick of the nightlife.

Viceroy Chicago combines five-star style with a Gold Coast location that feels a little more residential than the busiest parts of the Magnificent Mile. Rooms have a smart contemporary design, while the rooftop pool and bar are standout features during warmer months. Oak Street Beach, Michigan Avenue and some of Chicago’s best-known shopping and restaurants are all close by. As with the other Gold Coast hotels, the trade-off is distance from Northalsted and Andersonville, so you’ll need transport for the main gay nightlife. GayMapper tip: particularly appealing if you want modern luxury and a stylish rooftop scene while keeping Downtown Chicago firmly at the centre of the trip.

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.

Best Western Plus Hawthorne Terrace is particularly well placed if Chicago’s gay nightlife is high on your agenda. It sits in Lakeview, within walking distance of the bars and clubs around Northalsted, while Wrigley Field is also close by. Rooms are comfortable rather than flashy, with useful extras such as refrigerators, microwaves and coffee makers. There’s also a small fitness room, sauna and outdoor courtyard, and breakfast is included. The nearby Belmont and Addison CTA stations make getting Downtown straightforward, so you don’t have to choose completely between nightlife and sightseeing. GayMapper tip: a practical, good-value choice for staying close to the main gay scene without paying boutique-hotel prices.