3* Majestic Hotel

The Drake is one of Chicago’s classic grand hotels, occupying a prominent position at the northern end of the Magnificent Mile close to Oak Street Beach and the Gold Coast. Expect traditional rather than cutting-edge luxury, with an imposing historic building, elegant public spaces and a real sense of old-school Chicago. The location is excellent for shopping, restaurants and central sightseeing, with the lakefront just outside. You’ll be well away from the main gay nightlife around Northalsted and Andersonville, so evenings out will involve a taxi, rideshare or public transport. GayMapper tip: choose The Drake for history, atmosphere and a prime central location rather than proximity to Chicago’s 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.

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.

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.

City Suites has one of the handiest locations in Lakeview, just beside Belmont CTA station and within easy walking distance of the bars around Northalsted. That makes it a particularly convenient base if gay nightlife is going to be a big part of your Chicago trip. The hotel has an older, Art Deco-influenced feel, with comfortable rooms and a more intimate atmosphere than the big Downtown hotels. Wrigley Field is also within walking distance. With Red, Brown and Purple Line trains practically outside, Downtown Chicago is easy to reach when you want to switch from nightlife to sightseeing. GayMapper tip: location is the big selling point here — especially if you want the gay bars close by and excellent public transport.

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.