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4* The Robey
The Robey, West North Avenue, Chicago, IL, USA
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.
Hotels you might like in Chicago
5* The Peninsula Chicago
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.
3* The Willows Hotel
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.
4* Hotel Zachary
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.
5* Viceroy Chicago
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.
4* Thompson Chicago
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.
3* Majestic Hotel
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.
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