4* The Robey

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 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.

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.

Hampton Inn Chicago North-Loyola sits well north of Downtown in Rogers Park, giving you a more neighbourhood-based stay than most of GayMapper’s Chicago choices. It’s particularly useful if you want to explore the northern side of the city rather than spend the whole trip around the Loop. Rooms are modern and straightforward, breakfast is included, and there’s a rooftop terrace with views towards Lake Michigan. Loyola CTA station is just a short walk away, with Red Line trains running south through the city. This isn’t a nightlife-first choice — Northalsted and Andersonville both require a journey — but rates can be attractive compared with more central hotels. GayMapper tip: worth considering for value and transport links rather than proximity to the gay bars.

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.