4* Hotel Zachary

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.

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.

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.

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.

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.

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.