5* The Peninsula Chicago

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.

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.

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.

The Hotel at Midtown is a little different from Chicago’s typical city hotels. It forms part of the huge Midtown Athletic Club complex, making the sports, fitness and wellness facilities a major part of the experience. Rooms are modern and stylish, while guests have access to extensive facilities including fitness areas, swimming pools, tennis and spa services. The location between Bucktown and Lincoln Park is less convenient for conventional sightseeing than Downtown, and the main Northalsted gay scene isn’t on the doorstep either. It works particularly well if you like the idea of combining a Chicago city break with serious gym and leisure facilities. GayMapper tip: one to choose for the facilities rather than the location — especially if a good hotel gym means rather more to you than a treadmill in a basement.

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.