Are you planning a trip to Chicago with your loved one? You can pack so much fun into your schedule. The city is home to numerous neighbourhoods, each offering something unique. Northalsted, also known as Boystown, is filled with welcoming people, great shops and restaurants. You can even follow The Legacy Walk to know more about the contributions of the LGBTQ+ community. Round up your day with a Blue Man Group performance at Briar Street Theatre or with a fun meal at Kit Kat Lounge & Supper Club. If dancing is on the cards, you can make your way to Roscoe’s Tavern or Sidetrack. You even have a wide variety when it comes to accommodations in Chicago. For options, take a look at this list of the best gay-friendly hotels in Chicago, Illinois.
We handpicked these listings carefully, considering (wherever possible) recent guest reviews, location, accommodation type, prices, availability of dates, decor, and the property's inclusivity for guests from all walks of life. The image galleries get refreshed with the latest updates regularly. They were last updated on April 24, 2025.
1. Four Seasons Hotel Chicago (from USD 493)
For a luxurious stay in Chicago, you can consider the 5-star Four Seasons Hotel Chicago. The property offers a range of rooms, from 376-sq.-ft. (34.93-sq-m) rooms to suites measuring more than 2700 sq. ft. (250.84 sq m) to accommodate your group. The rooms offer gorgeous views of the lake or the city’s skyline, so you can savour them from your private space.
The hotel is located on the Magnificent Mile and offers you easy access to shopping spots, eateries and more. To pamper yourself on your vacation, you can choose to indulge in a relaxing treatment at the on-site spa.
Four Seasons Chicago
197 meters (0.2 ft) from 875 North Michigan Avenue
2. The Peninsula Chicago (from USD 557)
The 5-star The Peninsula Chicago hotel boasts 339 rooms fitted with all luxuries to make your trip memorable. You will find hypo-allergenic linens, pillowtop mattresses, wardrobes and bathrooms with deluxe toiletries in your room. You can go around town in style using the hotel’s limousine service. When you are back, you can relax by swimming in the pool or just lounging by it.
The on-site spa boasts Ayurvedic treatments. You can savour delicious meals in the on-site restaurant Shanghai Terrace, where you can enjoy al fresco dining too.
The Peninsula Chicago
357 meters (0.3 ft) from 875 North Michigan Avenue
3. The Ritz-Carlton, Chicago (from USD 511)
The Ritz-Carlton, Chicago is located near Grant Park on Chicago’s Magnificent Mile. It is a 5-star property offering luxurious experiences to make your trip special.
Foodies will love the selection here. All three meals are available at Torali Italian Steak where the signature dishes include pasta, a variety of meats and seafood. If you are looking for a place to unwind and chill with your friends, you can choose Torali Bar or the Rooftop At Torali and sip on delicious cocktails. For a fresh cup of coffee to perk you up during the day, you can head to The Café.
The Ritz-Carlton, Chicago
119 meters (390.9 ft) from 875 North Michigan Avenue
4. The Langham, Chicago (from USD 616)
What do you look for in a hotel when you are planning a special trip? A pool and hot tub surely, and perhaps a spa for relaxation, a fitness centre so you can work out, and, when you want to head out, the comfort of a limousine service? All this and more are available to you when you stay at the 5-star The Langham, Chicago.
Choose from 316 air-conditioned rooms furnished with great care. You can relax in comfort here and order room service all through the day. No matter how busy your day is, you will feel refreshed after bathing in the tub or rainfall shower.
The Langham, Chicago
1.2 km (0.8 mi) from 875 North Michigan Avenue
5. Viceroy Chicago (from USD 305)
Viceroy Chicago is located in downtown Chicago and is close to the beach. You can visit popular attractions such as the Navy Pier, The Chicago Theatre and the Art Institute of Chicago from here. Getting around is easy as public transport access points are close by. The hotel is placed in a vintage building and some rooms offer beautiful views of Lake Michigan.
You will love the tastefully finished rooms decorated in a retro-chic style. Quality linens, Egyptian cotton sheets and down comforters make it a comfortable space as well. The property offers childcare services too, making it easy for parents to have some time on their own.
Viceroy Chicago
625 meters (0.4 ft) from 875 North Michigan Avenue
6. Waldorf Astoria Chicago (from USD 581)
Are you looking for luxury accommodation in Chicago that you can share, not only with your loved one but also with your pets? Choose Waldorf Astoria Chicago. This hotel is located on Chicago’s famous Magnificent Mile, making it easy for you to visit the city’s popular sights.
You will enjoy a unique dining experience here. The on-site lounge, Bernard’s, features a unique decoration style with Scottish influences. You can sip delicious drinks here while taking in the classic interiors. The on-site restaurant, The Brass Tack, offers sumptuous meals prepared from local ingredients.
Waldorf Astoria Chicago
413 meters (0.3 ft) from 875 North Michigan Avenue
7. Hotel Zachary Chicago, a Tribute Portfolio Hotel (from USD 319)
Design students will enjoy staying at the Hotel Zachary Chicago, a Tribute Portfolio Hotel. This hotel is named after the architect behind Wrigley Field, Zachary Taylor Davis, who was also a native of this city. You will love rooms with hardwood floors, luxurious oversized rainfall showers and designed toiletries. You can choose a suite which offers you great views of Wrigley Field as well.
If you love to begin your day keeping in touch with current events, you can use the free newspapers available here. Dry cleaning and laundry service are also offered, so you don’t have to worry about clean clothes.
Hotel Zachary Chicago, a Tribute Portfolio Hotel
6.17 km (3.9 mi) from 875 North Michigan Avenue
8. Thompson Chicago (from USD 191)
If you value a good night’s rest when travelling, you will enjoy staying at Thompson Chicago. All 247 rooms and suites are beautifully decorated with modern furnishings and beautiful art, allowing you to feel at home. Beds are fitted with premium linens so you can fall asleep peacefully. For a super luxurious stay, you can even pick a Penthouse Suite. Here, a private outdoor terrace and a billiards table are all yours, so you can party well into the night.
Feel refreshed in the mornings with the rainfall showers. You can have your meals at the on-site restaurant, or you can request room service.
Thompson Chicago, by Hyatt
479 meters (0.3 ft) from 875 North Michigan Avenue
9. Ivy Boutique Hotel (from USD 118)
If you have dreamed of sitting on a rooftop terrace, admiring gorgeous city views while sipping on a cold drink, this is your chance to make it a reality. Stay at Ivy Boutique Hotel and you can savour this experience at the hotel’s Sky Terrace rooftop lounge. Be it a hearty breakfast, snacks during the day or drinks in the evenings, you can find anything you need at the lobby restaurant Divine Lounge.
Those who wish to work will be able to do so in great comfort. All rooms are equipped with free Wi-Fi and a workspace. Your laptop will also be safe in the laptop safes in your room.
Ivy Boutique Hotel
613 meters (0.4 ft) from 875 North Michigan Avenue
10. Hotel Lincoln, part of JdV by Hyatt (from USD 156)
The first thing that catches your eye when you enter Hotel Lincoln, part of JdV by Hyatt is the front desk made from drawer fronts. Such eclectic design accents are found throughout this 4-star hotel, even in the 184 guest rooms. The restaurant boasts many on-site eateries, including a sushi restaurant and the popular J. Parker Rooftop Bar.
You can rent bicycles here and explore the neighbourhood. There is a gift shop on site, so you can easily pick up souvenirs for friends and family back home.
Hotel Lincoln
2.07 km (1.3 mi) from 875 North Michigan Avenue
Discover the magic of Chicago with your loved one
Don’t wait any longer to plan a trip to Chicago. Offering diverse activities, this city is a great place for a getaway with your significant other. If you are a member of the LGBTQ+ community, you can enjoy all that Chicago has to offer when you stay at one of the hotels listed above.
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