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Gay Friendly Hotels
10 Best Gay-Friendly Hotels In Chicago, Illinois

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.
What To Buy
What To Buy In Chicago, Illinois

There are lots of reasons to visit Chicago, Illinois: the city is full of museums, sporting venues, iconic buildings, and delicious restaurants. It’s also a city with tons of shopping opportunities. The Magnificent Mile, the northern section of Michigan Avenue and Chicago’s commercial center, has over 460 retailers and three shopping centers. That doesn’t even include all of the shops to be found in Chicago’s other neighborhoods! If just the thought of wandering through all those stores makes you feel tired, here is a list of the top things to buy in Chicago to help you narrow down your shopping goals!
Things To Do
10 Things To Do To Enrich Your Bolingbrook, Illinois Experience

If Bolingbrook was a painting, then it would definitely be a colorful one because it is full of experiences you can venture on. In your kids' eyes, it is full of fun with waterparks, interesting golfing areas, farms and play lands. From your view, it will be an enjoyment and discovery journey with natural hidden gems and movie and shopping experiences. No matter what age you are, the Bolingbrook experience will not disappoint.
Airbnb
Top 11 Airbnb Vacation Rentals In Arlington Heights, Illinois

The village of Arlington Heights is a suburb of Chicago. It sits about 25 miles (40 km) northwest of the downtown area. The town is home to the Arlington Track, which has been called the "most beautiful track in America." They have been racing thoroughbred horses here since 1927. During the summer, the track is a popular place for locals and tourists alike to enjoy a day of racing and fun. Another option is to spend the day outdoors at Lake Arlington, which has bike and walking paths. During the summer, there are canoes for rent, and you can take sailing lessons too. For more ideas for activities, check out the best things to do in and around the area. If you're visiting soon, click here to find the top Airbnb vacation rentals in Arlington Heights, Illinois.
Airbnb
12 Handpicked Airbnb Vacation Rentals Near Edgewater, Chicago

Chicago provides one of the best apartments around where they are conveniently located near either the subways or the nearest transportation system. They have a range of apartments - from modern and chic to vintage looking - but one thing is for sure, is that they all are cosy and the hosts make sure the stay is a good and unforgettable one. It is also true that these Airbnbs are often strategically located near supermarkets which makes grocery runs a quick and fuss-free one. Airbnb vacation rentals in Andersonville see a lot of visitors, but the neighborhood next to it, Edgewater, also has some amazing places to stay. Find out where to head to for affordably priced accommodations when in Edgewater. Scroll below to check out the best Airbnb vacation rentals near Edgewater, Chicago.
Hotels With Airport Shuttle
Top 10 Hotels With Airport Shuttle In Schaumburg, Illinois

Boasting a convenient location close to O’Hare International Airport, Schaumburg is a thriving suburb and village in Illinois. Although it originated as a farming community, the destination is now home to numerous businesses and serves as one of the state's economic bases. Explore Schaumburg's diverse attractions during your stay here. You can visit The Sculpture Park to admire unique outdoor installations by American and international sculptors amidst lush greenery. Volkening Heritage Farm is an ideal spot to discover the history of the area in an open-air setting spread across 135 acres (55 hectares). If you're visiting with family, stop by Mastermind Escape Games Schaumburg for a fun-filled afternoon or The Water Works Indoor Water Park for a refreshing day out. Traveling to this charming suburb via a plane? Let your hotel worry about your airport transportation! Read on to find the top hotels with airport shuttle in Schaumburg, Illinois.
Things To Do
8 Best Things To Do In Plainfield, Illinois

In need of a nice place for a little vacation with your family or friends? Then check out the village of Plainfield, which is located in Chicago's suburbs. It's the perfect getaway from the fast pace of metropolitan life. There's plenty of interesting attractions in Plainfield to keep you busy, so check out our list of best things to do when you're there.
Things To Do
9 Best Things To Do In Hoffman Estates, Illinois

Hoffman Estates is a village in Illinois in Cook County and a suburb of Chicago. If you're planning a visit to the area in the future, you should check out that list of best things to do in Hoffman Estates, Illinois.
Things To Do
7 Best Things To Do In Lisle, Illinois

Lisle, Illinois is a village in the Chicago metropolitan area with a population of about 21,000 people. What Lisle may lack in population size, it makes up for in attractions. Lisle was permanently settled in 1832 at the end of the Black Hawk War. The tiny settlement grew and grew. Now major corporations, such as Millward Brown, have their headquarters there. Lisle is more than just a corporate center though. Lisle has fast sports teams, quiet walks in nature and everything in between. Its appeal attracts people from all across the world, learn more about the best things to do in the area!
Romantic Staycations
14 Handpicked Romantic Staycations In Chicago, Illinois

Chicago is one of the top destinations in North America when it comes to both business and pleasure. Couples looking for a romantic getaway will be happy to find an almost endless list of possibilities in the Windy City. You could wander around Lake Michigan’s shoreline, explore the many gourmet options and Viator tours, or check out the Magnificent Mile. If you’re looking to surprise your partner with a romantic gesture, you could try taking a carriage tour of Michigan Avenue, hop on the Navy Pier Ferris Wheel, or head over to 360 Chicago, for breathtaking city views. There are also countless restaurants with a view where you can treat your partner. If you want to take a break from all the outdoor activities, stay in your hotel room and relax with a spa massage, have a drink on the rooftop bar, or check out the pool, read on, as we’re about to show you the best romantic staycations in Chicago, Illinois.
Vrbo
10 Best Vrbo Vacation Rentals Near McCormick Place, Chicago, Illinois

Located 2 miles (3.22 kilometers) south of downtown Chicago, Illinois, McCormick Place is a convention center that stands near the shores of Lake Michigan. It holds the distinction of being the largest convention center in North America. Every year, the convention center attracts about 3 million visitors who come to attend trade shows and meetings. Some notable events held here include the Chicago Auto Show in February, The Inspired Home Show in March, and The National Restaurant Association Show in May. For a change, visitors in Chicago could also check out the nearby McCormick Place Bird Sanctuary, which is a sanctuary for nature lovers. If you're planning a trip to this captivating region and don't know where to stay, we've got you covered. Scroll down for the best Vrbo vacation rentals near McCormick Place, Chicago, Illinois.
Airbnb
Top 11 Airbnb Vacation Rentals In & Around Bolingbrook, Illinois - Updated 2026

Airbnbs vacation rentals in Bolingbook offer the perfect home-away-from-home for travelers who want to stay somewhere relatively quiet yet accessible to Chicago's urban conveniences. These properties are located near restaurants and stores, and are accessible via highways. Ranging from large houses perfect for families and smaller rooms for solo occupants, there's a property for every kind of traveler. If you're traveling with your family, some rentals also offer a children's playroom and spacious yards and patios. We've shortlisted Airbnbs for your vacation in Bolingbrook, Illinois. Discover these stays below:
Airbnb
Top 10 Airbnb Vacation Rentals In Wrigleyville, Chicago, IL

Home to the talented Chicago Cubs, one of the Chicago's two Major League Baseball (MLB) franchises, Wrigleyville presents mouthwatering burgers, fun-filled street dance parties and stunning scenic attractions. Explore the many attractions in Wrigleyville and bask in the buzz of the boundless energy of this neighbourhood. Wrigleyville features the historic Wrigley Field, the second oldest stadium in baseball history. So if you are a baseball fanatic, Wrigleyville is the ultimate place for you. With great weather, conducive for games, the Wrigley field is packed with passionate fans, popular delectable hot dogs and chilled beer during baseball season. Be it for business or leisure, Wrigleyville welcomes you into its bustling neighbourhood. Consider these recommended Airbnb vacation rentals specially tailored to your needs to catch your beauty sleep to keep up with the energy of Wrigleyville.
Things To Do
Chicago's Chinatown, IL: An Oriental Experience Not To Be Missed

As one of the largest and most vibrant ethnic neighbourhoods in the U.S, Chicago's Chinatown is worthy of a visit to get a sense of where the Chinese community in Chicago live, eat and work. While traditional urban Chinatowns in Manhattan, San Francisco, Philadelphia and Boston are fading due to gentrification and changing cultural landscapes, Chicago Chinatown's population reverses the trend with an increasing population. If you feel curious about this particular Chinatown, be sure to pop by when you are in Chicago! Read on to check out the must-eats and must-dos in Chicago's Chinatown.
Airbnb
10 Handpicked Airbnb Vacation Rentals In Burr Ridge, Illinois

‘’A very special place”, says the motto of the Village of Burr Ridge. Truly, this suburb of Chicago is a very special place with its large beautiful residences, rolling hills, nature parks, and warm locals. This town is also considered one of the wealthiest in Illinois. When in the area, you shouldn’t miss these attractions; Waterfall Glenn Forest Reserve, Salt Creek Woods, and Sagawau Canyon Nature Reserve – and get in touch with nature. Aside from the attractions, you should also take note of the amazing Airbnb vacation rentals they have here. In case you need help in choosing what to book, we have compiled a list for you below. Keep reading to learn more.
Airbnb
10 Best Airbnb Vacation Rentals Near Lincoln Square, Chicago

Lincoln Square is a family-friendly neighborhood of Chicago, located in the northern part of the city. This charming neighborhood is full of local shops, cafes, restaurants which hugely defines the concept of ‘Shop Local’. The locality had received its formal name in the year 1925. The charming neighborhood also has an interesting history of European settlers. The Swiss, English and German descendants had settled in this neighborhood and most of them were farmers. There are a number of iconic businesses, like the Budlong Brothers’ pickle factory, established in the 1800s here. Thus the area is also known as Pickletown after this famous business. A stay here promises a charming atmosphere, with a chance to explore its ethnic restaurants. Popular street fests like the Apple Fest and the Square Roots Music Festival are also celebrated here. Check out the list of best Airbnbs near Lincoln Square, Chicago for your next visit to the 'Windy City'.
Airbnb
Top 11 Airbnb Vacation Rentals In Glen Ellyn, Illinois

Glen Ellyn is located just west of Chicago and is the perfect place for a getaway from the city. Its incredible natural attractions include the Willowbrook Wildlife Center, which allows visitors to explore various types of habitats and terrains and catch sight of the animals which call them home. The landmark Lake Ellyn is also a great place to relax or join in some exciting outdoor activities. Meanwhile, golf lovers will be thrilled to visit the expansive Village Links golf course and enjoy a game on its beautifully manicured greens. If you're looking for an Airbnb vacation rental to stay in Glen Ellyn, keep reading!
Rent A Boat
Rent A Boat In Chicago, Illinois

The Windy City, Chicago, is one of the most populated and most popular cities in the U.S. With a rich history, beautiful geographic location and a culturally diverse population, Chicago attracts thousands of visitors each year. Museums, award-winning restaurants, craft breweries, bars, nightclubs, parks, sports arenas, shopping outlets, aquariums, art galleries and a ton of other attractions are on offer here. Whether you are in the city to check out The Magnificent Mile, take the Architecture River Cruise or take in panoramic views of the city from SkyDeck Chicago, you need a comfortable place to rest your head at the end of the day. Stay at a unique accommodation in the form of a houseboat and experience life on the water. To know more, check out our suggestions to rent a boat in Chicago, Illinois.

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Hotels In ( 10) Hotels With Free Parking ( 5) Hotels With Hot Tubs ( 4) Hotels With Water Parks ( 4) Cheap Hotels ( 3) Family Resorts ( 3) Historic Hotels ( 3) Hotels With Balcony ( 3) Hotels With Free Breakfast ( 3) Hotels With View ( 3) Lakefront Hotels ( 3) 2 Bedroom Hotels ( 2) Hotels With Airport Shuttle ( 2) Hotels With Kitchen ( 2) Hotels With Pools ( 2) Hotels With Smoking Rooms ( 2) Romantic Getaways ( 2) Spa Resorts ( 2) Staycation ( 2) Themed Hotels ( 2) Where To Stay ( 2) 5 Star Hotels ( 1) Adults Only Hotels ( 1) Airbnb ( 1) Eco Hotels ( 1) Family Friendly Hotels ( 1) Famous Hotels ( 1) Gay Friendly Hotels ( 1) Golf Resorts ( 1) Haunted Hotels ( 1) Hotels By The River ( 1) Hotels For Couples ( 1) Hotels With Early Check In ( 1) Hotels With Fireplaces ( 1) Hotels With Indoor Swimming Pool ( 1) Hotels With Kiddie Pools ( 1) Hotels With Outdoor Pools ( 1) Hotels With Parking ( 1) Hotels With Private Pool ( 1) Hotels With Restaurants ( 1) Hotels With Rooftop Bars ( 1) Hotels With Rooftop Pool ( 1) Luxury Hotels ( 1) Luxury Resorts ( 1) Party Hotels ( 1) Romantic Staycations ( 1) Ski Resorts ( 1) Treehouse Hotels ( 1) Unique Hotels ( 1) Wellness Retreats ( 1) Yoga Retreats ( 1) +46 more Show less

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Things To Do (87) Festivals (4) Indian Restaurants (4) Halal Restaurants (3) Kosher Restaurants (3) Rooftop Bars (3) Asian Restaurants (2) Attractions (2) Best Places To Live (2) Casual Restaurants In (2) Guide To (2) Romantic Getaways (2) Theme Parks (2) Airbnb Experiences (1) Bachelor Parties (1) Bachelorette Parties (1) Best Places To Visit (1) Brunch Buffets (1) Buddhist Temples (1) Car Rentals (1) Caving (1) Childrens Museums (1) Chinese Restaurants (1) Christmas Markets (1) Coffee Shops (1) Coolest Neighborhoods (1) Date Night Ideas (1) Day Trips From (1) Department Stores (1) Desserts (1) Dinner Cruises (1) Dive Bars (1) Famous Buildings (1) Fancy Restaurants (1) Farm To Table Restaurants (1) Food Markets (1) Fountains (1) Free Walking Tours (1) Gluten Free Bakeries (1) Halal Steaks (1) Happy Hour (1) Haunted Hotels (1) Haunted Places (1) Hiking (1) Hip Hop Bars (1) History Tours (1) Hotel Bars (1) Instagrammable Places (1) Italian Restaurants (1) Jazz Bars (1) Kid Friendly Restaurants (1) Korean Spa (1) Lakes (1) Live Music (1) Nightclubs (1) Non Touristy Things To Do (1) Oldest Restaurants (1) Outdoor Activities (1) Party Houses For One Night (1) Piano Bars (1) Places To Eat (1) Romantic Places (1) Rooftop Restaurants (1) Shopping In (1) Shopping Malls (1) Skateparks (1) Soup Restaurants In (1) Spots For Biryani (1) Spots For Halal Pizza (1) Street Food (1) Things To Do Alone (1) Things To Do At Christmas (1) Things To Do This Weekend (1) Viator (1) Weekend Getaways (1) What To Buy (1) +71 more Show less

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