The 8 BEST Hotels for Boys Trips in Chicago 2026
Discover the top hotels in Chicago that are perfect for an exciting and memorable boys trip. Finding the perfect hotel for a boys trip in Chicago can be a daunting task, as not every accommodation caters to the unique needs of a group seeking adventure and camaraderie. This list curates some of the best options that combine comfort, fun, and accessibility, ensuring an unforgettable getaway.
Godfrey Hotel Chicago
127 West Huron, at LaSalle
Offers breathtaking skyline views from a stylish rooftop bar, perfect for an unforgettable boys trip. Imagine sipping cocktails with your friends while taking in the stunning Chicago skyline from the IO Urban Rooftop bar. The atmosphere buzzes with excitement, making it the ultimate spot to kick back after exploring the city. Each contemporary room, equipped with a wet bar, sets the stage for relaxed evenings of camaraderie and laughter. Don’t miss out on this experience, book your stay at Godfrey Hotel Chicago today and elevate your trip to the Windy City.
Hotel Lincoln
1816 N Clark Street
Boasts a rooftop bar with stunning skyline views, perfect for unforgettable nights with your crew. Imagine sipping drinks with your friends while the Chicago skyline glimmers in the background. Hotel Lincoln sits conveniently near Lincoln Park, making it easy to explore the city's vibrant attractions by day and unwind in style by night. The chic, modern rooms blend historic charm with everything you need, ensuring your stay is both comfortable and memorable. Don't miss out on this prime spot to elevate your boys trip, book your stay now and dive into the heart of Chicago.
Freehand Chicago
19 East Ohio Street
Delivers a vibrant blend of comfort and exceptional dining for the ultimate boys trip experience in Chicago. With its unique boutique atmosphere in the heart of River North, this hotel invites your crew to unwind in style. Versatile room options cater to all budgets, whether you want a private space to regroup or a shared room for camaraderie. The on-site restaurant serves up mouthwatering dishes that fuel your adventures, while the nightlife scene keeps the energy high. Don’t wait to transform your boys trip into an unforgettable getaway; book your stay at Freehand Chicago today.
The Chicago Hotel Collection Wrigleyville
3475 N. Clark St.
Brings excitement and camaraderie just steps from Wrigley Field. This hotel embodies the spirit of a boys trip with its welcoming shared lounge, where laughter and stories flow freely. Picture your crew gathering here after a day of exploring Chicago, sharing unforgettable moments in a space designed for socializing. With Lincoln Park Zoo and 360 Chicago nearby, adventure is always within reach. Make your trip legendary by booking your stay at The Chicago Hotel Collection Wrigleyville now.
Hotel Saint Clair - Magnificent Mile
162 East Ontario Street
Boasts stunning city views that elevate your boys trip to unforgettable heights. Imagine sipping drinks with your crew while gazing at the unforgettable skyline from your room at Hotel Saint Clair. Located just steps from the buzzing nightlife of the Magnificent Mile, this vibrant spot captures the excitement of Chicago's energy. The unique European-style charm adds a layer of sophistication that makes every moment feel special. Don't miss out on the chance to create memories in a place that embodies everything your boys trip should be, book your stay now.
Travelodge by Wyndham Downtown Chicago
65 E Harrison St
Boasts a vibrant location just steps from Millennium Park and a variety of dining options. This is the backdrop for unforgettable memories with friends as you dive into Chicago's nightlife. Explore the diverse culinary scene right around the corner, fueling your adventures with local flavors. After a night out, return to spacious family rooms designed for relaxation and sharing stories of the day. Don’t miss out on this chance to make your boys trip legendary, book now and experience the pulse of the Windy City.
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St
Brings together adventure and relaxation in the heart of Chicago. With state-of-the-art fitness facilities, this hotel keeps the adrenaline pumping for any group ready to tackle the Windy City. After an exhilarating day of exploring, indulge in gourmet dining options that elevate your culinary experience, making every meal a highlight of your trip. The vibrant atmosphere and spacious family rooms create the perfect backdrop for bonding, laughter, and unforgettable memories with friends. Don't miss out on the chance to make your boys' trip truly special, book your stay today.
Millennium Knickerbocker Chicago
163 East Walton Place
Delivers unforgettable nights with classic cocktails and the iconic Crystal Ballroom. Gather your crew at the Martini Bar, where the 1920s come alive with expertly crafted drinks that set the stage for laughter and camaraderie. The Crystal Ballroom beckons for epic celebrations, providing a backdrop of elegance that transforms any night into a memorable event. After indulging in farm-to-table delights at NiX, retreat to upscale rooms featuring plush bedding and rainfall showers to recharge for the next adventure. Book now and elevate your boys trip to Chicago into an experience you'll never forget.
Frequently Asked Questions
What neighborhoods are best for boys trips in Chicago?
For a fun and vibrant experience, consider staying in River North or Wicker Park. These neighborhoods offer a mix of nightlife, dining, and easy access to attractions.
Are there hotels in Chicago that offer group accommodations?
Yes, many hotels in downtown Chicago have spacious suites or connecting rooms that can accommodate larger groups. Look for hotels that specifically mention group bookings.
What amenities should I look for in a hotel for a boys trip?
Look for hotels that offer a fitness center, bar or lounge, and possibly a rooftop deck. These amenities can enhance relaxation and socializing during your stay.
Can you recommend hotels near sports venues in Chicago?
Consider staying at the Crowne Plaza Chicago West Loop or the Hyatt Place Chicago/South Loop. Both hotels provide easy access to Wrigley Field and United Center.
Are there any hotels in Chicago with great views of the skyline?
The LondonHouse Chicago and the InterContinental Chicago Magnificent Mile both offer stunning skyline views. These locations are perfect for enjoying the cityscape.
What hotels are near popular breweries in Chicago?
The Hilton Garden Inn Chicago Downtown/Magnificent Mile is a great option. It is close to several breweries, including Goose Island and Revolution Brewing.
Which hotels are closest to Chicago's nightlife?
Stay at the Ace Hotel Chicago or the Thompson Chicago to be near popular nightlife spots in River North and the Gold Coast. Both provide a stylish atmosphere and easy access to clubs and bars.
Are there hotels with recreational activities nearby?
The Marriott Marquis Chicago is near the McCormick Place Convention Center, which hosts various events and has recreational facilities. Check for special events during your stay.
What are the best hotels for outdoor activities in Chicago?
The Hotel Lincoln is ideal as it is close to Lincoln Park and the waterfront. This location offers plenty of outdoor activities, including biking and walking along Lake Michigan.
Can you suggest hotels with easy access to public transportation?
The Hyatt Regency Chicago and the Palmer House Hilton both have convenient access to the CTA trains and buses. This makes it easy to explore the city without needing a car.
