Hotels near Wintrust Arena, Near South Side

These Wintrust Arena insights are based on real traveler data from Expedia, aggregated using AI to help you plan your trip. Updated: August 29, 2026.

Top reasons to visit Wintrust Arena

• Exciting Sports Events: Catch thrilling hockey games and other live sports at Wintrust Arena.
• Informative Arena Tours: Take a guided tour to learn about the history and operations of the arena.
• Vibrant Arts Scene: Explore nearby theaters and art venues for engaging performances and exhibits.
• Stunning City Views: Enjoy scenic walks along S Franklin St, showcasing the iconic Chicago skyline.
• Diverse Accommodation Options: Choose from a range of hotels, including pet-friendly and LGBTQIA-friendly options.

Find great hotels near Wintrust Arena

Looking for the perfect place to stay during your visit to Wintrust Arena in Chicago? You'll find a variety of hotel options nearby, catering to both business travelers and leisure seekers. From pet-friendly accommodations to LGBTQIA welcoming environments, the area offers a range of facilities to enhance your stay. Discover the closest hotels to Wintrust Arena for a convenient and enjoyable experience in the heart of the city.

• Congress Plaza Hotel: A 3.5-star hotel with a guest rating of 8.0, Congress Plaza Hotel is ideally situated one mile from Wintrust Arena in a vibrant shopping district. This property is perfect for business travelers and shoppers alike, offering convenient access to nearby retail options. Guests appreciate the hotel’s blend of classic architecture and modern amenities, making it a comfortable yet practical choice. It features spacious rooms, a well-equipped business center, and a welcoming atmosphere that encourages both relaxation and productivity.
• Hyatt Regency Chicago: With a 4-star rating and an impressive guest rating of 9.4, Hyatt Regency Chicago is located two miles from Wintrust Arena in the heart of the city. This hotel offers a unique city-themed experience, combining business travel with a touch of nature. Guests can enjoy outdoor amenities, including a terrace that allows them to soak in the city vibes. The property emphasizes wellness, providing a tranquil escape from the urban bustle with its serene surroundings and thoughtfully designed spaces, making it an excellent choice for those looking to rejuvenate during their stay.
• LondonHouse Chicago, Curio Collection by Hilton: A luxurious 4.5-star hotel with a stellar guest rating of 9.4, LondonHouse Chicago is two miles from Wintrust Arena and is located in a prime shopping district. This property is ideal for travelers seeking a luxury, spa-themed experience, complete with full-service spa offerings such as aromatherapy and hydrotherapy treatments. Guests can unwind by the pool or indulge in manicures and hot stone massages, all within a sophisticated atmosphere that exudes elegance. Its central location ensures that shopping and dining are just steps away, making it a perfect retreat.

Where to stay near Wintrust Arena

Visitors to Wintrust Arena will discover a vibrant blend of urban energy and scenic charm. Stroll along S Franklin St to soak in the stunning Chicago skyline, or explore nearby neighborhoods that exude a friendly atmosphere perfect for families. Don’t miss the romantic ambiance of the local parks, where you can unwind and enjoy the city's dynamic views. Whether you seek business or leisure, the area offers something for everyone in a welcoming environment.

• Chicago: As one of the most vibrant metropolises in the United States, Chicago is a hub of culture, history, and entertainment. With Wintrust Arena located right in the heart of the city, visitors can enjoy a variety of activities year-round. From shopping in bustling districts to catching a live show at a local theater, there’s something for everyone. The city is also home to iconic landmarks such as the Chicago Sports Facility Stadium and beautiful urban parks, making it a perfect destination for family outings and outdoor adventures.
• Downtown Chicago: Located a mere 2 miles from Wintrust Arena, Downtown Chicago is a bustling neighborhood that embodies the essence of urban living. Known for its impressive skyline and vibrant energy, this area attracts travelers seeking family-friendly activities, outdoor experiences, and city-themed adventures. Visitors can explore shopping areas, world-renowned theaters, and enjoy the proximity to major attractions like urban parks and sports facilities. The atmosphere in Downtown Chicago is lively, making it an ideal spot for both relaxation and excitement.
• Near South Side: Nestled around Wintrust Arena, Near South Side is a dynamic neighborhood that experiences seasonal visitor traffic, peaking during spring and summer months. This area is perfect for families and those seeking entertainment or business opportunities. With its array of arena facilities, shopping areas, and educational venues, there’s no shortage of activities to engage in. Local landmarks such as the convention center and event conference venues add to the rich tapestry of experiences available, making it a vibrant place to explore.

Things to do near Wintrust Arena

When visiting Wintrust Arena in Chicago, don't miss out on exciting activities such as catching a thrilling hockey game or taking an informative arena tour. The surrounding area also offers a vibrant arts scene and engaging theater performances, providing plenty of entertainment options to enhance your experience. Whether you're an avid sports fan or a culture enthusiast, Wintrust Arena and its vicinity have something for everyone.

Shopping

At Wintrust Arena, you'll find nearby shopping options such as the historic State Street, famous for its unique boutiques and iconic department stores. If you're up for a drive, head to Woodfield Mall, 30 miles away, offering a vast selection of shops and dining experiences.

Recreation

Experience the luxury of Chevy Chase Country Club with its exquisite amenities and serene golf courses, perfect for relaxation. Alternatively, Ravinia Green Country Club offers a tranquil environment for leisure and socializing. Broken Arrow Golf Club, known for its picturesque landscapes, provides an ideal setting for rejuvenation.

Adventure

Wintrust Arena hosts exhilarating events such as concerts, sports games, and family shows. Experience the thrill of live performances, cheer for your favorite teams, or enjoy engaging entertainment options, all within a vibrant atmosphere that captures the spirit of Chicago.

Nightlife

The nightlife around Wintrust Arena is vibrant and exciting. Enjoy live music at nearby venues like Reggies or grab a drink at the lively Bar Louie. For a fun night out, check out the local dance clubs or catch a show at the arena itself.

Booking tips and Expedia advantages for Wintrust Arena

• The most and least expensive months on average to stay in a hotel: The cheapest months to stay around Wintrust Arena are December to February, where the prices are slightly lower. This is in comparison to June and September to October, where prices are slightly higher.
• The most and least expensive days on average to stay in a hotel: The least expensive day to stay around Wintrust Arena is Monday. The most expensive day to stay around Wintrust Arena is Saturday.
• Find cheap hotels on Expedia: Utilize Expedia’s search tool to customize your preferences, such as your budget, desired location, and preferred hotel type. To discover the best prices and offers, arrange the price filter from lowest to highest.
• Consider bundling your trip: You can save money by combining your hotel stay near Wintrust Arena with your flights and activities through an Expedia package deal.

Find the best attractions near Wintrust Arena

When visiting Wintrust Arena in Chicago, you'll find a variety of attractions to explore, including urban parks, striking skyscrapers, and historic buildings. These points of interest cater to those seeking cultural experiences, family-friendly activities, and the vibrant city life that Chicago is known for. Be sure to take some time to enjoy the local scenery and immerse yourself in the rich history of the area.

• Michigan Avenue: Known as the Magnificent Mile, Michigan Avenue offers a vibrant city atmosphere filled with world-class shopping, dining, and iconic architecture. Stroll along this bustling street to experience the heart of Chicago's urban culture.
• Grant Park: Often referred to as Chicago's Front Yard, Grant Park is a sprawling urban oasis. It features beautiful gardens, playgrounds, and open spaces perfect for family picnics, outdoor events, and leisurely walks amid stunning city views.
• Chicago Riverwalk: This scenic waterfront promenade invites visitors to explore the beauty of the Chicago River. Enjoy walking, dining, or simply relaxing by the water while taking in breathtaking views of the city's skyline and vibrant atmosphere.

Best time to go to Wintrust Arena

The best time to visit Wintrust Arena is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	25.7°F (-3.5°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low
February	27.0°F (-2.8°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low
March	37.0°F (2.8°C)	Light Rain	Mostly Cloudy	Average	Average
April	46.0°F (7.8°C)	Light Rain	Mostly Sunny	Slightly Low	Average
May	57.0°F (13.9°C)	Light Rain	Mostly Sunny	Average	Average
June	67.3°F (19.6°C)	Light Rain	Mostly Sunny	Average	Slightly High
July	73.4°F (23.0°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	73.0°F (22.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
September	67.1°F (19.5°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
October	54.9°F (12.7°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	42.3°F (5.7°C)	Light Rain	Mostly Sunny	Average	Average
December	33.1°F (0.6°C)	Light Rain	Mostly Cloudy	Average	Slightly Low

The nearest major airports for your trip to Wintrust Arena

Traveling to Wintrust Arena in Chicago is convenient with access to three major airports. Chicago O'Hare International Airport (ORD) is 17 miles away, with nearby hotels like the 4.5-star Loews Chicago O'Hare Hotel and the 4-star Hyatt Regency O'Hare, both 2 miles from the airport. Chicago Midway International Airport (MDW) is only 8 miles away, featuring luxury accommodations such as the 5-star Nobu Hotel Chicago, located 8 miles from the airport. For those considering Milwaukee's General Mitchell International Airport (MKE), located 77 miles away, notable hotels include the 4.5-star Pfister Hotel and Potawatomi Hotel & Casino, both 6 miles from the airport. Each airport offers accessible transportation to the hotels.