Chicago is a popular destination for groups, with Anywayr (formerly Travelry) users typically traveling in parties of three for about seven days. Peak months for group visits include March, April, May, and June. Top interests for these groups are Nightlife & Entertainment, Adventure & Outdoor Activities, Cultural Experiences, and Beach & Water Sports. Group lodging in Chicago often means securing a larger rental property, which provides more communal space and shared amenities compared to booking multiple hotel rooms. Neighborhood choice significantly impacts the group experience, affecting walkability, access to attractions, and parking availability.
What to look for in a group stay here
When selecting a group stay in Chicago, consider the actual number of bedrooms versus the total 'sleeps' capacity. While a property might sleep 16, it could have fewer private bedrooms, meaning some guests will use common areas for sleeping. Ensure there are enough bathrooms for your group size to avoid morning rush hour. Common pitfalls for groups include underestimating travel times between neighborhoods and not having enough shared living space for everyone to relax comfortably.
Chicago's neighborhoods offer distinct vibes and amenities. River North is chic and energetic, ideal for upscale nightlife, cocktail bars, and fine dining. West Loop offers an industrial chic, trendy atmosphere, known for its foodie scene and live music. Lincoln Park is green and family-friendly, suitable for outdoor activities and shopping. The Gold Coast provides a luxurious, historic setting, great for beach access and nightlife. Lakeview is friendly and lively, known for sports bars and casual pubs. The Loop is monumental and cultural, perfect for architecture and cultural experiences. For groups prioritizing safety and tourist infrastructure, it is advisable to avoid areas like the Far South Side, West Garfield Park, and Englewood.
Our picks
Anywayr has curated a selection of top-rated group stays in Chicago, chosen for their capacity, amenities, and locations that cater to various group interests. These properties offer a range of options for your next group adventure.
Booking tips for larger groups
Booking a large group stay requires careful planning. Properties for bigger groups often come with higher security deposits, so factor this into your budget. Always review cancellation policies thoroughly, as terms can be stricter for larger rentals. Discuss payment splitting arrangements with your group and the property owner in advance to ensure smooth logistics. Given Chicago's popularity, especially during peak travel months from March to June, booking your group accommodation well in advance is highly recommended to secure your preferred property and location.
