Chicago is an excellent choice for group travel, offering a diverse experience that appeals to many interests. Anywayr (formerly Travelry) data shows groups here typically consist of three people and stay for about seven days. Popular months for group trips include March, June, May, and April. Top interests among Anywayr users for Chicago include Nightlife & Entertainment, Adventure & Outdoor Activities, Cultural Experiences, and Beach & Water Sports, ensuring there is something for every member of your group.
Where to stay in Chicago as a group
When planning group lodging in Chicago, consider neighborhoods that balance convenience with your group's interests. River North is a primary stay area, known for its chic, energetic, and sophisticated atmosphere. It is best for upscale nightlife, cocktail bars, and fine dining. Another popular choice is Gold Coast, a luxurious and historic area perfect for beach access, dining, and nightlife. Both offer a central base with access to many of the city's attractions and a variety of dining options. Look for accommodations that provide ample common space for your group to gather.
Other neighborhoods worth considering for group stays include West Loop, an industrial chic and trendy culinary hotspot, ideal for foodies and live music. Lincoln Park offers a green, charming, and family-friendly environment, suitable for outdoor activities and shopping. Wicker Park and Lakeview also provide unique local experiences.
Groups should generally avoid areas like the Far South Side, West Garfield Park, and Englewood due to limited tourist infrastructure and safety concerns. These areas are not recommended for tourists. See our group-friendly stays
What to do as a group
Chicago delivers a rich array of experiences for groups, aligning with popular interests like Nightlife & Entertainment, Adventure & Outdoor Activities, Cultural Experiences, and Beach & Water Sports. Whether your group seeks vibrant evenings or daytime exploration, the city has options.
For dining, River North is a culinary hub. Groups frequently visit Portillo's Hot Dogs for American classics, RPM Italian, and Ema for Mediterranean cuisine. For a unique bar experience, Three Dots and a Dash offers a tiki atmosphere in River North, while Cindy's Rooftop in The Loop provides American fare with city views. In West Loop, Au Cheval is a popular American restaurant. Other River North favorites include Goddess and The Baker, The Hampton Social, and Lou Malnati's Pizzeria.
Beyond dining, Chicago's architecture is a major draw, particularly in The Loop. Groups can explore cultural experiences, enjoy outdoor activities, or relax by the water. Gold Coast offers opportunities for Beach & Water Sports. The city's diverse neighborhoods also provide unique shopping and entertainment options, from the independent boutiques of Wicker Park to the sports bars of Lakeview. Browse group activities
How long to stay
Anywayr's data indicates that the median trip length for groups visiting Chicago is seven days, with past trips ranging from six to seven days. A seven-day trip allows groups to fully immerse themselves in Chicago's diverse offerings, covering multiple neighborhoods, dining experiences, and activities without feeling rushed. Shorter trips, such as three or five days, are also feasible for groups focusing on specific interests like a culinary tour or a weekend of nightlife. However, a full week provides the most comprehensive experience. See sample itineraries
Plan your group trip
Chicago offers a dynamic and engaging backdrop for any group gathering, from friends exploring the city's nightlife to families enjoying its parks and cultural sites. With its distinct neighborhoods and a wide range of activities, planning your group trip to Chicago is straightforward. Anywayr can help streamline the process, ensuring your group makes the most of its time in this dynamic city. Start planning your Chicago group trip
