Chicago offers a diverse and exciting culinary landscape, making it an excellent destination for group dining. From iconic American comfort food like deep dish pizza and hot dogs to sophisticated Italian, Mediterranean small plates, and upscale steakhouses, there is something for every palate. The city's food scene thrives in energetic neighborhoods such as River North, known for its chic and sophisticated options, and West Loop, a true culinary hotspot. Gold Coast also provides luxurious settings for group meals. While many establishments can accommodate groups, securing reservations, especially for tables of six or more, is often essential to ensure a smooth dining experience.
How we picked these
The recommendations in this guide are directly aggregated from real Anywayr (formerly Travelry) trip recommendations, reflecting what our users have enjoyed most in Chicago. We prioritize venues and neighborhoods that have been frequently mentioned across past trips, ensuring that our picks are tried-and-true favorites. The mention count for each venue serves as a strong indicator of its popularity and consistent appeal among travelers.
Eat smart as a group
When dining with a group in Chicago, a little planning goes a long way. For tables of six or more, making reservations well in advance is highly recommended, especially for dinner or during peak tourist months like March, May, and June. Many restaurants in popular areas like River North and West Loop can fill up quickly. When it comes to splitting bills, confirm the restaurant's policy beforehand. Some establishments prefer a single payment or can only split checks evenly, while others are more flexible.
Consider your group's interests and the time of day when planning your meals. For breakfast or lunch, casual cafes and American diners are abundant. Dinner often calls for more upscale or specialized experiences. Group-friendly neighborhoods like River North and West Loop offer a high concentration of diverse dining options, making it easy to hop between venues. It is generally advisable to avoid areas like the Far South Side, West Garfield Park, and Englewood, which have limited tourist infrastructure and higher crime rates.
Pacing your meals is also key for a multi-day trip. Mix casual, quick bites with more leisurely, sit-down dinners. For instance, a classic Chicago hot dog for lunch can be followed by a sophisticated Italian dinner. This approach allows your group to experience a wider range of Chicago's culinary offerings without feeling rushed or overscheduled.
Our picks
Below, you will find a curated selection of Chicago's best dining venues for groups. These establishments have been chosen based on their popularity among Anywayr users and their suitability for various group sizes and preferences.
Booking tips for large tables
For groups requiring larger tables, it is always best to call the restaurant directly rather than relying solely on online booking platforms, as they may have more availability or specific seating arrangements not listed online. Be prepared for potential deposit policies, especially for private dining rooms or during busy periods. Some upscale restaurants might require a credit card to hold a reservation, with a cancellation fee if not adhered to. Additionally, many establishments automatically apply a gratuity of 18-20% for parties of six or more. Always confirm this policy when booking or upon arrival to avoid any surprises.