Neighborhood Guide
Streeterville is shaped by the water. The neighborhood sits between the river and the lake, giving weekends a destination feel while keeping everything close and accessible.
Book Your CharterStaying in Streeterville keeps the weekend centered around the waterfront. Sable Hotel Navy Pier, Loews Chicago, and Embassy Suites place guests within walking distance of the lake, river access, and major gathering points. Hotels here often function as hubs for both daytime plans and evening meetups.
Streeterville works well for weekends built around the water. Days often revolve around lakefront walks, boat access, and open air settings before transitioning into relaxed meals and rooftop drinks.
Pinstripes, Shore Club, and Robert's Pizza provide flexible gathering spots that accommodate groups without rushing turnover. Evenings tend to stay scenic rather than nightlife driven, allowing groups to stay together and keep plans fluid.
Wedding weekends in Streeterville lean scenic and organized. Welcome parties and post ceremony gatherings often take advantage of the waterfront, with venues like Sheraton Grand, Chicago Yacht Club, and Offshore Rooftop serving as natural anchors.
Local wedding planners frequently coordinate multi day events in this area, keeping ceremonies, receptions, and social gatherings within close proximity for out of town guests.
Holiday weekends amplify Streeterville's energy without changing its layout. Fireworks, seasonal programming, and waterfront events draw visitors toward Navy Pier and nearby hotels.
Event calendars hosted by Loews Chicago and broader city programming promoted through Choose Chicago help define the seasonal rhythm and keep visitors informed during peak weekends.
Streeterville's dining scene is designed around comfort and views. Restaurants and lounges prioritize space and scenery, making them well suited for groups.
The neighborhood's defining feature is Navy Pier. Lakefront paths, boat access, and waterfront venues shape much of the weekend flow. Much of Streeterville's activity centers around the pier, supported by nearby hotels and lakefront programming.
Estimated travel times to our harbor locations. We recommend arriving 30 minutes before your scheduled departure.
3155 S. Lake Shore Dr., Chicago
1559 S. Lake Shore Dr., Chicago
Book a private yacht charter from Streeterville and experience the Chicago skyline like never before.