What to Do on a Weekend in Chicago’s Gold Coast

Making the most of your weekend is an absolute necessity, whether you reside in Chicago’s Gold Coast or are just in for a visit. The options for entertainment are endless, so we’ve put together an itinerary that’s sure to satisfy any city adventurer. Many of these locations are just a hop, skip, train ride, or cab ride away from the Gild apartments.

Morning Coffee

You’ll need fuel for the day ahead; start by grabbing a caffeinated buzz with Brazilian flair at PiniPico, and don’t forget to order their trademark pȃo de queijo – a cheese bread that warms your taste buds and pairs perfectly with a cup of joe. Or, try the breakfast empanada and a specialty latte – the cardamom rose matcha and honey bourbon both earn rave reviews and social media shoutouts galore. Check out our Gold Coast Guide on where to find the best coffee in the neighborhood.

Mid-Day Stroll through Lincoln Park

Head north with breakfast in hand to take a stroll through the urban respite that is Lincoln Park. You might even get to pet a few doggos on your journey! Enjoy a detour into Chicago’s beloved Lincoln Park Zoo if the weather permits. Or, hop over to the Lakefront Path to journey back into the Gold Coast, and enjoy the glistening skyline ahead of you – the perfect opportunity for curated selfies and Instagram stories.

Afternoon Tea at the Drake Hotel

Cross over at Oak St and kick off a high-end afternoon with tea at The Drake Hotel, a cherished tradition for over a century. You’ll be in good company – guests like Princess Diana and even the Queen have stopped by the Drake for a sip. Choose from over seventeen tea blends and dine on biscuits, finger sandwiches, and other delightful morsels from the three-tiered tea tray.

Skyline Views at the 360 Chicago Observatory

Zip on over to the Hancock Center and up to the 94th floor for the 360 Chicago Experience. Admire the scenic views from this spectacular perspective, and learn more about Chicago’s historical background and architecture. If you or your guests are in the mood to push the envelope, add on the TILT experience for a guaranteed thrill ride that no one will soon forget.

Shopping on Oak Street and Dinner at Gibson’s

While you work up an appetite for dinner, gather yourself and your crew for a shopping spree along Oak Street. Prada and Giorgio Armani are ready to welcome you inside, and Jimmy Choo and Louboutin will be happy to give your feet a luxurious place to rest.

After a full day of strolling in the city, treat yourself to a quintessential Gold Coast supper at Gibson’s Bar & Steakhouse. A Chicago staple that some think of as the Chicago steakhouse, Gibson’s provides a classic experience with an entertaining side of people watching. Eater Chicago says it’s known for ‘giant slabs of meat, giant slices of cake, and stiff martinis’. You’ve earned this glorious feast.

Evening at Second City Comedy Club

For the final cherry on top of your evening, laugh it up at Second City while catching one of the many side-splitting shows featured in their diverse lineup. Whether you’re seated for a revue, an improv jam, or stand-up, the stress of the workweek will be far behind you. Sunday Scaries, be gone!