On the Waterfront: Dining on Lake Michigan

Where to eat in Chicago to drink in views of Lake Michigan.

For those who prefer sandy stretches to complement their meal, you’re in luck. Chicago’s beaches are equipped with lakefront drinking and dining destinations which are easily accessible via the stunning Lakefront Trail, all offering impeccable views of Lake Michigan. Here’s a look at some of our favorite Lake Michigan dining destinations in Chicago.

Caffè Oliva, located at the foot of Navy Pier, offers Mediterranean-inspired fare, playful cocktails, and is tucked away on a beautiful stretch of the lakefront. If you’re hungry, I recommend their grilled calamari and splitting one of their flatbreads alongside a glass of wine. While there, make sure to venture through the serene refuge of the adjacent Milton Lee Olive Park where you can sprawl out on the grass and take in some of the best skyline views in the city. The park is named for the first African American awarded the Medal of Honor for his service in Vietnam. Prefer to dine indoors? Make sure to check out Riva Crab House on Navy Pier as it is the only Chicago seafood restaurant that is situated on the waterfront.

Situated upon the sandy shores of Chicago’s most famous Beach, Oak Street Beach Food + Drink is a lush oasis—complete with real palm trees!—offering some of the city’s best people watching including beach goers, Michigan Avenue shoppers, and the Lakefront fitness buffs. A casual destination, the menu here sticks mainly to classic drinks and beach bar food and offers complimentary cornhole play for those looking to be active in addition lively DJ sets on select nights.

The Lakefront Restaurant located inside the newly renovated Theater on the Lake, offers skyline views that pair perfectly with the lauded Midwestern fare. The steel arches, brick, and floor-to-ceiling windows that overlook the Lake, bike path, and Lincoln Park give the space an almost lodge-like feel. Whether you’re casual from a stroll along the bike path and want to pop in for lunch or are dressed to the nines looking to grab a pre-show cocktail, you can do both. It’s as fancy as you want to be. Can’t-miss menu items include the slow-cooked brisket, smoked Gouda and butterkase mac and cheese, and their signature whiskey bacon steak. The cocktail program here focuses on whimsical takes on the classics alongside a well-curated wine and craft beer selection.

The Dock at Montrose Beach is a sprawling, 3,000-square-foot beach bar offering up burgers, tacos, salads, and live music just a stone’s throw from the water. Another perk is that it’s also dog-friendly, so it’s a popular stop for locals after bringing their canine companions to the nearby dog beach.

Made up of three unique spaces, Shore Club is a newcomer to the lakefront dining destination scene. The Patio at Shore Club features lunch and dinner service on a first-come-first-serve basis. The open-air patio is accessible to beach patrons and is the hotspot for those looking to unwind with a quick bite and a cocktail after a long day on the beach. The informal and comfortable atmosphere features a rotating schedule of specialty workshops, cooking classes, and local art exhibitions. The Restaurant at Shore Club offers an elevated food menu in a covered, open air environment. Boasting large glass windows and an attentive staff dressed in beach-inspired crisp whites with splashes of teal, The Restaurant at Shore Club makes visitors feel as if they are vacationing on a far-off coastal beach. At The Oasis at Shore Club, guests have the opportunity to relax and enjoy the beach views from a sunbed, daybed or a signature cabana. The menu offers a beautiful array of shared plates and large format options, perfect for groups looking for a one-day getaway. Guests can soak up the sun and indulge in some bubbles or go for the large-format Beach Party cocktail that’s served in a giant copper pineapple or a flamingo. Note: reservations are required for The Oasis at Shore Club.

Just a bit further north, tucked behind a charming old coach house in the Edgewater neighborhood, you’ll find The Waterfront Cafe. While there’s no sand, per se, you’re literally right on Lake Michigan. Food offerings range from crab cakes to apple walnut salad and they offer a roster of drinks making it an ideal, low key way to end your beach bar crawl.