Chicago’s waterfronts are some of the tastiest on earth! 

There is no shortage of amazing places to eat and drink in Chicago but if you go at the right time and the weather is amenable – as it so often is! – and you want to take it outside, well, you’re in luck. Lake Michigan is lined with beaches and those beaches, with their views across the Lake, are lined with drinking and dining destinations, all easy to get to thanks to the stunning Lakefront Trail.

At Oak Street Beach, arguably Chicago’s most famous stretch of sand under real palm trees, Oak Street Beach Food + Drink is the perfect spot for people-watching with beach-goers, Michigan Avenue shoppers and Lakefront fitness buffs parading for your enjoyment while you tuck into classic beach bar food and drinks and maybe a light game of Cornhole (you throw bean bags, it’s not hard) or sometimes even a DJ set.

Ladies who lunch (at Shore Club)

The latest addition to the beach foodie scene is Shore Club with its three unique spaces. There’s The Patio at Shore Club, a no-reservations open-air spot for lunch or dinner or just cocktails that’s a favourite with the beach crowd (don’t forget to check out their rotating schedule of specialty workshops, cooking classes and exhibitions of local art!)

The Restaurant at Shore Club is a little more formal and located indoors although those huge glass windows give a decidedly outdoorsy feel especially as the staff are done out in beach-inspired crisp whites as if you were on the sand in Mykonos or the South of France.

The Oasis at Shore Club takes things right back to casual with sunbeds and daybeds and signature cabanas looking onto the beach where you can order shared plates and mains, perfect for groups looking for a one-day getaway. Enjoy bubbles in the sun or go for the large-format Beach Party cocktail served in a giant copper pineapple or a flamingo. Just make sure you reserve in advance.

Theatre on the Lake

The newly done-up Theater on the Lake at Diversey Harbour is also in on the act with its Lakefront Restaurant serving up not only superb skyline views but a much-loved Midwestern menu. Steel arches, exposed brick and floor-to-ceiling windows overlook the Lake, bike path and Lincoln Park making it feel like you’re having your lunch in a lodge. And you can come as you are, whether you’re kitted out for a stroll along the bike path or done up for a pre-show cocktail. Locals love the slow-cooked brisket, the smoked Gouda and butterkase mac ‘n’ cheese maybe with one of their signature whiskey bacon steaks. To drink, try out one of their twists on the classic cocktail or explore the well-curated wine and craft beer menu.

Harbour views from inside Lakefront Restaurant

It may not be famous for its restaurants but Hollywood Beach, also known as Kathy Osterman Beach, after the LGBTQ activist, is where most gay travellers will find themselves at some time or another. The long sandy beaches feel more like Florida than Chicago and you could always take a picnic and then head over to nearby Andersonville, the very LGBTQ villagey area packed with a variety of places to eat, drink and be merry.

If you want to interact with the local canine population (as you might be missing yours) head to The Dock at Montrose Beach, a massive 3,000-square-foot beach bar with a dog-friendly policy. There you can tuck into burgers, tacos, salads and maybe even some live music (and some prime dog tickling) just a stone’s throw from the water and the nearby dog beach.

And be sure not to miss The Waterfront Café, tucked behind a charming old coach house at Berger Park on the Edgewater area. You might not find any sand but you are slap bang on Lake Michigan with a menu that includes crab cakes and walnut salad and a good selection of drinks making it an ideal, low-key way to end your beach bar crawl.