Dine in Summer Style at These Waterside Restaurants

Summer in Chicago is the best time of year to dine with a waterside view overlooking sea-sized Lake Michigan, drinking in the panoramic views as you simultaneously drink wine, cocktails and beer. Whether it’s a skyscraper-sized view or a casual cafe, these are some of your best options for beachy views and waterside vibes in the city this season. 


Caffe Oliva
Caffe Oliva

The Signature Room: Chicago’s most iconic location for dining with a soaring view is undoubtedly The Signature Room. Unless you’re paralyzed by a fear of heights, that is, because in order to get to the restaurant you’ll need to ascend an elevator to the 95th floor of the John Hancock. Once here, you’ll savor modern American cuisine with a seasonal tilt, plus craft cocktails, wine and beer. No matter where you’re seated, you’ll be rewarded with majestic, awe-inspiring views of Lake Michigan and the skyline. The best seats in the house, though, are the ones perched up against the north-facing glass wall, which affords a stunning vista of Chicago’s beach-lined north side.

Cite: One of the most criminally underrated restaurants when it comes to sky-high dining in Chicago, Cite gets you so close to the lake you may actually feel like you could fall in. Located on the 70th floor  of Lake Point Tower, the only skyscraper east of Lake Shore Drive, and just in front of Navy Pier, the soaring restaurant has extraordinary views from every angle. The seafood, steaks, cocktails and tasting menus aren’t too shabby, either. Using French techniques and a seasonal mentality, the restaurant features ever-changing dishes like lobster tail with butter gnocchi, sesame-crusted Alaskan salmon, venison strip loin with poached pear and rack of lamb with ratatouille. 

Caffe Oliva: When it comes to beachy dining in the city, it doesn’t get much better — or beachier — than Caffe Oliva. This bright and sunny cafe is literally located right on Ohio Street Beach alongside Navy Pier, providing a warm, relaxing vibe to your patio dining experience. This year’s menu is better than ever, featuring an eclectic lineup of shareable plates like Greek bruschetta, fried calamari with lime aioli, coconut shrimp, margherita flatbreads, blackened whitefish with tzatziki and a slew of sandwiches and burgers. There’s also a kids’ menu, desserts, brunch and a ton of cocktails. Keep the group party going with one of Caffe Oliva’s fish bowls, designed to satisfy a thirsty group with potions like the “Finding Nemo”: blueberry vodka, pineapple juice, sour, fresh lemon juice and Swedish fish.

Pinstripes: If the idea of dining and drinking at a bowling alley sounds like a joke to you, then clearly you haven’t spent any time at a Pinstripes. This beloved mini-chain is popular for good reason, and their Streeterville location (the only one in city limits) backs it all up with the added bonus of being right on the Ogden Slip harbor, with a lengthy fire pit-lined patio overlooking the lake. In addition to bowling and bocce inside, Pinstripes sets itself apart as a restaurant destination in and of itself, with casual yet inventive Italian food that’s great both for snacking-while-gaming and for a leisurely meal al fresco or indoors. 

Cafe Spiaggia: For upscale Italian fare with an equally impressive vista, don’t miss Cafe Spiaggia. Or really if you’re feeling decadent, it’s even more upscale sister restaurant Spiaggia. But due to its more accessible offerings, Cafe Spiaggia is certainly an easier stopover for a quick lunch with a sensational overlooking the top of the Magnificent Mile and Oak Street Beach. The restaurant offers a contemporary, elegant take on classic Italian cuisine, making for a fine meal while nestled along the windows above one of the most famous shopping streets in the country.