Chicago's best al fresco dining experiences

New this summer, Four Seasons Hotel Chicago has a 52-foot Absolute yacht available for what are sure to be the most luxurious al fresco private dinner parties in the city. Hotel guests can charter the yacht for cruises along the Chicago River and Lake Michigan for parties of up to 12 people, with Adorn's new executive chef Richie Farina serving customised menus with his signature whimsical flair – definitely request the focaccia waffles topped with burrata and balsamic. The yacht docks in the heart of the city on the Chicago River and is bookable from June through September with a variety of curated culinary experiences, such as cocktail classes, sommelier-led wine tastings and sunset tasting menus. 

This whimsical, kaleidoscopic 10,000-square-foot playground for adults is located above The Second City comedy club, with some of the best views of the city's famous skyline. Pause between playing super-sized versions of Jenga and Connect Four to appreciate the panorama whilst sipping on refreshing large-format cocktails. To eat, there's crave-able finger food like sliders, footlong hot dogs, mozzarella sticks and dessert tacos filled with creamy cheesecake. No matter your age, Utopian Tailgate will make you feel like a kid again. 

Family-friendly Roots Pizza specialises in Quad Cities-style malted-crust pizza, with a wide array of toppings, including homemade mozzarella. Their South Loop location is their newest and largest, with a fully-retractable glass rooftop on their second-floor atrium, which seats up to 100 guests. Everything from heaped bowl salads – a sleeper hit – to pizzas is totally customisable so you can build your own perfect meal whatever your preferences or dietary restrictions may be. There are always a few local chef collaboration speciality pizzas on the menu and a wide array of Midwestern beers on tap, while multiple flat-screen TVs and hearty food make this a favourite place for game day too. 

Whether you prefer your seafood raw or gently grilled over charcoal, the menu and Chicago River views from RPM Seafood's 112-seat patio are sure to impress. The expansive seafood-friendly wine list is among the best in the city, including more than two dozen by-the-glass pours, along with an exciting list of white and red Burgundy for wine connoisseurs, rounded out with Bordeaux, super Tuscans and great value wines from around the world. You'll be tempted to order a bottle to accompany crab cakes, fish tacos and grilled mixed seafood presented tableside with a flaming flourish. Lunch here can easily become a leisurely three-hour affair. 

The open-air rooftop and convivial, casual style of dining at Bar Avec, now also open for lunch, is inspired by the seashores of Spain and Portugal, but located in the heart of the city in River North, eight floors above sister restaurant Avec. James Beard award-winning Chef/Partner Paul Kahan lightens the rooftop menu with vibrant crudos, refreshing salads and tabbouleh paired with fruity cocktails and crisp wines. Don't fret – you can still order Avec's famous chorizo-stuffed bacon-wrapped medjool dates and shawarma fried chicken too. If you plan to walk in, just check on social media first to ensure they aren't closed for a private event. 

The lushly landscaped patio at Tzuco seats 50, with bright fuchsia bougainvillea spilling over the cantilevered roof, which can be easily closed should an occasional rain shower pass through. Chef/Partner Carlos Gaytán moved to Chicago from Guerrero, Mexico and a decade ago, he became the first Mexican chef to receive a Michelin star. A few of his signature dishes include squid ink black ceviche, guajillo-roasted octopus with salsa macha and braised lamb neck barbacoa. Monday through Friday the happy hour menu is a great deal too, with margaritas, Mexican negronis, cochinita pibil tostadas and guacamole for $10 apiece. 

The prettiest patio in the trendy Fulton Market district is this Italian-Croatian restaurant by Top Chef champion Joe Flamm. Rose Mary is named after his grandmothers, as well as the herb rosemary, native to the rocky regions of the Mediterranean and Adriatic from where Flamm draws inspiration. There's ample shade under Rose Mary’s striped umbrellas to keep diners cool on the 32-seat patio while they enjoy peka-style octopus, zucchini fritters and tuna crudo with a smattering of crispy capers. Flamm blends timeless Italian recipes with the bold, bright flavours found in Croatian cuisine, like gnocchi with beef cheek pašticada and Croatian paški sir sheep's milk cheese. 

The 72-seat veranda at Taureaux Tavern in the South Loop offers French-American bistro cuisine with great people watching. Summer favourites include pan-roasted branzino with caper meuniere sauce and grilled pork chop with corn, cherry tomatoes and mint. The best dessert on the menu is the light and boozy Manhattan trifle with Buffalo Trace pastry cream, Luxardo cherries, almond cake and whipped cream. Plus, the patio is dog-friendly; there's even a canine menu for four-legged guests.