Offshore

If you're up for the scenic walk down Navy Pier, Offshore, the world's largest rooftop, according to Guinness World Records, awaits at the end. The 36,000-square-foot, all-seasons bar and lounge offers sweeping skyline and lake views that you won't find anywhere else in the city.

The vibe: Twinkling string lights illuminate the outdoor gaming area, where guests can play bags, jumbo Jenga and Connect 4. The dress code is casual, and this is also a great place to start a night out on the town.

The food: Shareable plates like wings, fries, and roasted garlic and white bean dip are popular options for groups. The food is great for snacking, but if you're looking for a full-service meal, we recommend dining elsewhere as the prices are quite high ($28 for a burger and $32 for a poke bowl).   

The drinks: The cocktail list comprises a bevy of creative drinks that are perfect for summer. Sips like Not Your Mama's Fruitcake (vodka-infused tea, pomegranate juice, lemon juice, peach liqueur and passionfruit syrup) and It's Getting Mezzy (mezcal, triple sec, papaya puree and lime juice) are two of our go-tos. There are also a few non-alcoholic options, including THC-infused margaritas and mules.

Time Out tip: This is a prime spot to watch the Navy Pier fireworks, which happen every Wednesday and Saturday night throughout the summer.