Chicago invented the skyscraper, and nowhere is that legacy more enjoyable than on a rooftop with a cocktail in hand. From sweeping views of Lake Michigan to sightlines toward Wrigley Field and the city’s celebrated architecture, Chicago’s rooftop bars pair spectacular panoramas with thoughtful drinks and shareable plates. Many venues offer enclosed or retractable-roof spaces, so you can visit year-round—sunny summer evenings and snowy winter nights alike.
How these picks were chosen
Every spot was selected and reviewed by Condé Nast Traveler editors and a local contributor who visited in person. Selections reflect a mix of price points and styles and take into account standout food and drink, service, atmosphere, location, and operational practices. The list is updated as new rooftops open and existing venues evolve.
Roof on TheWit
Located on the 27th floor of theWit Chicago, Roof on TheWit is a high-energy, design-forward room with floor-to-ceiling windows and a retractable roof that makes the space welcoming in every season. The sound and lighting are part of the experience—think pulsing beats, an LED wall, and graphic floor tiles—while the drink program leans seasonal and inventive. Summer cocktails have included playful, tropical-forward creations such as the State & Rare (banana‑infused tequila, orange, and orgeat) and the Magnificent Spritz (kiwi-and-apple–infused gin with elderflower and cucumber).
The kitchen under chef Armando Diaz focuses on colorful, globally inspired plates with local sourcing and seasonal twists. Highlights to try: the Spring Tostada with spicy pea purée and crispy maitake; lobster and shrimp tacos dorados with avocado crema; and a tavern-style zucchini pizza with roasted corn and tomatoes. For something sweet, the white chocolate–potato-chip–macadamia cookies with a roasted pineapple milkshake are a memorable finish.
Upstairs at the Gwen
Perched atop the Gwen hotel, this terrace offers a relaxed escape from downtown while keeping city views in sight. Comfortable lounge seating, greenery, and upbeat music create an inviting atmosphere for afternoon drinks or evening gatherings. The terrace is programmed for year-round fun—winter offerings can include fire-pit seating and seasonal activities like casual curling, paired with hot chocolate or warming cocktails.
The bar features handcrafted cocktails and a curated wine list by the glass and bottle. The food menu is approachable and shareable: garlic shrimp with Spanish chorizo, beef tenderloin sliders, and a hummus with pine nuts and sumac make great starters. For mains, choose the salmon or the house hand-cut pappardelle with pecorino and basil. Finish with the chocolate chip cookies made with brown butter and caramel chips.
Whether you want a lively, music-forward scene or a more lounge-like terrace with cozy winter options, Chicago’s rooftops offer views and menus to match nearly every mood and season.
