The Best Five-Star Hotels in Chicago, Illinois

Chicago’s only tri-level rooftop is a sight to behold. Located where Fort Dearborn once stood, the building itself is a designated Chicago landmark. Roman figures are engraved into the stone facade, but the interior is fully upgraded with high design and an elegant feel. The hotel is situated on a corner of the Michigan Avenue Bridge, leading to Hubbard Street and Navy Pier. A stay at one of the city’s first skyscrapers will take you back in time.

Playing host to a highly anticipated new restaurant from a world-renowned chef, a basement speakeasy and a rooftop bar, this recently opened hotspot in the Fulton Market district is a classic in the making. Rooms come in three sizes – snug, cosy and roomy – and feature modern art, custom-designed bed linens, free calls to anywhere in the world and curated guides to the neighborhood. It’s the third US outpost from a celebrated London-based hospitality brand, so you know it has high standards to live up to.

There’s just something about this stylish hotel in the Loop that feels akin to a sleek condo residence in the city. With one entrance on State Street and the other facing the river on Wacker, you can choose your own adventure when heading out. The rooms are sophisticated, and the indoor/outdoor rooftop lounge is a solid way to spend sunset before watching a show in the nearby Theater District.

Contemporary and clean, the Loews is surrounded by greenery and feels like a modern oasis. Its Streeterville location makes the 52-floor hotel ideal for both business and pleasure. Peer out at the Navy Pier Ferris Wheel or take a quick walk to Ohio Street Beach. With design influenced by Chicago architects Mies van der Rohe and Louis Sullivan, intricately clean lines are apparent in every detail of the tower.

Cubs fans, look no further: Hotel Zachary is your spot. Wake up in a handsomely designed suite adorned with vintage photographs and rare Wrigley Field memorabilia directly across from the stadium. Surrounded by both modern and classic sports bars, the hotel is part of the historic stadium’s brand-new renovation. Game day or not, bouncing from pub to pub in Wrigleyville is the perfect way to spend a weekend.