The Best Five-Star Hotels in Chicago, Illinois

Skyscrapers dominate Chicago’s skyline
Skyscrapers dominate Chicago’s skyline | © Michael Paskvan / Alamy Stock Photo
Photo of Jacquelyn Lumley
6 August 2020

The Windy City is home to many five-star hotels that promise indulgent luxury, glamorous design and quality service.

Chicago is all about modern urban living, but its historical buildings were some of the first skyscrapers in the country. Staying somewhere within easy walking distance of the city’s turn-of-the-century architecture is key, and each hotel on this list stands out for its location alone. High hospitality standards, top-notch amenities, mind-blowing views and exclusive experiences are the cherries on top.

LondonHouse, New Eastside

Suite Hotel, Luxury
4.6/5 (2629 Reviews)
Courtesy of LondonHouse Chicago / Expedia

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.

More info

The Langham, River North

Suite Hotel, Luxury
4.9/5 (1054 Reviews)
Courtesy of the Langham / Expedia
The Chicago River is experiencing a bit of a renaissance, and The Langham is perched just above the action. Top critics continually rank this five-star property among the best in the country. Treat yourself to a massage at the award-winning Chuan Spa before cruising to dinner on a water taxi, then dozing off in a room that faces either the lake or the river – you decide.
More info

The Hoxton, Fulton Market

4.5/5 (326 Reviews)
Courtesy of The Hoxton / Expedia

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.

More info

Renaissance Chicago Downtown Hotel

Suite Hotel
4.5/5 (940 Reviews)
Courtesy of Renaissance Chicago Downtown Hotel / Expedia

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.

More info

Waldorf Astoria Chicago, Rush and Division

Suite Hotel, Luxury
4.7/5 (979 Reviews)
Courtesy of Waldorf Astoria Chicago / Expedia
Treat yourself to a luxurious stay at the Waldorf Astoria. The entrance terrace, dressed with string lights and violet awnings, looks like something straight out of a storybook. The hotel is located in a prime spot in the exclusive Gold Coast neighborhood, steps from the Magnificent Mile. Relax and take in views of the city before enjoying a happy-hour martini and a swanky Italian dinner on nearby Rush Street.
More info

Loews Chicago Hotel, Streeterville

Suite Hotel
4.7/5 (1301 Reviews)
Courtesy of Loews Chicago Hotel / Expedia

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.

More info

Why Book With Culture Trip?

  • Free cancellation

    In these uncertain times, cancel or change for free on select properties.

  • Price-match guarantee

    Find a better price on your booking and we’ll match it. Simple.

  • Unbiased & trustworthy

    Book from recommendations handpicked by travel experts.

  • Hotel Zachary, Wrigleyville

    Independent Hotel
    4.7/5 (578 Reviews)
    Courtesy of Hotel Zachary / Expedia

    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.

    More info

    Four Seasons Hotel Chicago, Streeterville

    4.7/5 (838 Reviews)
    Courtesy of Four Seasons Hotel Chicago / Expedia
    The Four Seasons Hotel Chicago rises from a shopping mall in the heart of the historic Gold Coast district. Enter through a glossy marble lobby, relax in rooms with views of crushed-opal colored Lake Michigan and swim under the domed skylights of the Roman-style pool. The Author Suite encourages you to lose yourself in the pages of the hotel’s private literary collection – featuring personalised editions from the likes of horror wordsmith Stephen King and gothic fiction author Anne Rice – while evenings are best spent sipping one of prohibition-era libations served up in the lobby bar.
    More info

    The Ritz-Carlton Chicago, Streeterville

    Chain Hotel, Spa Hotel, Luxury
    4.6/5 (989 Reviews)
    Courtesy of The Ritz-Carlton Chicago / Expedia
    The Ritz-Carlton Chicago is as elegant as you would expect. The apartment-style rooms are dressed in natural blue and grey tones with golden accents, with ornamental driftwood and bespoke furnishings. Each includes a marble bathroom with a deep-soaking tub and Asprey toiletries alongside a sleek, fully-equipped kitchen. Once you’ve taken in the far-reaching views of Lake Michigan, head down to the spa for a spine-tingling hot river stone massage. In the morning, pull up a seat at the atrium-style cafe for fresh-pressed juices and spend evenings at the hotel’s steakhouse Torali, tearing into tender dry-aged meats.
    More info

    Sofitel Chicago Magnificent Mile, Near North Side

    4.6/5 (1689 Reviews)
    Courtesy of Sofitel Chicago Magnificent Mile / Expedia
    Inspired by the French-coined art de vivre (art of living), Sofitel Chicago offers luxury with a playful twist. The hotel is steps away from the Magnificent Mile and its parade of deluxe stores, so you can spend the day shopping before unwinding in modern rooms with beechwood walls, Bose bluetooth speakers and 55-inch TVs. Meet friends on the teddy-bear-reminiscent sofas of the lobby (made up of honey-colored velvet with tartan cushions) and pull up a lime-green stool in Le Bar for Moscow Mule cocktails and macarons.
    More info

    Conrad Chicago, River North

    Chain Hotel, Luxury
    4.7/5 (756 Reviews)
    Courtesy of Conrad Chicago / Expedia
    The Conrad Chicago envelops you in its warm palette of fiery-orange velvets, tobacco leathers and bronze-toned carpets. The cosy theme extends to the Baptiste & Bottle bar, which serves throat-burning, barrel-aged bourbon and classic cocktails like the dark rum-infused Old Cuban. The mid-century-modern rooms are decorated with abstract art and treat you to eye-popping city views and Nespresso coffee machines. Only open in the warmer seasons, rooftop restaurant Noyane is a sun-soaked excuse to cool off with Spiked Snowballs – a shaved ice delicacy drenched in booze such as dragon fruit strawberry rum.
    More info

    Chloe Byrne contributed additional reporting to this article.

    These recommendations were updated on August 6, 2020 to keep your travel plans fresh.

    Cookies Policy

    We and our partners use cookies to better understand your needs, improve performance and provide you with personalised content and advertisements. To allow us to provide a better and more tailored experience please click "OK"