Looking for Chicago hotels worth the stay? These are my tried-and-tested favorites.
These are hotels I’ve actually stayed at and loved, the ones I’d send my friends to. When you comment HOTEL on my posts, this is where you land. Book through my links and I may earn a commission at no extra cost to you, which helps me keep sharing honest recommendations.
Chicago Hotels Worth the Stay: Hotel Riu Plaza Chicago
The rooftop here is the whole reason to come. You’re right on the Magnificent Mile with the city spread out below you, and it feels like an escape without leaving downtown. If you want a Chicago staycation that feels like a getaway, this is it.
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Chicago Hotels Worth the Stay: Loews Chicago Hotel
This one is all about the room. Big windows, a deep soaking tub, and skyline views that make you want to stay in. It’s my pick when I want a quiet, comfortable night in the city.
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Chicago Hotels Worth the Stay: Waldorf Astoria Chicago
I came for the spa and stayed for the whole experience. It’s old-school luxury in the Gold Coast, the kind of place where everything feels considered. Worth it for a special occasion or a reset day.
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LondonHouse Chicago
The rooftop views of the river and lake are unreal, and the location at Michigan and Wacker puts you in the middle of everything. It’s a classic Chicago stay that never disappoints.
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theWit Chicago (ROOF on theWit)
ROOF is one of my favorite rooftops in the city, and staying at theWit means you’re already there. Sleek rooms, great energy, right in the Loop. Perfect for a night out downtown.
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Radisson Blu Aqua Hotel Chicago
That wavy glass building in Lakeshore East is hard to miss, and the rooms live up to the architecture. Great pick if you want modern style close to Millennium Park and the lake.
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Chicago Hotels Worth the Stay: Sable at Navy Pier Chicago
You can’t beat waking up on the lake. Sable sits right at Navy Pier with some of the best water views in the city. It’s a fun one for a weekend escape without leaving Chicago.
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Blue Harbor Resort, Sheboygan WI
A lakeside resort on Lake Michigan with a waterpark the kids will love. It’s an easy drive from Chicago and feels like a real vacation. Great for a family weekend.
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Renaissance Milwaukee West Hotel, Wauwatosa WI
Sleek and modern in Wauwatosa, just outside Milwaukee. The restaurant scene here is a standout. Easy stop if you’re heading up to Wisconsin.
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Grand Geneva Resort & Spa, Lake Geneva WI
A full resort in Lake Geneva with skiing in winter, golf in summer, and a spa year-round. It’s the Midwest getaway that has a little bit of everything.
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Amway Grand Plaza Hotel, Grand Rapids MI
A grand historic hotel in downtown Grand Rapids. Beautiful old-world details with everything you need. Worth the drive for a Michigan weekend.
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I Hotel and Conference Center, Champaign IL
My pick when I’m down in Champaign. Comfortable, quiet, and close to campus. Easy and reliable.
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Embassy Suites Rockford Riverfront, Rockford IL
Right on the river in downtown Rockford with spacious suites. A solid home base for exploring the city.
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Coming to Chicago? My 3-day Chicago travel guide has my full local itinerary — where to stay, what to eat, and what to do. Get it here
For more Chicago trip ideas, check out my favorite Chicago skyline views and my 3-day Chicago itinerary.
