Planning a stay in the Windy City? From luxury skyscraper stays to charming boutique hotels, here are the top 10 hotels in Chicago — each with pros, cons, and embedded affiliate booking links.
1. The Langham, Chicago
Why stay here: Sophisticated riverside hotel with world-class service and amenities.
Pros:
- Spacious rooms with city or river views
- Award-winning spa and wellness center
- Close to the Magnificent Mile
Cons:
- Premium pricing
- Valet parking only
- Often busy during peak seasons
2. LondonHouse Chicago
Why stay here: Stylish hotel in a historic building with a rooftop bar overlooking the river.
Pros:
- Incredible rooftop views
- Modern rooms with tech amenities
- Near Millennium Park and Riverwalk
Cons:
- Some rooms lack natural light
- Rooftop can get crowded
- Extra fees for early check-in
3. Pendry Chicago
Why stay here: Art Deco luxury in the Carbide & Carbon Building with a sleek modern twist.
Pros:
- Gorgeous architecture
- Excellent on-site dining
- Steps from Michigan Avenue
Cons:
- Rooms on the smaller side
- Noise from nearby nightlife
- High daily destination fees
4. The Peninsula Chicago
Why stay here: Refined 5-star property offering exceptional hospitality and luxury.
Pros:
- Heated indoor pool and rooftop spa
- Highly personalized service
- Spacious marble bathrooms
Cons:
- One of the priciest in the city
- Valet-only parking
- Dining options are upscale only
5. Hotel Zachary
Why stay here: Boutique hotel located next to Wrigley Field, ideal for Cubs fans.
Pros:
- Baseball-themed design
- Vibrant neighborhood feel
- Great dining nearby
Cons:
- Not central to downtown
- Can be noisy on game days
- Smaller lobby area
6. The Robey
Why stay here: Trendy boutique hotel in Wicker Park with stunning skyline views.
Pros:
- Rooftop lounge with cityscape views
- Hip, walkable neighborhood
- Retro-chic decor
Cons:
- Far from downtown attractions
- No on-site parking
- Minimalist room design not for all
7. Palmer House Hilton
Why stay here: Historic hotel with timeless elegance and central Loop location.
Pros:
- Grand lobby and classic architecture
- Indoor pool and spa
- Easy access to theaters and museums
Cons:
- Rooms may feel dated
- Long elevator wait times
- Extra fees for Wi-Fi and amenities
8. Viceroy Chicago
Why stay here: Contemporary Gold Coast hotel with a rooftop pool and luxury design.
Pros:
- Sleek, modern rooms
- Rooftop bar and pool
- Quiet, upscale neighborhood
Cons:
- Rooftop can be seasonal
- Parking is expensive
- Few budget dining spots nearby
9. Freehand Chicago
Why stay here: Stylish and affordable hostel-hotel hybrid in River North.
Pros:
- Budget-friendly
- Hip bar and lounge
- Close to public transit
Cons:
- Shared bathrooms in some rooms
- Small rooms
- Can be noisy at night
10. AC Hotel by Marriott Chicago Downtown
Why stay here: Practical option near Michigan Avenue for business and shopping.
Pros:
- Free breakfast
- Spacious rooms
- Good value for location
Cons:
- No full restaurant
- Basic decor
- Can get crowded with groups
Leave a comment