Luxury Hotels & Resorts in Countryside from NZ$209

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Check availability on Countryside Luxury Hotels

Next weekend
5 Jun - 7 Jun
In two weeks
12 Jun - 14 Jun

Our top choices for Countryside luxury hotels

Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,512 reviews)
The price is NZ$517
includes taxes & fees
30 June - 1 July
Sable at Navy Pier Chicago, Curio Collection by Hilton
Couples treatment room(s), sauna, body treatments, aromatherapy

Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel
4.0 star property
East Hazel Crest
9.4 out of 10, Exceptional, (401 reviews)
The price is NZ$300
includes taxes & fees
4 June - 5 June
Wind Creek Southland Casino and Hotel
View from property

The Blackstone, Autograph Collection

The Blackstone, Autograph Collection
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,002 reviews)
The price is NZ$342
includes taxes & fees
30 June - 1 July
The Blackstone, Autograph Collection
Lobby

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (1,520 reviews)
The price is NZ$310
includes taxes & fees
22 June - 23 June
The Chicago Hotel Collection Ambassador Gold Coast
2 restaurants, breakfast served

The Drake

The Drake
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,473 reviews)
The price is NZ$342
includes taxes & fees
29 June - 30 June
The Drake
Reception hall

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,593 reviews)
The price is NZ$445
includes taxes & fees
29 June - 30 June
Eurostars Magnificent Mile
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,178 reviews)
The price is NZ$472
includes taxes & fees
29 June - 30 June
Sentral Michigan Avenue
Lobby

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,245 reviews)
The price is NZ$368
includes taxes & fees
28 June - 29 June
Silversmith Hotel Chicago Downtown
Interior detail

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,077 reviews)
The price is NZ$482
includes taxes & fees
29 June - 30 June
Staypineapple, An Iconic Hotel, The Loop
Room service – dining

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1,852 reviews)
  • cleanliness
    Luxurious lakeside retreat in city centre Chicago offers pillowtop beds, designer toiletries, and stunning views near Michigan Avenue.
The price is NZ$574
includes taxes & fees
29 June - 30 June
The Wade
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top Countryside Hotel Reviews

River Hotel

River Hotel

8/10 Good
"Simple, but quite adequate hotel in ideal location. I love the self check-in/out option, microwave, and refrigerator."
Susan 1-night trip
Posted 1 hour ago
River Hotel

Frequently asked questions

Are you searching for a great accommodation for your luxury trip to Countryside?
Use Expedia to arrange your flight to Chicago Midway Airport (MDW) airport or Chicago O'Hare International Airport (ORD) airport, and then select from a variety of places to stay that will deliver the luxury you want. Amenities are important when you plan a trip, so we make it easy to find what you need to make your stay special. If you want an upscale hotel with a spa, an indoor pool or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Countryside has to offer. During your visit, you might want to enjoy the restaurants which Countryside is known for.
When can I expect good weather in Countryside?
Planning for the weather is an important factor for making your trip to Countryside a success, especially when you're splurging. The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of -1°C. Average annual precipitation for Countryside is 1236 mm.
What's there to see and do in Countryside?
Enjoy Countryside and visit Navy Pier, Wrigley Field and United Center. If you have some spare time during your trip, you might want to check out Soldier Field and Michigan Avenue.