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Check availability on Countryside Luxury Hotels

This weekend
5 Jun - 7 Jun
Next weekend
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, (2,521 reviews)
The price is AED 846
AED 1,133 total
includes taxes & fees
30 Jun - 1 Jul
Sable at Navy Pier Chicago, Curio Collection by Hilton
Couples treatment rooms, 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, (406 reviews)
The price is AED 486
AED 544 total
includes taxes & fees
15 Jun - 16 Jun
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, (1,004 reviews)
The price is AED 513
AED 718 total
includes taxes & fees
1 Jul - 2 Jul
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, (1,532 reviews)
The price is AED 574
AED 683 total
includes taxes & fees
28 Jun - 29 Jun
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, (1,474 reviews)
The price is AED 639
AED 759 total
includes taxes & fees
28 Jun - 29 Jun
The Drake
Reception hall

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,607 reviews)
The price is AED 735
AED 873 total
includes taxes & fees
1 Jul - 2 Jul
Eurostars Magnificent Mile
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,179 reviews)
The price is AED 809
AED 1,057 total
includes taxes & fees
29 Jun - 30 Jun
Sentral Michigan Avenue
Lobby

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,255 reviews)
The price is AED 522
AED 733 total
includes taxes & fees
28 Jun - 29 Jun
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, (1,082 reviews)
The price is AED 511
AED 716 total
includes taxes & fees
1 Jul - 2 Jul
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, (1,856 reviews)
  • cleanliness
    Luxurious lakeside retreat in downtown Chicago offers pillowtop beds, designer toiletries, and stunning views near Michigan Avenue.
The price is AED 1,154
AED 1,372 total
includes taxes & fees
28 Jun - 29 Jun
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

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

2/10 Terrible
"They cancelled my reservation without notifying Expedia or me and I had to find a new place to stay. They are the worst hotel ever. Do not stay here. Do not trust them. They even admitted that the reason they did it is because my rate that I booked at was too low."
Jenna 2-night trip
Posted 7 hours ago
The Chicago Hotel Collection - Magnificent Mile

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Frequently asked questions

Are you searching for a great accommodation for your luxury holiday in Countryside?
Use Expedia to arrange your flight to Chicago Midway Airport (MDW) airport or Chicago O'Hare Intl. 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 temp of 71°F, while the coldest months are January and February with an average of 31°F. Average annual precipitation for Countryside is 49 inches.
What's there to see and do in Countryside?
Enjoy Countryside and visit Soldier Field, Michigan Avenue, and Navy Pier. If you have some spare time during your trip, you might want to check out Wrigley Field and United Center.