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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 AED 849
AED 1,136 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, (401 reviews)
The price is AED 590
AED 661 total
includes taxes & fees
3 Jun - 4 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, (1,002 reviews)
The price is AED 541
AED 752 total
includes taxes & fees
30 Jun - 1 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, (1,520 reviews)
The price is AED 574
AED 683 total
includes taxes & fees
22 Jun - 23 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, (1,473 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, (3,593 reviews)
The price is AED 823
AED 978 total
includes taxes & fees
29 Jun - 30 Jun
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 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, (2,245 reviews)
The price is AED 587
AED 810 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, (1,077 reviews)
The price is AED 790
AED 1,048 total
includes taxes & fees
29 Jun - 30 Jun
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 downtown Chicago offers pillowtop beds, designer toiletries, and stunning views near Michigan Avenue.
The price is AED 1,062
AED 1,262 total
includes taxes & fees
29 Jun - 30 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 Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"A very quick trip to Chicago and this hotel was perfect! Close to the metro, so there was no need for a car or an uber. Everything is either in walking distance or on the metro line…perfect location! The hotel itself is beautiful and the people there are lovely. We had the option to pay $25 for an early checkin which was very helpful. The room was clean with an incredible view of the river. We would absolutely stay here again!"
Ananda 2-night trip
Posted 1 hour ago
The Royal Sonesta Chicago Downtown

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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 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.