A vast wheat field under a cloudy sky.

Luxury Hotels & Resorts in Countryside from NZ$190

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Countryside Luxury Hotels

Tonight
26 Sept - 27 Sept
Tomorrow
27 Sept - 28 Sept
Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct

Our top choices for Countryside luxury hotels

An indoor swimming pool with lounge chairs and a stone wall.
A gym with treadmills, elliptical machines, and a view of an outdoor swimming pool.
A modern living room with a large chandelier, leather sofas, and a round coffee table.
A hotel lobby with a reception desk, seating area, and a sign reading "SIP & SAVOR COCKTAILS & EATS".

1. Crowne Plaza Chicago SW - Burr Ridge by IHG

Crowne Plaza Chicago SW - Burr Ridge by IHG
Burr Ridge
NZ$237
includes taxes & fees
26 Oct - 27 Oct
Crowne Plaza Chicago SW - Burr Ridge by IHG
A large hotel with a central courtyard, a lake, and a bridge.
A chef serving food to a couple in a modern dining area with a glass partition and a glass of beer on the table.
A golf course with a swimming pool, lounge area, and a pond.
A spacious, modern interior with large windows offering views of a golf course and a lake.

2. Hilton Chicago/Oak Brook Hills Resort & Conference Center

Hilton Chicago/Oak Brook Hills Resort & Conference Center
Oak Brook
NZ$301
includes taxes & fees
5 Oct - 6 Oct
Hilton Chicago/Oak Brook Hills Resort & Conference Center
A multi-story hotel with a prominent "WESTIN" sign on the top.
A terrace with round tables and chairs, a view of a lake, and a building with a white facade.
A modern hotel room with a large bed, a desk, a chair, and a TV.
A spacious lobby with a central seating area, large wooden columns, and potted plants.

3. The Westin Chicago Lombard

The Westin Chicago Lombard
Lombard
  • Luxury pillow-top beds, refined dining, and pool relaxation define this 4-star Chicago hotel near premier shopping.
NZ$257
includes taxes & fees
11 Oct - 12 Oct
The Westin Chicago Lombard
A modern hotel lobby with a seating area, a bar, and a kitchen.
An outdoor patio area with seating, tables, and string lights.
A DoubleTree by Hilton hotel with a modern design, a covered entrance, and well-maintained landscaping.
A modern living room with a fireplace, a flat-screen TV, a pool table, and a chess table.

4. DoubleTree by Hilton Chicago Midway Airport

DoubleTree by Hilton Chicago Midway Airport
Bedford Park
NZ$472
includes taxes & fees
14 Oct - 15 Oct
DoubleTree by Hilton Chicago Midway Airport
A spacious lobby with a central seating area, a reception desk, and a modern chandelier.
An outdoor dining area with brick walls, string lights, and tables set for guests.
A restaurant with a bar area, multiple dining tables, and chairs.
A hotel lobby with seating areas, a patterned carpet, and a large mirror.

5. DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip
Alsip
NZ$253
includes taxes & fees
25 Oct - 26 Oct
DoubleTree by Hilton Chicago - Alsip
A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.
A modern bar area with high stools, a bar counter, and shelves of liquor bottles.
A modern hotel lobby with a marble floor, seating areas, and a ceiling with a sky-like projection.
A rooftop terrace with a view of a beach and a Ferris wheel, featuring lounge chairs and a colorful mural.

6. The Wade

The Wade
Downtown Chicago
  • Luxurious lakeside retreat in city centre Chicago offers pillowtop beds, designer toiletries, and stunning views near Michigan Avenue.
NZ$313
includes taxes & fees
25 Oct - 26 Oct
The Wade
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.
A spacious outdoor dining area with large windows overlooking the sea, featuring multiple tables and stools.
A view from a room with a large window overlooking a cityscape at night, featuring a river and illuminated buildings.
A modern living room with a large window overlooking a body of water, a tripod, and a sofa.

7. Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
NZ$728
includes taxes & fees
23 Oct - 24 Oct
Sable at Navy Pier Chicago, Curio Collection by Hilton
A modern building with the name 'SENIORAL' prominently displayed on the facade.
A modern kitchen with a built-in microwave, stove, and dishwasher, large windows with city views, and a dining area with a table and chairs.
A balcony with a glass railing, a table, and four chairs.
A bar area with stools, a counter with bottles, and a wall with a leafy design.

8. Sentral Michigan Avenue

Sentral Michigan Avenue
Downtown Chicago
NZ$385
includes taxes & fees
27 Sept - 28 Sept
Sentral Michigan Avenue
A spacious lobby with a central coffee table, sofas, and a large mirror.
A spacious lounge area with leather sofas, round tables, and comfortable chairs, featuring a wooden ceiling and elegant decor.
A spacious lobby with a grand fireplace, elegant columns, and a seating area with chairs and a table.
A balcony with a table set for a meal, featuring a charcuterie board and two glasses of wine, overlooking a cityscape.

9. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
NZ$357
includes taxes & fees
27 Sept - 28 Sept
The Chicago Hotel Collection Ambassador Gold Coast
A dining table set for six with a cityscape view through large windows.
A modern hotel room with a large bed, a desk, a chair, and a view of the cityscape through large windows.
A modern hotel room with a large window offering a cityscape view, a green sofa, two armchairs, and a coffee table with flowers.
The exterior of the Swissotel building with its distinctive glass facade and the hotel's name displayed prominently.

10. Swissotel - Chicago

Swissotel - Chicago
Downtown Chicago
NZ$542
includes taxes & fees
27 Sept - 28 Sept
Swissotel - Chicago
View all properties

Top Countryside Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"Clean room and easy check in"
Carly 1-night trip
Posted less than an hour ago
The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"Great location, clean room, would stay there again!!"
Amber 1-night trip
Posted 2 hours ago
The Chicago Hotel Collection - Magnificent Mile
The Wade

The Wade

8/10 Good
"The only issues I had was that the shower gel pump wasn’t working and the tv would blink on and off on certain channels."
Ayanna 3-night trip
Posted 8 hours ago
The Wade
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

10/10 Excellent
"The staff was really nice. The room was very clean and they also respond promptly to your request."
Shaniece Marie 2-night trip
Posted 13 hours ago
Hotel Saint Clair- Magnificent Mile
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

8/10 Good
"Unfortunately our room had wet carpets so we had to change rooms. We would have preferred the original king instead of two doubles. Manager was helpful . Housekeeping was a bit lax, forgetting towels and replacement coffee mugs. Valet staff was friendly and helpful, It was a nice stay but not stellar."
Pia 3-night trip
Posted 14 hours ago
Fairmont Chicago at Millennium Park
Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Cool"
Carlos Joel 2-night trip
Posted 18 hours ago
Congress Plaza 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 Soldier Field, Navy Pier and Wrigley Field. If you have some spare time during your trip, you might want to check out United Center and Michigan Avenue.