A vast wheat field under a cloudy sky.

Luxury Hotels & Resorts in Countryside from NZ$191

  • 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
8 Oct - 9 Oct
Tomorrow
9 Oct - 10 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Countryside luxury hotels

A multi-story hotel with a prominent "WESTIN" sign on the top.
A spacious lobby with a central seating area, large wooden columns, and potted plants.
A modern hotel room with a large bed, a desk, a chair, and a TV.
A terrace with round tables and chairs, a view of a lake, and a building with a white facade.

1. 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$260
includes taxes & fees
18 Oct - 19 Oct
The Westin Chicago Lombard
An outdoor patio area with tables and chairs, umbrellas, and a fire pit.
A restaurant with yellow chairs, wooden tables, and a bar area in the background.
A modern building with a glass facade and a sign reading "Le MERIDIEN".
A modern lobby with contemporary furniture, a large abstract mural, and a glass coffee table.

2. Le Méridien Chicago - Oakbrook Center

Le Méridien Chicago - Oakbrook Center
Oak Brook
  • Luxurious escape with spa indulgence and dining excellence awaits at this Oak Brook hotel connected to upscale shopping.
NZ$349
includes taxes & fees
29 Oct - 30 Oct
Le Méridien Chicago - Oakbrook Center
A dining table set for six with a cityscape view through large windows.
A modern hotel room with a large window offering a city skyline view, a round table with four chairs, and a ceiling with recessed lighting.
A modern hotel room with a large bed, a desk, a chair, and a view of the cityscape through large windows.
The exterior of the Swissotel building with its distinctive glass facade and the hotel's name displayed prominently.

3. Swissotel - Chicago

Swissotel - Chicago
Downtown Chicago
NZ$485
includes taxes & fees
31 Oct - 1 Nov
Swissotel - Chicago
A modern kitchen with a marble island, fruit bowls, and a city view.
A modern bar area with a central bar, seating, and a distinctive ceiling design.
A modern hotel room with a city view, a seating area with two sofas and a coffee table, and a dining area with a table and chairs.
A modern lounge area with a central bar, seating arrangements, and a decorative chandelier.

4. Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
Downtown Chicago
NZ$457
includes taxes & fees
31 Oct - 1 Nov
Fairmont Chicago at Millennium Park
A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.
A modern restaurant with high ceilings, wooden flooring, and a central chandelier. Tables are set with wine glasses and red cushions.
A room with a bed, a window with curtains, a small table with a vase of flowers, and a chair.
A modern hotel lobby with leather sofas, a coffee table, and a floor lamp.

5. L7 Chicago by LOTTE

L7 Chicago by LOTTE
Downtown Chicago
NZ$406
includes taxes & fees
2 Nov - 3 Nov
L7 Chicago by LOTTE
A spacious indoor area with a high ceiling, large windows, and a central seating area with sofas and tables.
A modern lounge with a fireplace, comfortable seating, and large windows offering city views.
A rooftop bar with seating areas, large windows, and a city view.
A bar area with a large TV screen, multiple shelves of bottles, and orange bar stools.

6. theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel
Downtown Chicago
  • Luxuriate in city centre Chicago at this full-service spa hotel steps from Michigan Avenue and the Riverwalk.
NZ$476
includes taxes & fees
30 Oct - 31 Oct
theWit Chicago, a Hilton Hotel
The Intercontinental hotel facade with a large American flag and a floral display.
A person lying on a bed with a bottle of champagne, surrounded by food and a magazine.
A bar area with a high bar counter, multiple stools, and a seating area with booths and tables.
A swimming pool area with a glass-bottomed pool, a high ceiling with hanging lights, and a staircase with people sitting on it.

7. InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
  • Elegant city centre sanctuary boasts historic charm, luxury spa treatments, and a stunning indoor pool.
NZ$510
includes taxes & fees
31 Oct - 1 Nov
InterContinental Chicago Magnificent Mile by IHG
A rooftop terrace with outdoor seating, a view of the city skyline, and a river.
A modern hotel room with a desk, a sofa, a coffee machine, a TV, and a unique wall art piece.
A modern living room with a sofa, coffee table, and ottoman, a fireplace, and a large window with a city view.
A modern hotel room with a large bed, a desk, a sofa, and a view of the city.

8. LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
  • Unwind in city centre Chicago's LondonHouse with rejuvenating spa treatments and riverfront luxury.
NZ$540
includes taxes & fees
1 Nov - 2 Nov
LondonHouse Chicago, Curio Collection by Hilton
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 hotel room with two beds, a desk, a chair, a large window with a view, and a modern wall design.
A modern hotel room with a large window offering a view of the sea and a cityscape. There is a seating area with a sofa and a small table.

9. 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$300
includes taxes & fees
1 Nov - 2 Nov
The Wade
A modern lounge with a curved glass wall offering a city view, plush seating, and ambient lighting.
A modern building with large glass windows and a sign reading "Thompson Chicago".
A modern lobby with a large mirror, bookshelves, seating areas, and a reception desk.
A modern interior with wooden shelves, a fireplace, and a round mirror.

10. Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt
Downtown Chicago
  • Lavish city centre retreat offers pillowtop beds, rainfall showers, and two stylish bars in Chicago's heart.
NZ$589
includes taxes & fees
1 Nov - 2 Nov
Thompson Chicago, by Hyatt
View all properties

Top Countryside Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"Easy check in, nice room, only issue is water never changed temp and was always different, somedays its nice and warm, other days its cold, cant adjust at all"
John 5-night trip
Posted less than an hour ago
The Chicago Hotel Collection - Magnificent Mile
Congress Plaza Hotel

Congress Plaza Hotel

8/10 Good
"It was a good place to stay, I went for one night and really liked the location. Rooms were clean and I enjoyed the style of the hotel it’s very well maintained"
Alex 1-night trip
Posted 1 hour ago
Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

8/10 Good
"Great location and staff! I also loved the onsite laundry option and water bottle filler in the gym. The room had an “off” (old? Musty?) smell to it but was otherwise alright."
Angela 3-night trip
Posted 1 hour ago
Freehand Chicago
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

10/10 Excellent
"I had a great experience."
annabelle 1-night trip
Posted 2 hours ago
Hotel Saint Clair- Magnificent Mile
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"Well appointed rooms, kind staff, and very responsive"
Whitney 3-night trip
Posted 6 hours ago
Fairmont Chicago at Millennium Park
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"The hotel is in a nice neighborhood and the room was clean. The bed and toilet were both very low to the ground, and there were very few electrical outlets, but otherwise it was a pleasant stay."
peter 1-night trip
Posted 17 hours ago
The Chicago Hotel Collection Ambassador Gold Coast
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Staff was amazing!! They were all so kind and attentive! I enjoyed my stay so much and I’m looking on planning another trip just to stay at this hotel!"
Itzel 3-night trip
Posted 20 hours ago
The Royal Sonesta Chicago Downtown
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent
"CQ is a reliable brand as this property demonstrated. I was particularly pleased with the size of the room and fitness facility. Best CQ I have stayed at and would return. Two quibbles: No desk lamp, therefore a dark work area and no hand soap (use body gel? I bring my own). Housekeeping excellent."
Marcel 2-night trip
Posted 21 hours ago
Club Quarters Hotel, Central Loop, Chicago

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.

Explore a world of travel with Expedia