A vast wheat field under a cloudy sky.

Luxury Hotels & Resorts in Countryside from NZ$185

  • 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
2 Oct - 3 Oct
Tomorrow
3 Oct - 4 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Countryside luxury hotels

A multi-story hotel with a prominent "WESTIN" sign on the top.
A long corridor with a patterned carpet, large windows, and a bench on the left.
A spacious lobby with a central seating area, large wooden columns, and potted plants.
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$259
includes taxes & fees
11 Oct - 12 Oct
The Westin Chicago Lombard
An outdoor patio area with tables and chairs, umbrellas, and a fire pit.
A modern building with a glass facade and a sign reading "Le MERIDIEN".
A modern hotel room with a large bed, a flat-screen TV, a dining table, a sofa, and a coffee table.
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$348
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 cityscape view, a green sofa, two armchairs, and a coffee table with flowers.
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.

3. Swissotel - Chicago

Swissotel - Chicago
Downtown Chicago
NZ$466
includes taxes & fees
31 Oct - 1 Nov
Swissotel - Chicago
A rooftop terrace with outdoor seating, a view of the city skyline, and a river.
A modern room with a view of a river and high-rise buildings.
A modern hotel room with a desk, a sofa, a coffee machine, a TV, and a unique wall art piece.
A modern hotel room with a large bed, a desk, a sofa, and a view of the city.

4. 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$553
includes taxes & fees
1 Nov - 2 Nov
LondonHouse Chicago, Curio Collection by Hilton
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 bar area with a large TV screen, multiple shelves of bottles, and orange bar stools.
A rooftop bar with seating areas, large windows, and a city view.

5. 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$527
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 sitting by a window with a cityscape view.
A bar area with a high bar counter, multiple stools, and a seating area with booths and tables.
A person lying on a bed with a bottle of champagne, surrounded by food and a magazine.

6. 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$533
includes taxes & fees
31 Oct - 1 Nov
InterContinental Chicago Magnificent Mile by IHG
A person relaxing on a sofa with a laptop, a glass of red wine, and a small table with a vase of flowers and a telephone.
A bar area with a long counter, multiple shelves of bottles, and four bar stools.
A modern restaurant with high ceilings, wooden flooring, and a central chandelier. Tables are set with wine glasses and red cushions.
A modern hotel lobby with leather sofas, a coffee table, and a floor lamp.

7. L7 Chicago by LOTTE

L7 Chicago by LOTTE
Downtown Chicago
NZ$409
includes taxes & fees
2 Nov - 3 Nov
L7 Chicago by LOTTE
A restaurant with tables and chairs arranged under a large open space with a view of the sea.
Exterior
A spacious hall with high ceilings, large wooden pillars, and a view of the sea through expansive windows.
Sports facility

8. Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
  • Historic Chicago landmark with designer rooms and rooftop terrace invites guests into elegant luxury steps from Millennium Park.
NZ$598
includes taxes & fees
31 Oct - 1 Nov
Chicago Athletic Association, a Hyatt Hotel
A rooftop lounge with outdoor seating and a city skyline view.
The exterior of the Carbide and Carbon Building with large windows and a balcony area.
A spacious living area with a green sofa, a coffee table, and a bookshelf filled with plants and decorative items.
An indoor cafe with tables and chairs, large windows, and a view of the cityscape.

9. Pendry Chicago

Pendry Chicago
Downtown Chicago
  • Indulge in architectural splendour and upscale amenities at this Art Deco Chicago hotel, where luxury meets city centre convenience.
NZ$742
includes taxes & fees
31 Oct - 1 Nov
Pendry Chicago
A modern reception area with a marble reception desk, a sofa, armchairs, and a coffee table.
A couple in white robes sitting in a bathtub with candles and a bottle of champagne.
A historic building with large windows and a marquee sign for a hotel.
A grand hotel lobby with a high ceiling, a large chandelier, and a staircase leading to an upper floor.

10. JW Marriott Chicago

JW Marriott Chicago
Downtown Chicago
  • Spa indulgence awaits in city centre Chicago where luxurious treatments and premium dining create memorable moments.
NZ$600
includes taxes & fees
30 Oct - 31 Oct
JW Marriott Chicago
View all properties

Top Countryside Hotel Reviews

L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"Stayed 1 night at the L7 and totally wish we had stayed there the other 4 nights of our vacation. The room was clea and very well appointed. Lots of outlets and plugs for charging. My husband got delicious coffee at the bar in the morning. We didn’t eat any meals there as we were leaving early the next morning. Staff was friendly and helpful. Will definitely stay here again the next time we come to Chicago."
Eileen 1-night trip
Posted less than an hour ago
L7 Chicago by LOTTE
Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"The check-in process went smoothly, the location is great, and the rooms are spacious. Most of the amenities do show their age, but overall, it is an excellent place to stay for the price."
Muhammad Salman 1-night trip
Posted less than an hour ago
Congress Plaza Hotel
River Hotel

River Hotel

10/10 Excellent
"Clean the carpets"
Malinda 2-night trip
Posted 1 hour ago
River Hotel
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

10/10 Excellent
"The staff was extremely friendly"
Russell 2-night trip
Posted 1 hour ago
Hampton Inn Chicago Downtown/Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

10/10 Excellent
"Magnificent property. Truly breathtaking! My wife and I will be returning for certain!"
Adam 1-night trip
Posted 1 hour ago
Hyatt Regency O'Hare Chicago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent
"It was definitely an awesome experience and setting."
Andrea 2-night trip
Posted 7 hours ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

8/10 Good
"Older hotel. Everything seemed tight (room, hallways, elevator. Sometimes it takes a while for valet since the drivers had to manage two hotels, averaging around 10-15min. The staff were very friendly though. Would I stay here again? Probably not."
Choua 2-night trip
Posted 14 hours ago
Hotel Saint Clair- Magnificent Mile
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Hotel was very clean, grateful housekeeping came in everyday and provided clean towels. Room view was very nice and as advertised."
Erica 4-night trip
Posted 2 days ago
The Royal Sonesta Chicago Downtown
Central Loop Hotel

Central Loop Hotel

10/10 Excellent
"I liked the location and staff"
Murray 1-night trip
Posted 2 days ago
Central Loop 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.

Explore a world of travel with Expedia