Chicago Holiday Rentals, Illinois: Private House Rentals

A river with a yellow boat, surrounded by tall buildings and a bridge.

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Our top choices for Chicago hotels

1. Hotel Riu Plaza Chicago

Downtown Chicago

Cicely

4.925.537 ₫

6.599.109 ₫ total

includes taxes & fees

31 Aug - 1 Sept

Room, 2 Queen Beds, Lake View | Premium bedding, pillow-top beds, in-room safe, desk

2. Hyatt Regency Chicago

Downtown Chicago

Emily

5.736.500 ₫

7.750.218 ₫ total

includes taxes & fees

7 Sept - 8 Sept

2 restaurants; breakfast, lunch, dinner and brunch served

3. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Farhan

6.623.050 ₫

8.786.769 ₫ total

includes taxes & fees

23 Aug - 24 Aug

2 restaurants; breakfast, lunch and dinner served

2 bars/lounges, rooftop bar, cocktail bar

4. LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Luis

5.141.990 ₫

6.878.612 ₫ total

includes taxes & fees

30 Aug - 31 Aug

55-inch LCD TV with cable channels, TV, pay films

Breakfast, lunch, dinner and brunch served

5. L7 Chicago by LOTTE

Downtown Chicago

Kelly

5.047.860 ₫

6.001.400 ₫ total

includes taxes & fees

30 Aug - 31 Aug

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

6. Eurostars Magnificent Mile

Downtown Chicago

Kristine

5.215.000 ₫

6.200.114 ₫ total

includes taxes & fees

23 Aug - 24 Aug

7. Hyatt Place Chicago/River North

Downtown Chicago

Shoma

4.432.750 ₫

5.270.097 ₫ total

includes taxes & fees

23 Aug - 24 Aug

8. Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Brian

4.188.949 ₫

4.980.239 ₫ total

includes taxes & fees

30 Aug - 31 Aug

Hypo-allergenic bedding, in-room safe, desk, laptop workspace

9. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Evelyn

4.499.241 ₫

5.349.461 ₫ total

includes taxes & fees

30 Aug - 31 Aug

10. The Royal Sonesta Chicago Downtown

Downtown Chicago

Sandra

5.058.550 ₫

6.848.511 ₫ total

includes taxes & fees

1 Sept - 2 Sept

11. Congress Plaza Hotel

Downtown Chicago

Christina

2.992.106 ₫

3.557.315 ₫ total

includes taxes & fees

8 Sept - 9 Sept

Premium Room, 1 King Bed (View) | Premium bedding, pillow-top beds, in-room safe, desk

12. citizenM Chicago Downtown

Downtown Chicago

lakadria

4.432.750 ₫

5.270.097 ₫ total

includes taxes & fees

7 Sept - 8 Sept

Daily cooked-to-order breakfast for a fee

13. Sofitel Chicago Magnificent Mile

Downtown Chicago

Jennifer

7.016.783 ₫

9.117.464 ₫ total

includes taxes & fees

30 Aug - 31 Aug

Hypo-allergenic bedding, pillow-top beds, in-room safe, desk

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

Downtown Chicago

Dawn

4.477.078 ₫

6.221.864 ₫ total

includes taxes & fees

7 Sept - 8 Sept

15. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Patrick

5.293.225 ₫

6.293.115 ₫ total

includes taxes & fees

23 Aug - 24 Aug

Room, 2 Queen Beds (Drinks & Snacks) | Premium bedding, in-room safe, soundproofing, free WiFi

16. Hilton Garden Inn Chicago Downtown Riverwalk

Downtown Chicago

Daniel

4.041.104 ₫

4.804.469 ₫ total

includes taxes & fees

30 Aug - 31 Aug

Room, 1 King Bed with Sofa bed, Corner | In-room safe, desk, laptop workspace, soundproofing

17. Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

Kimberly

4.693.500 ₫

5.580.101 ₫ total

includes taxes & fees

7 Sept - 8 Sept

Outdoor pool, pool cabanas (surcharge), pool umbrellas

18. DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

Steffany

4.192.667 ₫

4.985.096 ₫ total

includes taxes & fees

30 Aug - 31 Aug

Premium bedding, in-room safe, free cots/infant beds, free WiFi

19. Aloft by Marriott Chicago Mag Mile

Downtown Chicago

Jasmin

3.911.250 ₫

4.650.088 ₫ total

includes taxes & fees

16 Aug - 17 Aug

Premium bedding, in-room safe, desk, blackout curtains

20. Courtyard by Marriott Chicago Magnificent Mile

Downtown Chicago

Queenie

4.041.625 ₫

4.805.088 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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Holiday Rentals in Chicago

Aparthotel

Classic Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Living area | 49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

Downtown Chicago

"Nice ez stay convenient location"

Aparthotel

Premium Apartment, 2 Bedrooms | Private kitchen | Coffee/tea maker, oven, stovetop, dishwasher

Sentral Michigan Avenue

Downtown Chicago

"The room and building were beautiful and located in a great place."

Aparthotel

Full-sized fridge, microwave, oven, stovetop

Deluxe Room, 1 Single Bed, City View | Living area | Flat-screen TV

Level Chicago – Old Town

Downtown Chicago

"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."

Aparthotel

Studio | Private kitchen | Coffee/tea maker, fridge, oven, toaster

Ground Floor Studios in Chicago by 747 Lofts

West Town

"It’s a really nice place. Its quite a distance from downtown Chicago. But it’s like 3 minutes from Chicago Blue line and a minute away from the bus station. Food is not a problem since there is a Korean grocery nearby. There is also a nearby Catholic church. The ameneties in this loft hotel is complete so if you are looking for a budget style trip and accommodation, I highly recommend this place."

Aparthotel

50-inch Smart TV with satellite channels

The Neighborhood Hotel-Little Italy

Near West Side

"View from room was spectacular - clean and perfect location s"

Aparthotel

Superior Apartment, 2 Bedrooms, City View | Private kitchen | Fridge, microwave, oven, stovetop

Superior Apartment, 3 Bedrooms | Living area

McCormick Suites by Slumber Stay

Near South Side

"Clean room"

Aparthotel

Wrigleyville Suites

Lakeview

"would not recommend"

Aparthotel

Seasonal outdoor pool, open 10:00 AM to 10:00 PM, pool loungers

Kasa River North Chicago

Downtown Chicago

"Great property, fantastic location, lovely views of the city."

Aparthotel

Classic Studio, 1 King Bed, Non Smoking, Kitchen (Self Check-in with Virtual Front Desk) | In-room dining

Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | City view

Kasa South Loop Chicago

Downtown Chicago

"Had to extend my stay, I was able to get excellent help and the transaction was smooth. Recommended, I already booked my next stay."

Aparthotel

2 Bedroom King and Queen | Iron/ironing board, free WiFi, individually decorated

Kasa Lake Shore Chicago

Downtown Chicago

"Great location and super clean!"

Aparthotel

Chicago Second Floor Studio by 747 Lofts

West Town

"i loved this place! would definitely come again"

Aparthotel

River West, Third Floor Chicago by 747 Lofts

West Town

"Loved the space and location "

Aparthotel

Chicago Third Floor Studio by 747 Lofts

West Town

"Clean, easy to check in, all the household items you’d expect"

Aparthotel

River West, Second Floor Chicago by 747 Lofts

West Town

"I need to somewhere to stay for a night in Chicago and found this place. It had a varying level of reviews but found the property more the suitable for what I paid. Easy to follow instructions to get in, clean, and convienent. They even provide ear plugs to drown out the sounds of the city."

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Where to stay in Chicago

Find the best Chicago areas for the activities you enjoy most.

A river with yellow boats, a bridge, and tall buildings.

A nighttime cityscape with illuminated buildings and a bridge over a river.

A nighttime cityscape with illuminated skyscrapers and a river.

A city skyline with modern skyscrapers, a marina with boats, and a park with people walking.

A river with a bridge, modern buildings, and a historic tower.

The Loop

The Loop pulses with energy as Chicago's iconic skyline reaches skyward. Art and business collide at every corner, from Cloud Gate's gleaming curves to historic skyscrapers. Experience world-class culture at the Art Institute or Chicago Symphony Orchestra. Named for the elevated train tracks encircling city centre, this area offers excellent transit connections. Millennium Park provides green space amid urban intensity. Weekdays buzz with business crowds while weekends reveal a quieter side of this architectural wonderland.

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A city street with a train passing overhead, cars, pedestrians, and a red brick building.

A river with boats, tall buildings, and a bridge.

A Trump Building with a glass facade reflecting the cityscape.

A large, historic building with a central tower and multiple windows, located near a body of water.

A nighttime cityscape with illuminated buildings, a river, and a bridge.

River North

River North captivates visitors with America's largest concentration of art galleries outside Manhattan. This upscale Chicago area blends high-end dining with vibrant nightlife along the scenic riverfront. Stunning architecture frames the bustling streets. The area boasts exceptional transit options with three nearby metro stations. Browse through contemporary exhibits, enjoy cocktails at stylish rooftop bars, or shop at luxury boutiques. Merchandise Mart and Bally's Casino offer additional entertainment in this walker-friendly urban playground.

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A historic castle-like building with intricate stonework and a paved walkway.

A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.

A city intersection with tall buildings, including a historic building labeled "Water Tower Place."

A cityscape with tall buildings, a prominent clock tower, and a busy intersection with moving vehicles.

A nighttime cityscape with illuminated skyscrapers and a prominent clock tower.

Magnificent Mile

Chicago's famous Magnificent Mile dazzles with luxury shopping and architectural wonders. Michigan Avenue showcases high-end retailers like Bloomingdale's and Neiman Marcus alongside historic landmarks such as the Water Tower. The district seamlessly blends shopping paradise with cultural attractions. Business travellers appreciate the numerous office buildings and hotels lining North Michigan Avenue. Visitors can enjoy fine dining establishments, explore the Chicago Riverwalk, or venture to nearby attractions like Navy Pier and the Art Institute of Chicago. The area's stunning skyline views and riverfront access create an unforgettable urban experience.

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A cityscape with modern skyscrapers and a curved highway.

A cityscape with a mix of modern and older buildings, including a prominent red building with many windows and balconies.

A cityscape with a mix of modern and older buildings, a busy highway, and a large parking lot.

A city skyline with modern skyscrapers, a parking lot, and a distinctive building with a geometric facade.

A cityscape with a prominent skyscraper, a dense urban area, and a clear sky.

West Loop

West Loop has transformed from industrial roots into Chicago's trendiest food destination. Old warehouses now house sleek restaurants along "Restaurant Row" where celebrity chefs create culinary magic. Art galleries and design studios fill converted brick buildings throughout this vibrant area. Union Park and Mary Bartelme Park offer green retreats amid the urban landscape. Getting around is simple with multiple train stations including Racine and Clinton. The area balances its industrial heritage with modern luxury in this walkable food lover's paradise.

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A river with a city skyline in the background, surrounded by green trees and grass.

A city skyline with a river, green spaces, and a baseball field.

A city skyline with tall buildings, a frozen lake, and leafless trees in a park.

A city skyline with high-rise buildings, a calm river reflecting the structures, and a park with trees and a walking path.

Lincoln Park

Lincoln Park blends urban energy with natural beauty along Chicago's stunning lakefront. The neighborhood's namesake 1,200-acre park offers endless recreation with a free zoo, conservatory, and scenic trails. Historic brownstones line tree-canopied streets, creating a charming residential atmosphere. Visitors can shop unique boutiques along Armitage Avenue or enjoy diverse dining options on Clark Street. The Chicago History Museum and North Avenue Beach provide cultural and outdoor attractions. Three convenient metro stations make exploring the rest of the city a breeze.

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Stay near popular Chicago attractions

An aerial view of a baseball stadium surrounded by urban buildings.

Wrigley Field

9.0/10 (11,704 reviews)

Step into baseball's living museum where ivy-covered walls and a hand-operated scoreboard create timeless charm. Experience the electrifying atmosphere of Cubs games in this century-old "Friendly Confines."

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A Ferris wheel and a carousel at a fairground.

Navy Pier

9.0/10 (24,140 reviews)

This historic Chicago waterfront landmark offers panoramic lake views from its iconic Centennial Wheel. Enjoy seasonal fireworks or interactive exhibits at the Children's Museum while exploring Navy Pier.

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A large stadium surrounded by a cityscape with modern buildings.

Soldier Field

8.8/10 (7,063 reviews)

Soldier Field blends historic neoclassical columns with modern design as home to the Chicago Bears. Experience the electric atmosphere of an NFL game or take a guided tour exploring its century of sporting heritage.

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A modern cityscape with tall buildings, a clear sky, and a tree-lined street.

McCormick Place

8.8/10 (9,822 reviews)

McCormick Place hosts major events like the Chicago Auto Show in its 2.6 million square feet of exhibition space. Arrive via the convenient Metra Electric Line station directly beneath the complex.

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A river with boats, surrounded by tall buildings and a clear sky.

Chicago Riverwalk

9.6/10 (13,574 reviews)

This 1.25-mile urban promenade showcases Chicago's stunning architecture alongside the river. Stroll past public art installations, dine at waterfront cafés, or catch the evening Art on theMART digital projection show.

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A cityscape with modern skyscrapers and the Cloud Gate sculpture.

Millennium Park

9.4/10 (30,446 reviews)

Discover Chicago's artistic heart at Millennium Park, home to the reflective Cloud Gate and interactive Crown Fountain. Stroll through Lurie Garden or catch a free concert at the Jay Pritzker Pavilion.

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A roller coaster in motion against a clear blue sky.

Six Flags Great America

8.6/10 (992 reviews)

This Midwest thrill-seeker's paradise boasts 15 roller coasters and immersive themed areas. Arrive at opening to conquer popular rides, or consider a Flash Pass to maximise your adventure.

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Chicago and related destinations

Towering skyscrapers frame the stunning Millennium Park where 'The Bean' reflects the city's vibrant energy. Cruise along the Chicago River for spectacular architecture views or catch a Cubs game at historic Wrigley Field.

See all hotels in Chicago

Top Chicago Hotel Reviews

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent

"The staff was very nice and helpful. Very happy with them and the room."

Hilton Chicago O'Hare Airport

8/10 Good

"Clean　room。nearly airport."

Hotel Riu Plaza Chicago

10/10 Excellent

"The rooms were super clean and the staff was very friendly and welcoming. Will definitely consider staying again the next time I visit Chicago."

Hyatt Regency Chicago

10/10 Excellent

"Everything you need restaurant , rentals car in same place make so easy to do ,discount in dinner was great."

Kasa Magnificent Mile Chicago

8/10 Good

"Comfortable, cozy. We just didn't know that we couldn't use the pool or the oven"

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"Beautiful hotel with an amazing pool! Spa services are fantastic!"

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"The complimentary breakfast was hot with multiple items to choose from and the night bar was very accommodating. The staff was pleasant and helpful. "

Holiday Inn & Suites Chicago - Downtown by IHG

8/10 Good

"Needed better cleaning of rooms"

More cheap stays in Chicago

Motel 6 Naperville, IL

1585 Naperville Wheaton Road Naperville IL

1.491.229 ₫

1.662.542 ₫ total

2 Sept - 3 Sept

includes taxes & fees

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

1.640.117 ₫

1.836.603 ₫ total

23 Aug - 24 Aug

includes taxes & fees

Comfort Inn Chicago Schaumburg - O'Hare Airport

1300 E Higgins Rd Schaumburg IL

2.172.569 ₫

2.498.019 ₫ total

7 Sept - 8 Sept

includes taxes & fees

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

2.857.820 ₫

3.397.662 ₫ total

31 Aug - 1 Sept

includes taxes & fees

7.6/10 Good! (2,755 reviews)

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL

2.972.550 ₫

3.750.107 ₫ total

9 Sept - 10 Sept

includes taxes & fees

8.2/10 Very good! (1,009 reviews)

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

4.326.886 ₫

5.144.236 ₫ total

30 Aug - 31 Aug

includes taxes & fees

8/10 Very good! (1,513 reviews)

Hotels in Chicago with star rating

Frequently asked questions

What's the seasonal weather in Chicago?

The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of -1°C. Average annual precipitation for Chicago is 1260 mm.

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More ways to book

Book Hotels in Chicago on Expedia.com

Find hotels in Chicago, IL from 1.662.542 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chicago (and vicinity)

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Chicago hotels

1. Hotel Riu Plaza Chicago

2. Hyatt Regency Chicago

3. InterContinental Chicago Magnificent Mile by IHG

4. LondonHouse Chicago, Curio Collection by Hilton

5. L7 Chicago by LOTTE

6. Eurostars Magnificent Mile

7. Hyatt Place Chicago/River North

8. Hilton Chicago/Magnificent Mile Suites

9. Crowne Plaza Chicago West Loop by IHG

10. The Royal Sonesta Chicago Downtown

11. Congress Plaza Hotel

12. citizenM Chicago Downtown

13. Sofitel Chicago Magnificent Mile

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

15. Hyatt House Chicago/West Loop-Fulton Market

16. Hilton Garden Inn Chicago Downtown Riverwalk

17. Hyatt Place Chicago/Downtown - The Loop

18. DoubleTree by Hilton Chicago - Magnificent Mile

19. Aloft by Marriott Chicago Mag Mile

20. Courtyard by Marriott Chicago Magnificent Mile

Holiday Rentals in Chicago

Kasa Magnificent Mile Chicago

Sentral Michigan Avenue

Level Chicago – Old Town

Ground Floor Studios in Chicago by 747 Lofts

The Neighborhood Hotel-Little Italy

McCormick Suites by Slumber Stay

Wrigleyville Suites

Kasa River North Chicago

Kasa South Loop Chicago

Kasa Lake Shore Chicago

Chicago Second Floor Studio by 747 Lofts

River West, Third Floor Chicago by 747 Lofts

Chicago Third Floor Studio by 747 Lofts

River West, Second Floor Chicago by 747 Lofts

Where to stay in Chicago

The Loop

River North

Magnificent Mile

West Loop

Lincoln Park

Stay near popular Chicago attractions

Wrigley Field

Navy Pier

Soldier Field

McCormick Place

Chicago Riverwalk

Millennium Park

Six Flags Great America

Chicago and related destinations

Top Chicago Hotel Reviews

Crowne Plaza Chicago West Loop by IHG

Hilton Chicago O'Hare Airport

Hotel Riu Plaza Chicago

Hyatt Regency Chicago

Kasa Magnificent Mile Chicago

InterContinental Chicago Magnificent Mile by IHG

The Chicago Hotel Collection - Magnificent Mile

Holiday Inn & Suites Chicago - Downtown by IHG

More cheap stays in Chicago

Motel 6 Naperville, IL

Red Roof Inn PLUS+ Chicago - Willowbrook

Comfort Inn Chicago Schaumburg - O'Hare Airport

Travelodge by Wyndham Downtown Chicago

Holiday Inn Chicago – Midway Airport S by IHG

Hampton Inn Chicago Downtown/Magnificent Mile

Hotels in Chicago with star rating

Frequently asked questions

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