Chicago Holiday Rentals, Illinois: Private House Rentals

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Our top choices for Chicago hotels

A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

1. LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

James

5.181.778 ₫ total

includes taxes & fees

22 Nov - 23 Nov

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

2. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

tahira

4.924.519 ₫ total

includes taxes & fees

15 Nov - 16 Nov

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.

3. L7 Chicago by LOTTE

Downtown Chicago

Dimitri

4.454.433 ₫ total

includes taxes & fees

22 Nov - 23 Nov

A modern restaurant interior with a green wall, hanging lights, and a long dining area.

4. Hotel 505 River North

Downtown Chicago

Miya

5.712.054 ₫ total

includes taxes & fees

25 Nov - 26 Nov

The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

5. Hotel Riu Plaza Chicago

Downtown Chicago

JESUS VERA

4.659.476 ₫ total

includes taxes & fees

23 Nov - 24 Nov

A spacious bar area with high ceilings and large windows, offering views of a cityscape.

6. Hyatt Regency Chicago

Downtown Chicago

Addison

6.298.161 ₫ total

includes taxes & fees

23 Nov - 24 Nov

A dining area with a table set for four, large windows offering a cityscape view at dusk.

7. The Royal Sonesta Chicago Downtown

Downtown Chicago

osama

4.790.097 ₫ total

includes taxes & fees

24 Nov - 25 Nov

The Intercontinental hotel facade with a large American flag and a floral display.

8. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Nellie

6.526.630 ₫ total

includes taxes & fees

24 Nov - 25 Nov

A park with a stone staircase, trees, and a building with a curved facade in the background.

9. Fairmont Chicago at Millennium Park

Downtown Chicago

Ruby

7.035.987 ₫ total

includes taxes & fees

23 Nov - 24 Nov

A room with two chairs and a small table, a large window with a city view at night.

10. Eurostars Magnificent Mile

Downtown Chicago

Gabriela

4.424.876 ₫ total

includes taxes & fees

22 Nov - 23 Nov

A restaurant with wooden tables and chairs, large windows, and a green vine-covered ceiling.

11. Hyatt Place Chicago/River North

Downtown Chicago

Pamela

3.778.852 ₫ total

includes taxes & fees

22 Nov - 23 Nov

A dining table set for six with a cityscape view through large windows.

12. Swissotel - Chicago

Downtown Chicago

Oleg

5.385.081 ₫ total

includes taxes & fees

26 Nov - 27 Nov

13. Arlo Chicago

Downtown Chicago

Daniel

5.179.387 ₫ total

includes taxes & fees

26 Nov - 27 Nov

A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.

14. River Hotel

Downtown Chicago

Shelby

3.564.484 ₫ total

includes taxes & fees

22 Nov - 23 Nov

A modern building with a colorful facade and a red circular seating area.

15. citizenM Chicago Downtown

Downtown Chicago

Katarina

3.563.795 ₫ total

includes taxes & fees

23 Nov - 24 Nov

A modern building with a black facade and multiple windows. There is a sign for Hilton Garden Inn and a flagpole with flags.

16. Hilton Garden Inn Chicago Downtown Riverwalk

Downtown Chicago

David

3.753.660 ₫ total

includes taxes & fees

23 Nov - 24 Nov

A multi-level atrium with a central spiral staircase, multiple seating areas, and a pool.

17. Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Eliana

3.890.989 ₫ total

includes taxes & fees

22 Nov - 23 Nov

A snack bar with various packaged snacks and beverages.

18. Cambria Hotel Chicago Loop - Theatre District

Downtown Chicago

Vansh

3.416.326 ₫ total

includes taxes & fees

23 Nov - 24 Nov

A modern hotel lobby with a reception desk, marble flooring, and elegant chandeliers.

19. Silversmith Hotel Chicago Downtown

Downtown Chicago

William

4.290.556 ₫ total

includes taxes & fees

22 Nov - 23 Nov

A modern lobby with a grey sofa, checkered ottomans, and a coffee table. There are black chairs, a blue sofa, and a TV on a stand.

20. Aloft by Marriott Chicago Mag Mile

Downtown Chicago

Jena

3.363.175 ₫ total

includes taxes & fees

22 Nov - 23 Nov

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Holiday Rentals in Chicago

Aparthotel

A balcony with a table and chairs, a bottle of wine, and a glass of wine.

Kasa Magnificent Mile Chicago

Downtown Chicago

"Incredible stay, amazing location and great experience."

Aparthotel

A modern kitchen with a stove, dishwasher, and a dining area with a round table and chairs.

The Neighborhood Hotel-Little Italy

Near West Side

"Excellent hotel, will go often"

Aparthotel

A compact room with a bed, a sofa, a small kitchen area, and a TV mounted on the wall.

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

A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

Wrigleyville Suites

Lakeview

"What a gem right next to Wrigleyville Stadium! I had an emergency and needed somewhere to stay for two nights while my son was in the hospital. This was the perfect accommodation walkable to where I needed to go. Clean community townhome with lock off rooms, community kitchen and living room room – very lovely environment and excellent location. Walkable to many restaurants."

Aparthotel

A compact kitchen with a stainless steel refrigerator, wooden cabinets, a black leather sofa, and a small table.

River West, Third Floor Chicago by 747 Lofts

West Town

"Location was fantastic, bed the bed had a huge dip in the middle."

Aparthotel

A red brick building with a blue awning, a sign reading '747 N. MAY,' and a street view with parked cars.

Chicago Second Floor Studio by 747 Lofts

West Town

"i loved this place! would definitely come again"

Aparthotel

Chicago Third Floor Studio by 747 Lofts

West Town

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

Aparthotel

A red brick building with a blue awning and a sign reading "747 LOFTS."

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.

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

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

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.

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.

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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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

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

Top Chicago Hotel Reviews

L7 Chicago by LOTTE

10/10 Excellent

"Amazing hotel will stay again"

Sports Illustrated Resorts Chicago

8/10 Good

"Very convenient to an event at the Chicago Theater! Most comfortable bed / pillow combination and double paned windows helped for a great night sleep! Interesting layout with the bathroom in the middle of the space, but the shower felt great and the separate stall for the toilet is a nice feature. The lights were tricky to figure out and ended up getting woken up to a bright light after my husband couldn’t figure out how to turn them off. LOL Overall, great stay."

More cheap stays in Chicago

Comfort Inn Chicago Schaumburg - O'Hare Airport

1300 E Higgins Rd Schaumburg IL

2.333.118 ₫

2.682.618 ₫ total

2 Nov - 3 Nov

includes taxes & fees

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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Find hotels in Chicago, IL from 2.682.618 ₫

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Our top choices for Chicago hotels

1. LondonHouse Chicago, Curio Collection by Hilton

2. Hilton Vacation Club Hotel Blake Chicago

3. L7 Chicago by LOTTE

4. Hotel 505 River North

5. Hotel Riu Plaza Chicago

6. Hyatt Regency Chicago

7. The Royal Sonesta Chicago Downtown

8. InterContinental Chicago Magnificent Mile by IHG

9. Fairmont Chicago at Millennium Park

10. Eurostars Magnificent Mile

11. Hyatt Place Chicago/River North

12. Swissotel - Chicago

13. Arlo Chicago

14. River Hotel

15. citizenM Chicago Downtown

16. Hilton Garden Inn Chicago Downtown Riverwalk

17. Embassy Suites by Hilton Chicago Downtown River North

18. Cambria Hotel Chicago Loop - Theatre District

19. Silversmith Hotel Chicago Downtown

20. Aloft by Marriott Chicago Mag Mile

Holiday Rentals in Chicago

Kasa Magnificent Mile Chicago

Where to stay in Chicago

The Loop

River North

Magnificent Mile

West Loop

Lincoln Park

Stay near popular Chicago attractions

Wrigley Field

Chicago and related destinations

Top Chicago Hotel Reviews

L7 Chicago by LOTTE

More cheap stays in Chicago

Comfort Inn Chicago Schaumburg - O'Hare Airport

Hotels in Chicago with star rating

Frequently asked questions

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