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. Hyatt Regency Chicago

Downtown Chicago

Steve

7.360.712 ₫

9.675.646 ₫ total

includes taxes & fees

26 Sept - 27 Sept

2. Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

LISA

5.705.040 ₫

6.782.720 ₫ total

includes taxes & fees

20 Sept - 21 Sept

3. Hotel Riu Plaza Chicago

Downtown Chicago

Jarred

6.372.082 ₫

8.314.431 ₫ total

includes taxes & fees

20 Sept - 21 Sept

4. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Ann

8.185.941 ₫

9.732.264 ₫ total

includes taxes & fees

20 Sept - 21 Sept

5. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Darryl Halbert

7.260.960 ₫

9.540.173 ₫ total

includes taxes & fees

20 Sept - 21 Sept

6. L7 Chicago by LOTTE

Downtown Chicago

christina

6.696.952 ₫

7.962.007 ₫ total

includes taxes & fees

1 Oct - 2 Oct

7. Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Brian

5.258.762 ₫

6.252.141 ₫ total

includes taxes & fees

1 Oct - 2 Oct

8. Springhill Suites by Marriott Chicago Downtown/ River North

Downtown Chicago

Claudia

5.714.919 ₫

6.794.468 ₫ total

includes taxes & fees

27 Sept - 28 Sept

9. citizenM Chicago Downtown

Downtown Chicago

Germaine

5.004.876 ₫

5.950.297 ₫ total

includes taxes & fees

20 Sept - 21 Sept

Deluxe Suite, Multiple Beds, Lake View (King and Queen Bed)

10. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Downtown Chicago

Kelly

4.685.974 ₫

5.571.155 ₫ total

includes taxes & fees

27 Sept - 28 Sept

11. Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Kristeen

5.044.939 ₫

5.997.926 ₫ total

includes taxes & fees

20 Sept - 21 Sept

12. Hyatt Place Chicago/River North

Downtown Chicago

Eric

5.727.878 ₫

6.809.873 ₫ total

includes taxes & fees

27 Sept - 28 Sept

13. The Royal Sonesta Chicago Downtown

Downtown Chicago

ShaRona

6.327.408 ₫

8.352.478 ₫ total

includes taxes & fees

20 Sept - 21 Sept

14. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Phillip

4.254.145 ₫

5.058.051 ₫ total

includes taxes & fees

20 Sept - 21 Sept

15. Hyatt Centric The Loop Chicago

Downtown Chicago

Tamika

6.453.582 ₫

8.321.492 ₫ total

includes taxes & fees

27 Sept - 28 Sept

16. River Hotel

Downtown Chicago

steve

4.333.490 ₫

5.152.087 ₫ total

includes taxes & fees

27 Sept - 28 Sept

17. Swissotel - Chicago

Downtown Chicago

Bridgette

6.067.845 ₫

8.126.892 ₫ total

includes taxes & fees

27 Sept - 28 Sept

18. Silversmith Hotel Chicago Downtown

Downtown Chicago

Kun

4.738.718 ₫

6.424.879 ₫ total

includes taxes & fees

21 Sept - 22 Sept

19. DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

Madelyn

5.183.859 ₫

6.163.090 ₫ total

includes taxes & fees

20 Sept - 21 Sept

Presidential Suite, 1 King Bed, Accessible

1 King Bed, 1 Bedroom Suite | Living area

Presidential Suite, 1 King Bed, Accessible | Living room

20. LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Kamal

7.159.848 ₫

9.273.036 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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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 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.

A modern building with illuminated signage, surrounded by urban skyscrapers and a curved road with light trails.

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.

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.

A cityscape with tall buildings, including a historic tower and modern skyscrapers.

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

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 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 large metallic sphere sculpture in a public square surrounded by tall buildings.

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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A cityscape at night with illuminated buildings, a river, and a bridge.

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 city street at night with illuminated buildings, a prominent tower, and decorated trees.

Michigan Avenue

9.4/10 (15,813 reviews)

Stroll down this iconic Chicago boulevard lined with luxury boutiques and historic architecture. Enjoy world-class shopping, acclaimed restaurants, or explore nearby cultural spots like the Art Institute.

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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

Hampton Inn Chicago Downtown/Magnificent Mile

8/10 Good

"Everything was good"

River Hotel

10/10 Excellent

"This was our second stay at the River Hotel. Friendly, helpful staff. Clean rooms and property. Prime location for many activities in Chicago, as one can walk virtually everywhere. Many restaurants in the area in addition to attractions. A wonderful hotel."

Hilton Chicago O'Hare Airport

10/10 Excellent

"好"

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"Really good"

Hyatt Regency Chicago

10/10 Excellent

"Room was very nice and clean. Except for some hair in the bathtub from the previous guests"

Travelodge by Wyndham Downtown Chicago

10/10 Excellent

"TV didn't work"

Warwick Allerton - Chicago

10/10 Excellent

"It was our first time in Chicago, and we would definitely stay here again. The hotel is clean, quiet, and so pretty. (with an art deco vibe) It’s also located in a great area, very easily walkable to most shops/attractions/etc that were already on our list. The staff was so friendly. I wish I got the name of the lovely lady who was so generous to my friends and I. Overall such a nice comfy place to stay at!"

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent

"I really liked the fact they had water stations with bottles you could fill up"

The Wade

8/10 Good

"Staff was friendly, bar was nice, but don’t go to Timmy’s for food or good drinks. And don’t drink the water in the room"

More cheap stays in Chicago

Motel 6 Elk Grove Village, IL - O'Hare

2881 Touhy Ave Elk Grove Village IL

1.368.211 ₫

1.545.805 ₫ total

1 Oct - 2 Oct

includes taxes & fees

7.8/10 Good! (2,005 reviews)

Motel 6 Naperville, IL

1585 Naperville Wheaton Road Naperville IL

1.482.250 ₫

1.652.413 ₫ total

28 Sept - 29 Sept

includes taxes & fees

7.8/10 Good! (1,462 reviews)

Sleep Inn Midway Airport Bedford Park

6650 S Cicero Ave Chicago IL

2.755.991 ₫

3.237.738 ₫ total

4 Oct - 5 Oct

includes taxes & fees

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

4.185.757 ₫

4.976.515 ₫ total

29 Sept - 30 Sept

includes taxes & fees

7.6/10 Good! (2,829 reviews)

Holiday Inn Express Chicago - Magnificent Mile by IHG

640 N Wabash Ave Chicago IL

5.157.682 ₫

6.131.968 ₫ total

20 Sept - 21 Sept

includes taxes & fees

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

5.265.242 ₫

6.259.845 ₫ total

20 Sept - 21 Sept

includes taxes & fees

8/10 Very good! (1,599 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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Book Hotels in Chicago on Expedia.com

Find hotels in Chicago, IL from 1.545.805 ₫

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. Hyatt Regency Chicago

2. Hyatt Place Chicago/Downtown - The Loop

3. Hotel Riu Plaza Chicago

4. Hilton Vacation Club Hotel Blake Chicago

5. InterContinental Chicago Magnificent Mile by IHG

6. L7 Chicago by LOTTE

7. Hilton Chicago/Magnificent Mile Suites

8. Springhill Suites by Marriott Chicago Downtown/ River North

9. citizenM Chicago Downtown

10. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

11. Embassy Suites by Hilton Chicago Downtown River North

12. Hyatt Place Chicago/River North

13. The Royal Sonesta Chicago Downtown

14. Crowne Plaza Chicago West Loop by IHG

15. Hyatt Centric The Loop Chicago

16. River Hotel

17. Swissotel - Chicago

18. Silversmith Hotel Chicago Downtown

19. DoubleTree by Hilton Chicago - Magnificent Mile

20. LondonHouse Chicago, Curio Collection by Hilton

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

Millennium Park

Six Flags Great America

Chicago Riverwalk

Michigan Avenue

Chicago and related destinations

Top Chicago Hotel Reviews

Hampton Inn Chicago Downtown/Magnificent Mile

River Hotel

Hilton Chicago O'Hare Airport

The Chicago Hotel Collection Ambassador Gold Coast

Hyatt Regency Chicago

Travelodge by Wyndham Downtown Chicago

Warwick Allerton - Chicago

Club Quarters Hotel, Central Loop, Chicago

The Wade

More cheap stays in Chicago

Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Naperville, IL

Sleep Inn Midway Airport Bedford Park

Travelodge by Wyndham Downtown Chicago

Holiday Inn Express Chicago - Magnificent Mile by IHG

Hampton Inn Chicago Downtown/Magnificent Mile

Hotels in Chicago with star rating

Frequently asked questions

Explore a world of travel with Expedia

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