A cityscape with modern skyscrapers and a fountain in the foreground.

Vacation homes in Chicago

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Vacation homes in Chicago

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a vacation rental stay in Chicago on Hotels.com. These Chicago vacation rentals consistently deliver on quality, location and traveler experience. Last updated on September 11, 2026.

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

1. Kasa Magnificent Mile Chicago

Downtown Chicago

Premium Apartment, 1 Bedroom | Living area | 55-inch flat-screen TV with cable channels, TV

Breakfast, lunch, dinner and brunch served

2. Sentral Michigan Avenue

Downtown Chicago

CNY1,249

CNY1,663 total

includes taxes & fees

Sep 21 - Sep 22

Full-size fridge, microwave, oven, stovetop

3. Level Chicago – Old Town

Downtown Chicago

CNY2,032

CNY2,550 total

includes taxes & fees

Sep 27 - Sep 28

Deluxe Suite, 1 Bedroom, Kitchen (Two Beds, Washer/Dryer) | Living area | 45-inch LED TV with cable channels

4. The Gem Museum Suites

Downtown Evanston

CNY1,237

CNY1,417 total

includes taxes & fees

Sep 28 - Sep 29

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

Apartment, 2 Bedrooms (Queen) | Private kitchen | Coffee/tea maker, full-size fridge, microwave, oven

5. Kasa Lake Shore Chicago

Downtown Chicago

CNY1,308

CNY1,954 total

includes taxes & fees

Sep 20 - Sep 21

6. Wrigleyville Suites

Lakeview

CNY1,612

CNY1,892 total

includes taxes & fees

Oct 6 - Oct 7

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

Family Apartment, 3 Bedrooms, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | In-room dining

7. Kasa South Loop Chicago

Downtown Chicago

50-inch Smart TV with satellite channels

8. The Neighborhood Hotel-Little Italy

Near West Side

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

9. Kasa River North Chicago

Downtown Chicago

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

Studio, 1 Queen Bed with Sofa bed | Iron/ironing board (on request), WiFi (free)

Superior Apartment, 3 Bedrooms | Living area

10. McCormick Suites by Slumber Stay

Near South Side

11. River West, Third Floor Chicago by 747 Lofts

West Town

Studio | Iron/ironing board, WiFi (free)

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

12. Ground Floor Studios in Chicago by 747 Lofts

West Town

Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior

Design Apartment, Private Bathroom (The Oak Park Loft) | 2 bedrooms

13. The Oak Park Loft

Oak Park

14. Chicago Second Floor Studio by 747 Lofts

West Town

15. Chicago Third Floor Studio by 747 Lofts

West Town

16. River West, Second Floor Chicago by 747 Lofts

West Town

17. Stylish Apartment near Chicago Downtown

Bridgeport

Apartment, Private Bathroom | Terrace/patio

18. At Home in Oak Park

Oak Park

CNY1,526

CNY2,491 total

includes taxes & fees

Sep 21 - Sep 22

19. Cabin 105 by 747 Lofts

West Town

Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior

Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Lounge

Exclusive Room, Private Bathroom, Garden View (2nd Floor) | 4 bedrooms

20. Historic Oak Park Residence

Oak Park

CNY2,577

CNY3,695 total

includes taxes & fees

Oct 9 - Oct 10

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Top neighborhoods in Chicago

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

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

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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

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

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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

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

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

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, 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 an industrial zone into Chicago's culinary playground. Former warehouses now house art galleries and design studios, while "Restaurant Row" sizzles with celebrity chef hotspots and craft breweries. Visitors can explore converted lofts, browse boutique shops, or relax in Mary Bartelme Park between food adventures. Getting around is a breeze with three transit stations including Racine and Clinton on the Green Line. Most attractions sit within easy walking distance along wide sidewalks and bike lanes. Accommodation options feature industrial-chic hotels with exposed brick and modern amenities, perfectly matching the neighborhood's creative energy.

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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

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

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Top landmarks in Chicago

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

Wrigley Field

9.0/10 (11,704 reviews)

Why not catch an event at Wrigley Field, a major stadium in Lakeview. Let yourself be amazed at the art galleries in the area— your cultural tour starts here. If you think Wrigley Field is cool, you also might like United Center and Aragon Ballroom, both located nearby.

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A Ferris wheel and a carousel at a fairground.

Navy Pier

9.0/10 (24,140 reviews)

If you want to give your credit card some exercise, head out to Navy Pier, a popular place for shoppers in Downtown Chicago. Why not take a stroll along the riverfront and watch the sunset while you're here?

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A large stadium surrounded by a cityscape with modern buildings.

Soldier Field

8.8/10 (7,063 reviews)

Imagine soaking up the atmosphere at Soldier Field, a major stadium in Near South Side. Hotels.com travelers also like the art galleries, museums, and monuments in the area. If you think Soldier Field is cool, you also might like United Center and Wintrust Arena, both located nearby.

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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 is worth a pic or two when discovering Near South Side. Hotels.com travelers also like the art galleries, museums, and monuments in the area.

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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)

Millennium Park is worth a pic or two when discovering Downtown Chicago. Why not take a stroll along the riverfront and watch the sunset while you're here?

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

Chicago Riverwalk

9.6/10 (13,574 reviews)

Chicago Riverwalk is worth a pic or two when discovering Downtown Chicago. Why not take a stroll along the riverfront and watch the sunset while you're here?

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A busy urban street with a train crossing, tall buildings, and a tram.

Michigan Avenue

9.4/10 (15,813 reviews)

If you want to give your credit card some exercise, head out to Michigan Avenue, a popular place for shoppers in Downtown Chicago. Why not take a stroll along the riverfront and watch the sunset while you're here? It's also full of great shops and restaurants, so you can spend the afternoon having a wander. Splash some more cash at Shops at North Bridge, Harry Potter Shop Chicago, and Chicago Place Mall.

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A large, modern building with a curved facade and multiple vertical windows.

United Center

8.8/10 (4,269 reviews)

Why not catch an event at United Center, a major stadium in Near West Side. Let yourself be amazed at the museums and art galleries in the area too. If you think United Center is cool, you also might like Soldier Field and Wrigley Field, both located nearby.

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Chicago and related destinations

Towering skyscrapers create a skyline that seems to rise straight from Lake Michigan's blue waters. The Art Institute houses masterpieces while Millennium Park's reflective 'Bean' sculpture distorts the city in delightful ways. Navy Pier offers carnival-like fun with a giant Ferris wheel providing spectacular views. Wrigley Field remains gloriously old-school, where ivy-covered walls and hand-turned scoreboards transport baseball fans to another era. Deep-dish pizza at local institutions sparks fierce debates about whose crust reigns supreme. The Chicago River's architecture boat tours reveal how the city rebuilt itself after the Great Fire. Field Museum's Sue, the world's most complete T-Rex, stares down visitors with 65-million-year-old intensity.

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

About the destination

Chicago is a scenic place known for its skyscrapers, architecture, and riverfront. Nature lovers can explore top areas such as Millennium Park and Grant Park. Soldier Field and Navy Pier are other popular sights to see.

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