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

Vacation homes in Chicago

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Vacation homes in Chicago

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

A modern living room with a sofa, a coffee table, a laptop, and a city view through large windows.

A high-rise building with multiple floors, large windows, and balconies.

A hotel lobby with a revolving door, a reception desk, and a waiting area with seating.

1. Kasa Magnificent Mile Chicago

Downtown Chicago

A modern building with the name 'SENIORAL' prominently displayed on the facade.

A bar area with stools, a counter with bottles, and a wall with a leafy design.

A modern kitchen with a large island, bar stools, and a view of the city skyline.

A modern kitchen with a built-in microwave, stove, and dishwasher, large windows with city views, and a dining area with a table and chairs.

2. Sentral Michigan Avenue

Downtown Chicago

$143

$168 total

includes taxes & fees

Nov 9 - Nov 10

A hotel lobby with sofas, a reception desk, a staircase, and a view of the outside.

A modern kitchen with a central island, stainless steel appliances, and a view of the city.

An outdoor seating area with modern furniture, surrounded by tall buildings.

3. Kasa Lake Shore Chicago

Downtown Chicago

$161

$241 total

includes taxes & fees

Nov 4 - Nov 5

A modern kitchen with a large island, bar stools, and a city view.

A spacious living area with a large sofa, a dining table, and a TV mounted on the wall.

A modern living room with a grey sectional sofa, a round coffee table, and a glass desk with a chair. Large windows offer a city view.

A modern dining area with a wooden table and chairs, a central sink, and large windows.

4. Level Chicago – Old Town

Downtown Chicago

$258

$327 total

includes taxes & fees

Nov 1 - Nov 2

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

A modern kitchen with dark wood flooring, stainless steel appliances, and a large island with a glass top.

A covered outdoor seating area with a wooden deck, black metal chairs, and a glass table.

A living room with a television, a sofa, a chair, and a coffee table. There are windows and a clock on the wall.

5. Wrigleyville Suites

Lakeview

$149

$174 total

includes taxes & fees

Oct 26 - Oct 27

A high-rise building with a modern architectural design, featuring a prominent red vertical stripe and multiple balconies.

A room with a white table and chair, a large green plant, a mirror, and a view of a balcony with a railing.

A modern living room with a grey sofa, a round coffee table, a TV on a wooden stand, and a large window with a city view.

A modern office space with a large window offering a city view, a round table with chairs, and abstract art on the wall.

6. Kasa South Loop Chicago

Downtown Chicago

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

A modern living room with a large window, a flat-screen TV, a grey armchair, a green sofa, and a small side table.

A modern kitchen with a dishwasher, a dining area with a round table, and a living space with a sofa and chairs.

7. The Neighborhood Hotel-Little Italy

Near West Side

A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

A compact living space with a kitchenette, a dining area, and a seating area with a TV.

A gym with various exercise equipment, large windows, and a television on the wall.

A patio area with outdoor seating and a view of a park with trees and a lawn.

8. The Gem Museum Suites

Downtown Evanston

$200

$229 total

includes taxes & fees

Nov 3 - Nov 4

A modern kitchen with a bar area, large windows, and a view of the city.

A modern living room with a sofa, chairs, a coffee table, and a dining area with a table and chairs.

A rooftop patio with outdoor furniture, a grill, and string lights against a sunset cityscape.

A modern apartment with a blue sofa, a bed, a kitchen, and a large window.

9. McCormick Suites by Slumber Stay

South Loop

A modern lobby with seating areas, a large pillar, and glass doors leading outside.

A modern conference room with a large table, six chairs, and a city view through large windows.

A modern lounge area with a geometric ceiling, large windows, and a bar with stools.

A rooftop pool area with sun loungers and a modern building in the background.

10. Kasa River North Chicago

Downtown Chicago

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

A compact bedroom with a bed, a small kitchenette, a sofa, and a dining table.

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

A modern hotel room with a large bed, a seating area, and a suitcase.

11. River West, Third Floor Chicago by 747 Lofts

West Town

A compact kitchen with stainless steel appliances, wooden cabinets, and a tiled backsplash.

A compact living space with a kitchenette, a sofa, a bed, and a television mounted on the wall.

A compact living space with a kitchenette, a dining area, and a bed.

12. Ground Floor Studios in Chicago by 747 Lofts

West Town

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

A modern bedroom with a bed, a black leather sofa, and large windows offering city views.

A modern hotel room with a bed, a sofa, a small table, and a kitchenette.

A modern hotel room with a bed, a sofa, a small table, a suitcase, and large windows offering city views.

13. Chicago Third Floor Studio by 747 Lofts

West Town

A two-story house with a brick exterior, a sloped roof, and a front porch.

A hallway with wooden flooring, white walls, and a ceiling light.

A fenced tennis court with a bicycle parked nearby, surrounded by trees and a clear sky.

14. At Home in Oak Park

Oak Park

A modern kitchen with wooden cabinets, a microwave, and a stove. There is a purple sofa and a small table with chairs. A suitcase is on the floor next to the sofa.

A modern hotel room with a bed, a desk, a chair, a sofa, and a TV mounted on the wall.

A modern hotel room with a bed, a desk, a chair, a sofa, a large window, and a flat-screen TV.

A compact kitchen with modern appliances, a dining area with bar stools, and a small bed.

15. Chicago Second Floor Studio by 747 Lofts

West Town

A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

A cozy loft-style room with a bed, sofa, and dining area, featuring a wooden ceiling and a stained glass light fixture.

A dining area with a round table, blue chairs, and a chandelier.

16. The Oak Park Loft

Oak Park

$197

$337 total

includes taxes & fees

Oct 27 - Oct 28

17. River West, Second Floor Chicago by 747 Lofts

West Town

A living room with a sofa, a glass coffee table, a lamp, a ceiling fan, and a window with blinds.

A wooden deck with a table and chairs, a covered area, and a brick building in the background.

A living room with a round glass table, a framed picture, a TV on the wall, and a door leading to another room.

A modern kitchen with wooden cabinets, stainless steel appliances, a glass island, and a window with blinds.

18. Peaceful One Bedroom Home Near Chicago

Forest Park

A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

A two-story house with a steeply pitched roof, a chimney, and a well-maintained garden with various shrubs and a tall coniferous tree.

A dining area with a long wooden table, chairs, a chandelier, and a window with curtains.

A modern kitchen with white cabinets, a stainless steel stove, and a large window.

19. Historic Oak Park Home

Oak Park

$179

$316 total

includes taxes & fees

Oct 27 - Oct 28

A building with a white exterior and a tree with white blossoms in front.

A room with a ceiling fan, a large rug, a rocking chair, a sofa, and a table.

A bedroom with a bed, a radiator, a window with curtains, a mirror, and a rocking elephant toy.

A dining area with a round table, four chairs, a chandelier, a cabinet with decorative items, and a window with curtains.

20. Historic Oak Park Residence

Oak Park

$320

$477 total

includes taxes & fees

Oct 27 - Oct 28

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

A river with a yellow boat and a white yacht. In the background, there are tall buildings and a bridge.

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

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

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.

A coastal cityscape with a long beach, dense urban buildings, and a clear blue sea.

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, including a historic tower and modern skyscrapers.

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

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 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 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 modern glass building with a curved roof, surrounded by a landscaped garden and a water feature.

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 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 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 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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A city street at night with illuminated buildings, a snow-covered sidewalk, and light trails from moving vehicles.

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, Water Tower Place, and 900 North Michigan Shops.

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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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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.