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Vacation homes near Oak Street

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Vacation homes near Oak Street

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 dining area with a wooden table and white chairs, large windows with blinds, and a vase with flowers on the table.

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

1. Kasa Magnificent Mile Chicago

Downtown Chicago

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

A balcony with a glass railing, a table, and four chairs.

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.

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

2. Sentral Michigan Avenue

Downtown Chicago

$143

$168 total

includes taxes & fees

Nov 9 - Nov 10

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.

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

3. Kasa Lake Shore Chicago

Downtown Chicago

$161

$241 total

includes taxes & fees

Nov 4 - Nov 5

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 row of treadmills in a gym with large windows and motivational posters on the walls.

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.

4. Kasa South Loop Chicago

Downtown Chicago

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

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.

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

5. Kasa River North Chicago

Downtown Chicago

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

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

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.

6. McCormick Suites by Slumber Stay

South Loop

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

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 high-rise building with multiple floors, large windows, and a modern architectural design.

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

7. Level Chicago – Old Town

Downtown Chicago

$303

$380 total

includes taxes & fees

Nov 2 - Nov 3

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.

8. Wrigleyville Suites

Lakeview

$149

$174 total

includes taxes & fees

Oct 27 - Oct 28

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 and a sign reading "747 LOFTS."

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

9. River West, Third Floor Chicago by 747 Lofts

West Town

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

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

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

A modern kitchen with white cabinets, a dining area with a white table and two chairs, and a large window providing natural light.

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

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

A modern kitchen with wooden cabinets, stainless steel appliances, and a bar stool.

11. Chicago Third Floor Studio by 747 Lofts

West Town

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

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

12. Chicago Second Floor Studio by 747 Lofts

West Town

A modern kitchen with a stainless steel refrigerator, wooden cabinets, and a window overlooking a cityscape.

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

13. River West, Second Floor Chicago by 747 Lofts

West Town

A modern interior with a large metallic chair, a glass table, and a black sofa.

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

A compact living space with a kitchenette, a bed, a sofa, and a floor lamp.

A compact hotel room with a bed, a small kitchenette, a TV, and a suitcase.

14. Cabin 105 by 747 Lofts

West Town

A modern bedroom with a bed, bedside table, lamp, and a view of the kitchen.

A modern kitchen with a microwave, stove, and refrigerator. There is a wooden cabinet wall, a small dining table, and a sofa.

A modern interior with a black leather sofa, a wooden cabinet, and a large pillar.

A modern office space with a reception desk, a large dark wall, and a sign for 'GINOSIAPARTELS'.

15. Ginosi 747 Apartel

West Town

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

A spacious lobby with a high ceiling, a reception desk, comfortable seating, and a large stained glass window.

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

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

16. The Gem Museum Suites

Downtown Evanston

$200

$229 total

includes taxes & fees

Nov 3 - Nov 4

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

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

A modern building with a sign reading "TOUS les JOUS" and a tree with yellow leaves in front.

17. The Neighborhood Hotel-Little Italy

Near West Side

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

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

A bedroom with a bed, a window, and a mirror with ornate frame.

18. The Oak Park Loft

Oak Park

$197

$337 total

includes taxes & fees

Oct 27 - Oct 28

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

A bedroom with a bed, bedside table, lamp, and a view of greenery outside.

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

19. At Home in Oak Park

Oak Park

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

A room with a bed, a chair, a fireplace, a door leading to another room, and a painting on the wall.

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

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

20. Historic Oak Park Home

Oak Park

$179

$316 total

includes taxes & fees

Oct 27 - Oct 28

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Other landmarks near Oak Street

A large indoor Christmas tree in a shopping mall.

900 North Michigan Shops

8.6/10 (55 reviews)

If you want to give your credit card some exercise, head out to 900 North Michigan Shops in Downtown Chicago. Why not take a stroll along the riverfront and watch the sunset while you're here? Splash some more cash at Michigan Avenue, Oak Street, and Water Tower Place.

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A tall skyscraper with a spire, a flagpole with an American flag, and a stone building with arched windows.

875 North Michigan Avenue

9.2/10 (2,926 reviews)

If you're planning a bit of sightseeing head to 875 North Michigan Avenue— just one of the monuments in Downtown Chicago. Why not take a stroll along the riverfront and watch the sunset while you're here?

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Topgolf Swing Suite

Downtown Chicago is home to Topgolf Swing Suite, so why not stop by during your stay in Chicago. Chicago has many other popular activities you might want to visit such as Soldier Field and Wrigley Field.

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Mariano Plaza

Mariano Plaza 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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The Drake

The Drake is a venue in Downtown Chicago.

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Fourth Presbyterian Church

10.0/10 (2 reviews)

Downtown Chicago is home to Fourth Presbyterian Church, so why not stop by during your stay in Chicago. Why not take a stroll along the riverfront and watch the sunset while you're here?

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360 CHICAGO

If you're planning a bit of sightseeing head to 360 CHICAGO— just one of the monuments in Downtown Chicago.

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Loyola University Museum of Art

9.0/10 (2 reviews)

Loyola University Museum of Art is just one of the attractions in Downtown Chicago, Chicago so you might want to stop by during your trip. Why not take a stroll along the riverfront and watch the sunset while you're here? If you want to experience more of the culture Chicago has to offer, head to Millennium Park, Navy Pier, and Soldier Field.

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About the destination

Where is Oak Street?

Oak Street is located in Downtown Chicago. It's in an artsy neighborhood well known for its great entertainment and architecture. If you'd like to find things to see and do in the area, you may want to check out Navy Pier and Soldier Field.

Things to See and Do near Oak Street

What to See near Oak Street

Michigan Avenue
Navy Pier
Soldier Field
McCormick Place
Wrigley Field

Things to Do near Oak Street

State Street
900 North Michigan Shops
Broadway Playhouse
Water Tower Place
Museum of Contemporary Art Chicago