A city skyline at dusk with illuminated buildings reflecting on the water.

Central Chicago Vacation Rentals

Where to?

Dates

November 2026

December 2026

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Central Chicago vacation rentals

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

1. Sentral Michigan Avenue

Downtown Chicago

Jeff

₩301,471 total

includes taxes & fees

Nov 24 - Nov 25

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

2. Kasa Lake Shore Chicago

Downtown Chicago

Jair

₩322,567 total

includes taxes & fees

Nov 22 - Nov 23

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

3. Level Chicago – Old Town

Downtown Chicago

Robert Edward

₩322,803 total

includes taxes & fees

Nov 23 - Nov 24

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

4. The Gem Museum Suites

Downtown Evanston

Ernest

₩307,702 total

includes taxes & fees

Nov 12 - Nov 13

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

5. Wrigleyville Suites

Lakeview

Francisco

₩187,419 total

includes taxes & fees

Nov 12 - Nov 13

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

6. At Home in Oak Park

Oak Park

Melissa

₩462,587 total

includes taxes & fees

Nov 12 - Nov 13

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

7. Historic Oak Park Home

Oak Park

Janette

₩478,782 total

includes taxes & fees

Nov 16 - Nov 17

A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

8. Classic Forest Park Foursquare < 1 Mi to Blue Line

Forest Park

₩637,768 total

includes taxes & fees

Nov 24 - Nov 25

A large brick house with a central chimney, a covered porch, and a brick pathway leading to the entrance.

9. The Oak Park Loft

Oak Park

Linda

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

10. Historic Oak Park Residence

Oak Park

Ann-Marie

View all properties

Find vacation rentals that suit your style

Top Central Chicago Hotel Reviews

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.

L7 CHICAGO by LOTTE HOTELS

Downtown Chicago

10/10 Excellent

Erin

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

Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

10/10 Excellent

Jennifer

A modern hotel lobby with a spiral staircase, seating areas, and large windows offering city views.

Residence Inn Chicago Downtown Magnificent Mile

Downtown Chicago

10/10 Excellent

Vickie

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

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

10/10 Excellent

blerina

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

Hotel Riu Plaza Chicago

Downtown Chicago

10/10 Excellent

We chose this hotel last minute and we were nervous because there were a couple recent negative reviews. There were 4 of us in our family and couldn't find anything negative to say about the hotel. The only disappointing fact was that the rooftop bar was not open but that wasn't a big deal. Everything was very clean. I actually wiped the floor in our room with a wet, white wash cloth, it was clean! There was no hair in the bathroom from a previous guest. There was no hair in the bed from a...

Donna

A hotel with a modern glass facade, signage for SpringHill Suites, and a well-lit entrance.

Springhill Suites by Marriott Chicago Downtown/ River North

Downtown Chicago

10/10 Excellent

Recently stayed at the Springhill Suites/River North. Could not have picked a better location for the first time in Chicago. Tons of local dining options. Close to landmarks. Easily walked to the Magnificient Mile(Michigan Ave) Walked to the subway to go to Wrigley Field and the United Center. Hotel was excellent. Clean, the staff was excellent in all areas. Free breakfast was fresh and good. Highly recommend overall.

Michael

A hotel with a classic facade, large windows, and flags.

Residence Inn Chicago Downtown/Loop

Downtown Chicago

10/10 Excellent

Sergio

A modern lobby with a reception desk, seating area, and a fireplace.

Aloft by Marriott Chicago Downtown River North

Downtown Chicago

10/10 Excellent

stephen

A modern interior with a geometric bookshelf filled with books, a bench, and a lamp.

Arlo Chicago

Downtown Chicago

10/10 Excellent

Arlo Chicago is in the perfect location for walkable access to so many Chicago sights, excellent food (please try the Broken English Taco Pub around the corner!), bars, shopping, etc. It was also very conveniently located to access the L when we needed to get to other parts of the city! The staff was BEYOND accommodating, friendly, and helpful. The room was clean and exceeded all comfort expectations! I also highly recommend the lobby bar for a great happy hour spot!!! Everyone at this hotel...

Lina

A modern hotel with a glass facade, a waterfront location, and a large Ferris wheel in the background.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

10/10 Excellent

Griffin

A modern hotel with a curved glass facade, a prominent 'SOFITEL' sign, and a colorful entrance area.

Sofitel Chicago Magnificent Mile

Downtown Chicago

10/10 Excellent

Denine

A spacious lobby with a long bar area, red curtains, and a patterned carpet.

Canopy by Hilton Chicago Central Loop

Downtown Chicago

10/10 Excellent

Chelsea

A corridor with ornate black metal railings and a patterned carpet.

Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

10/10 Excellent

Natalya

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

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

10/10 Excellent

Rosemary

Find out more about Central Chicago

Search for vacation rentals in Central Chicago on Expedia.co.kr! You can easily find your home rentals, villas, holiday apartments in Central Chicago using one of the methods below:

View our selection of featured holiday rentals in Central Chicago
Use the map to find apartments and other holiday homes in the Central Chicago neighbourhood you prefer
Enter your travel dates to view the best deals on holiday rentals in Central Chicago while they last

Look no further and take a look at our great range of rental properties in Central Chicago!

Central Chicago Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Central Chicago vacation rentals

1. Sentral Michigan Avenue

2. Kasa Lake Shore Chicago

3. Level Chicago – Old Town

4. The Gem Museum Suites

5. Wrigleyville Suites

6. At Home in Oak Park

7. Historic Oak Park Home

8. Classic Forest Park Foursquare < 1 Mi to Blue Line

9. The Oak Park Loft

10. Historic Oak Park Residence

Find vacation rentals that suit your style

Top Central Chicago Hotel Reviews

L7 CHICAGO by LOTTE HOTELS

10/10 Excellent

Find out more about Central Chicago

Explore a world of travel with Expedia