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Mar 23 - Mar 24 ·
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Chicago Vacation Rentals

Chicago
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Over 1,040 stays assessed to highlight the standout picks
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Luxury Vacation Rentals Chicago

Navigation

1. Lakefront Rooftop Parking

2. Hamaline Luxury Guest House

3. Luxurious Gold Coast 4Br 4-Story Villa With Parking Sleeps 12 Guests

4. A Home Away From Home!

Cheap Vacation Rentals in Chicago Illinois

5. Luxury 9 Bedroom Villa Mins From Downtown And The Lake

6. Emmanuel Haven

7. Heavenly Abode

Pet Friendly Vacation Rentals Chicago

8. Modern 3Bed 2Bath Cozy Ranch With Diy Art Porch

9. Modern 4Br Near Six Flags & Naval Base

10. Urban Oasis In Chicago'S Best Suburb

  • Beach access
Hotel Image Hotel Image

Lakefront Rooftop Parking

7346 South South Shore Drive
14.2 km (8.8 mi) from city center
204
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Mini-bar
  • Terrace
7.6
10 reviews
~ US$301 / night

Lakefront Rooftop Parking

14.2 km (8.8 mi) from city center
204
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Mini-bar
  • Terrace

Lakefront Rooftop Parking

7.6
10 reviews
Average price US$ 301 / night
  • Beach access
Hotel Image Hotel Image

Hamaline Luxury Guest House

76 East 37Th Street
5.6 km (3.5 mi) from city center
1200
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Massage
  • Garden area
7.8
4 reviews
~ US$336 / night

Hamaline Luxury Guest House

5.6 km (3.5 mi) from city center
1200
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Massage
  • Garden area

Hamaline Luxury Guest House

7.8
4 reviews
Average price US$ 336 / night
Popular Vacation rentals destinations
Orlando
Miami Beach
Dubrovnik
Kissimmee
Rio de Janeiro
  • Guest favorite
Hotel Image Hotel Image

Luxurious Gold Coast 4Br 4-Story Villa With Parking Sleeps 12 Guests
111 West Elm Street
3.0 km (1.9 mi) from city center
274
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Terrace
  • Garden area
9.2
8 reviews
~ US$764 / night

Luxurious Gold Coast 4Br 4-Story Villa With Parking Sleeps 12 Guests
3.0 km (1.9 mi) from city center
274
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Terrace
  • Garden area

Luxurious Gold Coast 4Br 4-Story Villa With Parking Sleeps 12 Guests
9.2
8 reviews
Average price US$ 764 / night

Cheap Vacation Rentals in Chicago Illinois

Hotel Image Hotel Image

A Home Away From Home!

8858 South Constance Avenue
16.6 km (10.3 mi) from city center
161
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Garden area
7.4
7 reviews

A Home Away From Home!

16.6 km (10.3 mi) from city center
161
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Garden area

A Home Away From Home!

7.4
7 reviews
Hotel Image Hotel Image

Luxury 9 Bedroom Villa Mins From Downtown And The Lake

6417 North Magnolia Avenue
13.7 km (8.5 mi) from city center
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Heating
9
1 reviews

Luxury 9 Bedroom Villa Mins From Downtown And The Lake

13.7 km (8.5 mi) from city center
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Heating

Luxury 9 Bedroom Villa Mins From Downtown And The Lake

9
1 reviews
Hotel Image Hotel Image

Emmanuel Haven

8139 South Blackstone Avenue
15.0 km (9.3 mi) from city center
279
  • Cookware/ Kitchen utensils
  • Free parking
  • Security
  • Air conditioning
  • Flat-screen TV
  • Patio
5.5
2 reviews

Emmanuel Haven

15.0 km (9.3 mi) from city center
279
  • Cookware/ Kitchen utensils
  • Free parking
  • Security
  • Air conditioning
  • Flat-screen TV
  • Patio

Emmanuel Haven

5.5
2 reviews

Pet Friendly Vacation Rentals Chicago

Hotel Image Hotel Image

Heavenly Abode

8157 South Dorchester Avenue
15.0 km (9.3 mi) from city center
279
  • Cookware/ Kitchen utensils
  • Free parking
  • Security
  • Air conditioning
  • Flat-screen TV
  • Jacuzzi

Heavenly Abode

15.0 km (9.3 mi) from city center
279
  • Cookware/ Kitchen utensils
  • Free parking
  • Security
  • Air conditioning
  • Flat-screen TV
  • Jacuzzi

Heavenly Abode

Vacation rentals near Chicago

These options match your search but are within a one-hour drive of the city (up to 80 km / 50 mi).

  • Popular choice
Hotel Image Hotel Image

Modern 3Bed 2Bath Cozy Ranch With Diy Art Porch

1313 Gordon Avenue
32.2 km (20.0 mi) from Chicago
93
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Live entertainment
  • Garden area
8.4
26 reviews

Modern 3Bed 2Bath Cozy Ranch With Diy Art Porch

32.2 km (20.0 mi) from Chicago
93
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Live entertainment
  • Garden area

Modern 3Bed 2Bath Cozy Ranch With Diy Art Porch

8.4
26 reviews
Hotel Image Hotel Image

Modern 4Br Near Six Flags & Naval Base

4226 Bennett Avenue
58.2 km (36.2 mi) from Chicago
2400
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Patio
9.7
4 reviews
~ US$361 / night

Modern 4Br Near Six Flags & Naval Base

58.2 km (36.2 mi) from Chicago
2400
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Patio

Modern 4Br Near Six Flags & Naval Base

9.7
4 reviews
Average price US$ 361 / night

Chicago Vacation Rentals Oceanfront

Hotel Image Hotel Image

Urban Oasis In Chicago'S Best Suburb

905 Bradford Drive
48.1 km (29.9 mi) from Chicago
167
  • Cookware/ Kitchen utensils
  • Free parking
  • Security
  • Air conditioning
  • Flat-screen TV
  • Luggage storage
9.8
5 reviews

Urban Oasis In Chicago'S Best Suburb

48.1 km (29.9 mi) from Chicago
167
  • Cookware/ Kitchen utensils
  • Free parking
  • Security
  • Air conditioning
  • Flat-screen TV
  • Luggage storage

Urban Oasis In Chicago'S Best Suburb

9.8
5 reviews
Hotel Image Hotel Image

5 Star Luxury Stay Near Chicago O'Hare

320 Bellaire Avenue
26.8 km (16.7 mi) from Chicago
186
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Garden area
10
1 reviews

5 Star Luxury Stay Near Chicago O'Hare

26.8 km (16.7 mi) from Chicago
186
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Garden area

5 Star Luxury Stay Near Chicago O'Hare

10
1 reviews
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Luxury 4Br Near Six Flags & Naval Base

1417 North Mcaree Road
59.0 km (36.7 mi) from Chicago
162
  • Cookware/ Kitchen utensils
  • Free parking
  • Security
  • Air conditioning
  • Flat-screen TV
  • Terrace
10
1 reviews

Luxury 4Br Near Six Flags & Naval Base

59.0 km (36.7 mi) from Chicago
162
  • Cookware/ Kitchen utensils
  • Free parking
  • Security
  • Air conditioning
  • Flat-screen TV
  • Terrace

Luxury 4Br Near Six Flags & Naval Base

10
1 reviews

Chicago Vacation Rentals with Private Pool

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Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres

1109 East Buffalo Street
75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres

75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres

Hotel Image Hotel Image

Dogwood - Upscale 2 Bedroom Villa At Petite Acres

1109 East Buffalo Street
75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Dogwood - Upscale 2 Bedroom Villa At Petite Acres

75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Dogwood - Upscale 2 Bedroom Villa At Petite Acres

Hotel Image Hotel Image

Goldenrod - Upscale 2-Bedroom Villa At Petite Acres

1109 East Buffalo Street
75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Goldenrod - Upscale 2-Bedroom Villa At Petite Acres

75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Goldenrod - Upscale 2-Bedroom Villa At Petite Acres

Hotel Image Hotel Image

Larkspur - Upscale 2 Bedroom Villa At Petite Acres

1109 East Buffalo Street
75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Larkspur - Upscale 2 Bedroom Villa At Petite Acres

75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Larkspur - Upscale 2 Bedroom Villa At Petite Acres

Hotel Image Hotel Image

Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres

1109 East Buffalo Street
75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres

75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres

Hotel Image Hotel Image

Windflower - Upscale 2 Bedroom Villa At Petite Acres

1109 East Buffalo Street
75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Windflower - Upscale 2 Bedroom Villa At Petite Acres

75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Windflower - Upscale 2 Bedroom Villa At Petite Acres

Hotel Image Hotel Image

Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres

1109 East Buffalo Street
75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres

75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres

Hotel Image Hotel Image

Woodsage - Upscale 2 Bedroom Villa At Petite Acres

1109 East Buffalo Street
75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Woodsage - Upscale 2 Bedroom Villa At Petite Acres

75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Woodsage - Upscale 2 Bedroom Villa At Petite Acres

Are you in a hurry?

Here is a quick list of Vacation Rentals in Chicago, selected based on their rating

Name of hotel Accommodation Rating Price, $
Lakefront Rooftop Parking

7.6 / 10

(10 Reviews)

 From 301$
Hamaline Luxury Guest House

7.8 / 10

(4 Reviews)

 From 336$
Luxurious Gold Coast 4Br 4-Story Villa With Parking Sleeps 12 Guests

9.2 / 10

(8 Reviews)

 From 764$
Modern 4Br Near Six Flags & Naval Base

9.7 / 10

(4 Reviews)

 From 361$

When you are planning a trip to Chicago, there are many different types of lodging to choose from. You can stay in a hotel, motel, hostel, or bed and breakfast. But, if you are looking for something more spacious and comfortable than a hotel room, you may want to consider a vacation rental.

A vacation rental is a home or apartment that is rented for short-term stays. It can be a great option for families, groups, or couples. Vacation rentals come in all shapes and sizes, and there are many to choose from in the Chicago area.

Some people may be hesitant to choose a vacation rental over a hotel, but there are many reasons why a rental can be a better choice. For starters, vacation rentals are often more affordable than hotels. They also offer more space and privacy, and many come with fully equipped kitchens. This can be a great way to save money on meals while you are traveling.

Another advantage of choosing a vacation rental is that you can often find properties in desirable locations. Many vacation rentals are located in neighborhoods that are close to popular tourist destinations, restaurants, and shopping areas. This can be a great way to enjoy all that Chicago has to offer while still having a comfortable place to come home to at the end of the day.

Frequently Asked Questions

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Our guests usually stay in high-rated holiday houses in such districts as — West Town, South Loop and Lincoln Park.

What are the finest Chicago holiday rentals to stay with pets?

According to our guests reviews: Penthouse Level, Stunning Wrigley Stay is the best pet-friendly accommodation in Chicago to stay with your little friends.

What are the best budget holiday rentals to stay in Chicago?

Some of the top cheap apartments are:
5430 Happy Home from 98US$/night
✪ Cozy 1 Bedroom Close To Downtown ✪ from 139US$/night
Find out more favoured cheap places to stay here.

How much does a 2-bedroom holiday house cost for a week?

A 2-bedroom holiday home in Chicago costs about 1190US$. Check this popular option: Home With Spacious Yard 14 Mi To Dtwn.

How much does a 3-bedroom holiday house cost for a week?

A 3-bedroom house for rent costs approximately 134US$ per week try this popular option — Escape Near Navy Pier And Shedd Aquarium!.

What are the top apartments close to a beach?

If you are searching for a beach villa, Old Town-Gold Coast Amazing 3 Bedroom Home/ Free Parking/ Breakfast/ Backyard/ Walk Everywhere/ Pets Ok is a great option to consider.

What are the top-ranked holiday rentals with swimming pools in Chicago?

To swim and relax around the pool without leaving your holiday rental, stay at Global Luxury Suites In Downtown, 3Br Premium Executive Penthouse W/ Pool & Parking, or Oakwood 200 Squared. Other popular holiday places with swimming pools you can check here.

What are the best holiday rentals with free wifi in Chicago?

Global Luxury Suites In Downtown and 5430 Happy Home are the best holiday accommodations providing free wifi.

What are the best holiday rentals near The Art Institute of Chicago?

3Br Premium Executive Penthouse W/ Pool & Parking is the most popular holiday accommodation not far from The Art Institute of Chicago, one of the top Chicago attractions.

What are the best Chicago holiday rentals with free parking?

If you want to park your car on site, check ✪ Cozy 1 Bedroom Close To Downtown ✪, in which prices start from 139US$.

Location

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