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Beach access
Lakefront Rooftop Parking
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Mini-bar
- Terrace
Hosting a maximum of 16 guests, the 3-bedroom Lakefront Rooftop Parking Chicago villa is nearly a 10-minute ride from such educational sites as the leading research center "Oriental Institute Museum".
Lakefront Rooftop Parking
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Mini-bar
- Terrace
Lakefront Rooftop Parking
Hosting a maximum of 16 guests, the 3-bedroom Lakefront Rooftop Parking Chicago villa is nearly a 10-minute ride from such educational sites as the leading research center "Oriental Institute Museum".
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Beach access
Hamaline Luxury Guest House
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Massage
- Garden area
Offering temporary art galleries to make your visit more entertaining, the 1-bedroom Hamaline Luxury Guest House Chicago villa is situated in the Bronzeville district of Chicago.
Hamaline Luxury Guest House
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Massage
- Garden area
Hamaline Luxury Guest House
Offering temporary art galleries to make your visit more entertaining, the 1-bedroom Hamaline Luxury Guest House Chicago villa is situated in the Bronzeville district of Chicago.
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Guest favorite
Luxurious Gold Coast 4Br 4-Story Villa With Parking Sleeps 12 Guests
- Free parking
- Air conditioning
- Terrace
- Garden area
Located nearly 25 minutes' walk from the half-mile-long Navy Pier, Luxurious Gold Coast 4Br 4-Story Villa With Parking Sleeps 12 Guests Chicago provides access to various tourist attractions in the vicinity.
Luxurious Gold Coast 4Br 4-Story Villa With Parking Sleeps 12 Guests
- Free parking
- Air conditioning
- Terrace
- Garden area
Luxurious Gold Coast 4Br 4-Story Villa With Parking Sleeps 12 Guests
Located nearly 25 minutes' walk from the half-mile-long Navy Pier, Luxurious Gold Coast 4Br 4-Story Villa With Parking Sleeps 12 Guests Chicago provides access to various tourist attractions in the vicinity.
A Home Away From Home!
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Garden area
Situated only 1.3 km from the Bronzeville Children's Museum, A Home Away From Home! Chicago provides access to numerous tourist attractions in the area.
A Home Away From Home!
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Garden area
A Home Away From Home!
Situated only 1.3 km from the Bronzeville Children's Museum, A Home Away From Home! Chicago provides access to numerous tourist attractions in the area.
Luxury 9 Bedroom Villa Mins From Downtown And The Lake
- Free parking
- Air conditioning
- Flat-screen TV
- Heating
Luxury 9 Bedroom Villa Mins From Downtown And The Lake Chicago offers easy access to such tourist spots as Roman Susan, located just 6 minutes' walk away. Providing guests with Wi-Fi and complimentary private parking, the villa is 2.2 km from the energetic urban Kathy Osterman Beach.
Luxury 9 Bedroom Villa Mins From Downtown And The Lake
- Free parking
- Air conditioning
- Flat-screen TV
- Heating
Luxury 9 Bedroom Villa Mins From Downtown And The Lake
Luxury 9 Bedroom Villa Mins From Downtown And The Lake Chicago offers easy access to such tourist spots as Roman Susan, located just 6 minutes' walk away. Providing guests with Wi-Fi and complimentary private parking, the villa is 2.2 km from the energetic urban Kathy Osterman Beach.
Emmanuel Haven
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Patio
Boasting access to a patio, the 3-bedroom Emmanuel Haven Villa Chicago invites guests to visit the Frederick C. Frank Lloyd Wright's Robie House, located 4.8 km away.
Emmanuel Haven
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Patio
Emmanuel Haven
Boasting access to a patio, the 3-bedroom Emmanuel Haven Villa Chicago invites guests to visit the Frederick C. Frank Lloyd Wright's Robie House, located 4.8 km away.
Heavenly Abode
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Jacuzzi
Offering a location around 10 minutes' drive from the Frederick C. Frank Lloyd Wright's Robie House, Heavenly Abode Villa Chicago gives access to various tourist spots in the area.
The on-site treatment facilities include a hot tub.
Heavenly Abode
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Jacuzzi
Heavenly Abode
Offering a location around 10 minutes' drive from the Frederick C. Frank Lloyd Wright's Robie House, Heavenly Abode Villa Chicago gives access to various tourist spots in the area.
The on-site treatment facilities include a hot tub.
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Popular choice
Modern 3Bed 2Bath Cozy Ranch With Diy Art Porch
- Cookware/ Kitchen utensils
- Flat-screen TV
- Ironing facilities
- Patio
Situated around 25 minutes' walk from the Monon Trail, Modern 3Bed 2Bath Cozy Ranch With Diy Art Porch Villa Calumet City provides access to numerous tourist attractions in the area.
Modern 3Bed 2Bath Cozy Ranch With Diy Art Porch
- Cookware/ Kitchen utensils
- Flat-screen TV
- Ironing facilities
- Patio
Modern 3Bed 2Bath Cozy Ranch With Diy Art Porch
Situated around 25 minutes' walk from the Monon Trail, Modern 3Bed 2Bath Cozy Ranch With Diy Art Porch Villa Calumet City provides access to numerous tourist attractions in the area.
Modern 4Br Near Six Flags & Naval Base
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Patio
The 5-bedroom Modern 4Br Near Six Flags & Naval Base Villa Gurnee is located approximately 10 minutes by car from Howard Ganster Pool, giving access to various tourist spots nearby. The accommodation can host up to 10 guests, offering the opportunity to enjoy a patio.
Modern 4Br Near Six Flags & Naval Base
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Patio
Modern 4Br Near Six Flags & Naval Base
The 5-bedroom Modern 4Br Near Six Flags & Naval Base Villa Gurnee is located approximately 10 minutes by car from Howard Ganster Pool, giving access to various tourist spots nearby. The accommodation can host up to 10 guests, offering the opportunity to enjoy a patio.
Urban Oasis In Chicago'S Best Suburb
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Luggage storage
With the capacity to host 6 guests, Urban Oasis In Chicago'S Best Suburb Naperville villa is located 4.8 km from such significant cultural landmarks as the Dandelion Fountain.
Urban Oasis In Chicago'S Best Suburb
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Luggage storage
Urban Oasis In Chicago'S Best Suburb
With the capacity to host 6 guests, Urban Oasis In Chicago'S Best Suburb Naperville villa is located 4.8 km from such significant cultural landmarks as the Dandelion Fountain.
5 Star Luxury Stay Near Chicago O'Hare
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Garden area
Staying at 5 Star Luxury Stay Near Chicago O'Hare Des Plaines villa, guests can visit Lake Park Golf Course, which is approximately a 10-minute drive away.
5 Star Luxury Stay Near Chicago O'Hare
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Garden area
5 Star Luxury Stay Near Chicago O'Hare
Staying at 5 Star Luxury Stay Near Chicago O'Hare Des Plaines villa, guests can visit Lake Park Golf Course, which is approximately a 10-minute drive away.
Luxury 4Br Near Six Flags & Naval Base
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Terrace
Featuring a patio, Luxury 4Br Near Six Flags & Naval Base Villa Waukegan is situated 3.3 km from Lyons Woods Forest Preserve.
Luxury 4Br Near Six Flags & Naval Base
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Terrace
Luxury 4Br Near Six Flags & Naval Base
Featuring a patio, Luxury 4Br Near Six Flags & Naval Base Villa Waukegan is situated 3.3 km from Lyons Woods Forest Preserve.
Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Offering a location approximately 25 minutes on foot from the full-service Oselka's Snug Harbor Marina, Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres New Buffalo gives access to various tourist spots in the area.
Guests can experience a relaxing stay with a sauna, or indulge in cycling and fishing.
Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres
Offering a location approximately 25 minutes on foot from the full-service Oselka's Snug Harbor Marina, Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres New Buffalo gives access to various tourist spots in the area.
Guests can experience a relaxing stay with a sauna, or indulge in cycling and fishing.
Dogwood - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Situated a 10-minute drive from Galien River County Nature Park, Dogwood - Upscale 2 Bedroom Villa At Petite Acres New Buffalo offers a sauna for additional relaxation.
Guests can take advantage of cycling and fishing.
Dogwood - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Dogwood - Upscale 2 Bedroom Villa At Petite Acres
Situated a 10-minute drive from Galien River County Nature Park, Dogwood - Upscale 2 Bedroom Villa At Petite Acres New Buffalo offers a sauna for additional relaxation.
Guests can take advantage of cycling and fishing.
Goldenrod - Upscale 2-Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Featuring a sauna, Goldenrod - Upscale 2-Bedroom Villa At Petite Acres New Buffalo is 25 minutes' walk from the full-service Oselka's Snug Harbor Marina.
Goldenrod - Upscale 2-Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Goldenrod - Upscale 2-Bedroom Villa At Petite Acres
Featuring a sauna, Goldenrod - Upscale 2-Bedroom Villa At Petite Acres New Buffalo is 25 minutes' walk from the full-service Oselka's Snug Harbor Marina.
Larkspur - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Located 3.9 km from the Whittaker Woods Golf Course, Larkspur - Upscale 2 Bedroom Villa At Petite Acres New Buffalo provides access to various tourist attractions in the vicinity.
Guests can participate in cycling and fishing, or find relaxation at a sauna.
Larkspur - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Larkspur - Upscale 2 Bedroom Villa At Petite Acres
Located 3.9 km from the Whittaker Woods Golf Course, Larkspur - Upscale 2 Bedroom Villa At Petite Acres New Buffalo provides access to various tourist attractions in the vicinity.
Guests can participate in cycling and fishing, or find relaxation at a sauna.
Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Situated 2.2 km from Galien River County Nature Park, Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres New Buffalo provides access to numerous tourist attractions in the area.
Offering a sauna, guests can also enjoy cycling and fishing.
Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres
Situated 2.2 km from Galien River County Nature Park, Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres New Buffalo provides access to numerous tourist attractions in the area.
Offering a sauna, guests can also enjoy cycling and fishing.
Windflower - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Located approximately a 25-minute walk from the full - service Oselka's Snug Harbor Marina, Windflower - Upscale 2 Bedroom Villa At Petite Acres New Buffalo provides access to various tourist attractions in the vicinity.
A sauna are offered on-site.
Windflower - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Windflower - Upscale 2 Bedroom Villa At Petite Acres
Located approximately a 25-minute walk from the full - service Oselka's Snug Harbor Marina, Windflower - Upscale 2 Bedroom Villa At Petite Acres New Buffalo provides access to various tourist attractions in the vicinity.
A sauna are offered on-site.
Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Located nearly a 25-minute walk from the New Buffalo Railroad Museum, Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres New Buffalo entices guests to relax in a sauna.
Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres
Located nearly a 25-minute walk from the New Buffalo Railroad Museum, Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres New Buffalo entices guests to relax in a sauna.
Are you in a hurry?
Here is a quick list of hotels 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 |
7.6 / 10 (8 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 |
9.8 / 10 (4 Reviews) |
From 361$ |
More accommodations in Chicago
Frequently Asked Questions
Which Vacation homes have a lot of guest reviews?
Here are some Vacation homes that have the highest number of reviews:
Which vacation homes in Chicago offer parking facilities?
The Luxurious Gold Coast 4Br 4-Story Villa and Lakefront Rooftop Parking both provide convenient parking options. These homes make it easy to explore the city without worrying about parking fees.
If you're visiting on weekends, consider checking the street parking rules early to avoid fines during special events.
What vacation homes in Chicago are ideal for families?
The Modern 4Br Near Six Flags & Naval Base and the Luxury 9 Bedroom Villa Mins From Downtown and The Lake are great for families. They offer spacious rooms and are close to attractions.
Plan visits to Six Flags Great America during weekdays for shorter lines and less crowded experiences.
Which vacation homes in Chicago are suitable for extended stays?
The Urban Oasis In Chicago's Best Suburb and the A Home Away From Home! are ideal for long stays. They provide amenities like kitchens for convenient meal preparation.
Consider booking a home with laundry facilities for easy washing of clothes during longer visits.
Are there vacation homes in Chicago with balconies?
The Witch Hazel - Upscale 2 Bedroom Villa and Wild Indigo - Upscale 2 Bedroom Villa offer beautiful balconies. You can enjoy views of the surrounding neighborhood from these relaxing spots.
Check for rooms facing the lake or park for the best scenic views during your stay.
Which vacation homes in Chicago are dog-friendly?
The Dogwood - Upscale 2 Bedroom Villa and Hamaline Luxury Guest House welcome pets. They provide a comfortable space for both you and your furry friend.
Know the pet policies beforehand, as some may have weight limits or require additional fees.
What vacation homes in Chicago are near downtown?
The Luxury 9 Bedroom Villa and Luxurious Gold Coast 4Br 4-Story Villa are both close to downtown. You can easily walk or take public transit to major attractions.
Explore local dining options in downtown areas like River North for diverse food experiences.
Which Chicago vacation homes have pools?
The Modern 3Bed 2Bath Cozy Ranch and several luxury guest houses offer access to pools. These homes are perfect for cooling off during hot summer days.
Book early if you're planning a summer trip, as pool access may be popular among other guests.
How can I find the best vacation home in Chicago for my needs?
Identify what features you most desire, such as parking, pet-friendliness, or proximity to attractions. Research various listings and read guest reviews to help inform your decision.
Use filters on booking sites to narrow down options based on specific needs like family-sized accommodations.
What is the best time of year to book a Chicago vacation home?
Late spring and early fall are excellent times to visit Chicago, as the weather is enjoyable and there are numerous events. Prices may rise during summer, especially around festivals.
Consider visiting during the shoulder seasons in early June or late September for fewer crowds and pleasant weather.
Chicago and related destinations