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Beach access
Lakefront Rooftop Parking
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Mini-bar
- Terrace
The 3-bedroom Lakefront Rooftop Parking Chicago villa provides easy access to various city attractions, such as Saint Luke's Missionary Baptist Church, situated only 6 minutes' stroll away.
Lakefront Rooftop Parking
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Mini-bar
- Terrace
Lakefront Rooftop Parking
The 3-bedroom Lakefront Rooftop Parking Chicago villa provides easy access to various city attractions, such as Saint Luke's Missionary Baptist Church, situated only 6 minutes' stroll away.
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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 Wi-Fi, the 3-bedroom Hamaline Luxury Guest House Chicago villa is within 10 minutes' walk of 35th-Bronzeville-IIT underground station.
Hamaline Luxury Guest House
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Massage
- Garden area
Hamaline Luxury Guest House
Offering Wi-Fi, the 3-bedroom Hamaline Luxury Guest House Chicago villa is within 10 minutes' walk of 35th-Bronzeville-IIT underground station.
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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
Staying at Luxurious Gold Coast 4Br 4-Story Villa With Parking Sleeps 12 Guests Chicago, guests can easily reach the half - mile - long Navy Pier, located approximately a 25-minute walk away.
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
Staying at Luxurious Gold Coast 4Br 4-Story Villa With Parking Sleeps 12 Guests Chicago, guests can easily reach the half - mile - long Navy Pier, located approximately a 25-minute walk away.
A Home Away From Home!
- Cookware/ Kitchen utensils
- Flat-screen TV
- Tea and coffee facilities
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
- Flat-screen TV
- Tea and coffee facilities
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
Hosting up to 19 guests, Luxury 9 Bedroom Villa Mins From Downtown And The Lake Chicago offers a prime location around 6 km from sports attractions such as the baseball stadium "Wrigley Field".
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
Hosting up to 19 guests, Luxury 9 Bedroom Villa Mins From Downtown And The Lake Chicago offers a prime location around 6 km from sports attractions such as the baseball stadium "Wrigley Field".
Emmanuel Haven
- Cookware/ Kitchen utensils
- Flat-screen TV
- Ironing facilities
- Patio
Staying at the 5-bedroom Emmanuel Haven Villa Chicago, guests can easily reach Messiah and Saint Bartholomew Episcopal Church, located approximately 5 minutes' walk away.
Emmanuel Haven
- Cookware/ Kitchen utensils
- Flat-screen TV
- Ironing facilities
- Patio
Emmanuel Haven
Staying at the 5-bedroom Emmanuel Haven Villa Chicago, guests can easily reach Messiah and Saint Bartholomew Episcopal Church, located approximately 5 minutes' walk away.
Heavenly Abode
- Cookware/ Kitchen utensils
- Flat-screen TV
- Ironing facilities
- Tea and coffee facilities
Located about a 10-minute drive from the Frederick C. Frank Lloyd Wright's Robie House, the 1-bedroom Heavenly Abode Villa Chicago entices guests to relax in a Jacuzzi.
Heavenly Abode
- Cookware/ Kitchen utensils
- Flat-screen TV
- Ironing facilities
- Tea and coffee facilities
Heavenly Abode
Located about a 10-minute drive from the Frederick C. Frank Lloyd Wright's Robie House, the 1-bedroom Heavenly Abode Villa Chicago entices guests to relax in a Jacuzzi.
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Popular choice
Modern 3Bed 2Bath Cozy Ranch With Diy Art Porch
- Cookware/ Kitchen utensils
- Flat-screen TV
- Ironing facilities
- Patio
Located around 25 minutes' walk from the Monon Trail, Modern 3Bed 2Bath Cozy Ranch With Diy Art Porch Villa Calumet City provides access to various tourist attractions in the vicinity.
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
Located around 25 minutes' walk from the Monon Trail, Modern 3Bed 2Bath Cozy Ranch With Diy Art Porch Villa Calumet City provides access to various tourist attractions in the vicinity.
Modern 4Br Near Six Flags & Naval Base
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Patio
Situated approximately 10 minutes' drive from Howard Ganster Pool, the 5-bedroom Modern 4Br Near Six Flags & Naval Base Villa Gurnee 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
Modern 4Br Near Six Flags & Naval Base
Situated approximately 10 minutes' drive from Howard Ganster Pool, the 5-bedroom Modern 4Br Near Six Flags & Naval Base Villa Gurnee provides access to numerous tourist attractions in the area.
Urban Oasis In Chicago'S Best Suburb
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Luggage storage
Staying at Urban Oasis In Chicago'S Best Suburb Naperville villa, guests can easily reach Sky Zone Trampoline Park Amusement Center, located 3.4 km away.
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
Staying at Urban Oasis In Chicago'S Best Suburb Naperville villa, guests can easily reach Sky Zone Trampoline Park Amusement Center, located 3.4 km 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
The 3-bedroom 5 Star Luxury Stay Near Chicago O'Hare Des Plaines villa can host up to 10 guests, boasting a convenient location around a 15-minute drive from iconic cultural attractions such as Kohl Children's Museum.
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
The 3-bedroom 5 Star Luxury Stay Near Chicago O'Hare Des Plaines villa can host up to 10 guests, boasting a convenient location around a 15-minute drive from iconic cultural attractions such as Kohl Children's Museum.
Luxury 4Br Near Six Flags & Naval Base
- BBQ facilities
- Free parking
- Housekeeping
- Air conditioning
- Flat-screen TV
- Terrace
Situated nearly 5 minutes' walk from Clearview Park, the 4-bedroom Luxury 4Br Near Six Flags & Naval Base Villa Waukegan provides access to numerous tourist attractions in the area.
Luxury 4Br Near Six Flags & Naval Base
- BBQ facilities
- Free parking
- Housekeeping
- Air conditioning
- Flat-screen TV
- Terrace
Luxury 4Br Near Six Flags & Naval Base
Situated nearly 5 minutes' walk from Clearview Park, the 4-bedroom Luxury 4Br Near Six Flags & Naval Base Villa Waukegan provides access to numerous tourist attractions in the area.
Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Accommodating up to 4 guests, the 2-bedroom Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres New Buffalo is situated around 25 minutes on foot from renowned cultural sites such as New Buffalo Railroad Museum.
Guests can experience a relaxing stay with a sauna, or indulge in cycling and fisheries.
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
Accommodating up to 4 guests, the 2-bedroom Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres New Buffalo is situated around 25 minutes on foot from renowned cultural sites such as New Buffalo Railroad Museum.
Guests can experience a relaxing stay with a sauna, or indulge in cycling and fisheries.
Dogwood - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
The luxurious Dogwood - Upscale 2 Bedroom Villa At Petite Acres New Buffalo is located 15 minutes' drive from the outdoor Hesston Steam Museum and invites guests to join cycling and fisheries. Boasting a sauna, the 2-bedroom villa can accommodate up to 4 guests.
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
The luxurious Dogwood - Upscale 2 Bedroom Villa At Petite Acres New Buffalo is located 15 minutes' drive from the outdoor Hesston Steam Museum and invites guests to join cycling and fisheries. Boasting a sauna, the 2-bedroom villa can accommodate up to 4 guests.
Goldenrod - Upscale 2-Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Staying at the luxurious Goldenrod - Upscale 2-Bedroom Villa At Petite Acres New Buffalo, guests can easily reach the full - service Oselka's Snug Harbor Marina, located 25 minutes' walk away. Offering cycling and fisheries, the 2-bedroom villa is suitable for 4 guests.
Relax at a sauna, where you can enjoy the rest in full.
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
Staying at the luxurious Goldenrod - Upscale 2-Bedroom Villa At Petite Acres New Buffalo, guests can easily reach the full - service Oselka's Snug Harbor Marina, located 25 minutes' walk away. Offering cycling and fisheries, the 2-bedroom villa is suitable for 4 guests.
Relax at a sauna, where you can enjoy the rest in full.
Larkspur - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Guests of the 3-star Larkspur - Upscale 2 Bedroom Villa At Petite Acres New Buffalo hotel can enjoy access to Whittaker Woods Golf Course, located 3.9 km away. The inn features Wi-Fi, provided in public areas.
A casino, a sauna, and a golf course are available for guests' enjoyment. For lovers of active pastime there is cycling and fisheries.
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
Guests of the 3-star Larkspur - Upscale 2 Bedroom Villa At Petite Acres New Buffalo hotel can enjoy access to Whittaker Woods Golf Course, located 3.9 km away. The inn features Wi-Fi, provided in public areas.
A casino, a sauna, and a golf course are available for guests' enjoyment. For lovers of active pastime there is cycling and fisheries.
Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
The luxurious Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres New Buffalo is located 2.2 km from Galien River County Nature Park, giving access to various tourist spots nearby. Suitable for up to 4 guests, this 2-bedroom villa comes with a sauna.
The surroundings feature cycling and fisheries.
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
The luxurious Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres New Buffalo is located 2.2 km from Galien River County Nature Park, giving access to various tourist spots nearby. Suitable for up to 4 guests, this 2-bedroom villa comes with a sauna.
The surroundings feature cycling and fisheries.
Windflower - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
The luxurious Windflower - Upscale 2 Bedroom Villa At Petite Acres New Buffalo is located approximately a 25-minute walk from the full-service Oselka's Snug Harbor Marina and welcomes its guests to enjoy cycling and fisheries. The 2-bedroom and 1-bathroom villa welcomes up to 4 guests and provides a casino to entertain them.
A sauna are also offered for ultimate relaxation.
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
The luxurious Windflower - Upscale 2 Bedroom Villa At Petite Acres New Buffalo is located approximately a 25-minute walk from the full-service Oselka's Snug Harbor Marina and welcomes its guests to enjoy cycling and fisheries. The 2-bedroom and 1-bathroom villa welcomes up to 4 guests and provides a casino to entertain them.
A sauna are also offered for ultimate relaxation.
Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
The 2-bedroom Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres New Buffalo is located nearly a 25-minute walk from New Buffalo Railroad Museum and allows guests to enjoy cycling and fisheries.
A sauna are featured along with a fitness centre for guests' enjoyment.
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
The 2-bedroom Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres New Buffalo is located nearly a 25-minute walk from New Buffalo Railroad Museum and allows guests to enjoy cycling and fisheries.
A sauna are featured along with a fitness centre for guests' enjoyment.
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 |
7.4 / 10 (11 Reviews) |
From 301$ | |
| Hamaline Luxury Guest House |
7.1 / 10 (14 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 |
10.0 / 10 (6 Reviews) |
From 361$ |
More accommodations in Chicago
Frequently Asked Questions
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.
How can I easily get around Chicago during my stay?
Chicago offers a robust public transport system, including buses and trains. The 'L' train and buses can take you to key attractions efficiently.
Purchase a Ventra card for unlimited rides on public transport, a cost-effective choice for multiple trips.
Chicago and related destinations