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Best-rated
The Avondale Guesthouse
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Terrace
Staying at the 6-room The Avondale Guesthouse Chicago villa, guests can easily reach the Dill Pickle Food Co-op, located 25 minutes' walk away.
The Avondale Guesthouse
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Terrace
The Avondale Guesthouse
Staying at the 6-room The Avondale Guesthouse Chicago villa, guests can easily reach the Dill Pickle Food Co-op, located 25 minutes' walk away.
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Great deal
Stunning Condo #2 - Downtown River North
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Patio
The 3-bedroom Stunning Condo #2 - Downtown River North Chicago villa provides easy access to various city attractions, such as the long-standing Carl Hammer Gallery, situated a mere 6 minutes' walk away.
Stunning Condo #2 - Downtown River North
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Patio
Stunning Condo #2 - Downtown River North
The 3-bedroom Stunning Condo #2 - Downtown River North Chicago villa provides easy access to various city attractions, such as the long-standing Carl Hammer Gallery, situated a mere 6 minutes' walk away.
Lincoln Park Living - 3 Queen Beds - Sleeps 6
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Patio
The 1-bedroom Lincoln Park Living - 3 Queen Beds - Sleeps 6 Chicago villa offers proximity to nearby tourist spots, such as Rosa's Lounge, situated about a 5-minute walk away.
Lincoln Park Living - 3 Queen Beds - Sleeps 6
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Patio
Lincoln Park Living - 3 Queen Beds - Sleeps 6
The 1-bedroom Lincoln Park Living - 3 Queen Beds - Sleeps 6 Chicago villa offers proximity to nearby tourist spots, such as Rosa's Lounge, situated about a 5-minute walk away.
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Beach access
Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Live entertainment
- Terrace
The 4-bedroom Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find Villa Chicago boasts a location a mere 6 minutes on foot from North Shore 7th Day Adventist Church and offers guests to enjoy a games room. Located 4.9 km from the baseball stadium "Wrigley Field", the Chicago villa features badminton and darts.
Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Live entertainment
- Terrace
Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find
The 4-bedroom Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find Villa Chicago boasts a location a mere 6 minutes on foot from North Shore 7th Day Adventist Church and offers guests to enjoy a games room. Located 4.9 km from the baseball stadium "Wrigley Field", the Chicago villa features badminton and darts.
Lincoln Park Living - Suite 2
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Patio
Located a mere 6 minutes' walk from Holy Covenant United Methodist Church, the 2-bedroom Lincoln Park Living - Suite 2 Chicago villa offers quick access to various city attractions in the vicinity.
Lincoln Park Living - Suite 2
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Patio
Lincoln Park Living - Suite 2
Located a mere 6 minutes' walk from Holy Covenant United Methodist Church, the 2-bedroom Lincoln Park Living - Suite 2 Chicago villa offers quick access to various city attractions in the vicinity.
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Beach access
Designer Themed 4 Bedroom In Best Location With Patio And Fireplace
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Live entertainment
- Terrace
Designer Themed 4 Bedroom In Best Location With Patio And Fireplace Chicago villa, located 6 minutes' walk from Plum Market Old Town, can host up to 14 guests.
Designer Themed 4 Bedroom In Best Location With Patio And Fireplace
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Live entertainment
- Terrace
Designer Themed 4 Bedroom In Best Location With Patio And Fireplace
Designer Themed 4 Bedroom In Best Location With Patio And Fireplace Chicago villa, located 6 minutes' walk from Plum Market Old Town, can host up to 14 guests.
Stunning Duplex Condo #1 - Downtown River North
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Patio
Staying at Stunning Duplex Condo #1 - Downtown River North Chicago villa, guests can visit Millennium Public Park, which is about a 25-minute walk away. This Chicago holiday home hosts up to 10 guests and invites them to unwind on a patio.
Stunning Duplex Condo #1 - Downtown River North
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Patio
Stunning Duplex Condo #1 - Downtown River North
Staying at Stunning Duplex Condo #1 - Downtown River North Chicago villa, guests can visit Millennium Public Park, which is about a 25-minute walk away. This Chicago holiday home hosts up to 10 guests and invites them to unwind on a patio.
Lincoln Park Living - Suite 1
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Patio
Staying at the 2-bedroom Lincoln Park Living - Suite 1 Chicago villa, guests can easily reach the Margaret Donahue Park, located 19 minutes' walk away.
Lincoln Park Living - Suite 1
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Patio
Lincoln Park Living - Suite 1
Staying at the 2-bedroom Lincoln Park Living - Suite 1 Chicago villa, guests can easily reach the Margaret Donahue Park, located 19 minutes' walk away.
Victorian Mansion In Garfield Park
- Cookware/ Kitchen utensils
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Car park
Charges may apply
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Terrace
Situated 14 minutes' walk from the 184-acre Garfield Park Conservatory, Victorian Mansion In Garfield Park Villa Chicago entices guests to explore various tourist attractions in the area.
Victorian Mansion In Garfield Park
- Cookware/ Kitchen utensils
-
Car park
Charges may apply
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Terrace
Victorian Mansion In Garfield Park
Situated 14 minutes' walk from the 184-acre Garfield Park Conservatory, Victorian Mansion In Garfield Park Villa Chicago entices guests to explore various tourist attractions in the area.
Spacious Row Home Next Transit Near Downtown W Parking
- Picnic area/ Tables
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Garden area
Spacious Row Home Next Transit Near Downtown W Parking Chicago can host up to 16 guests, boasting a prime location 7 km from iconic cultural attractions such as the public Cloud Gate Sculpture.
Spacious Row Home Next Transit Near Downtown W Parking
- Picnic area/ Tables
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Garden area
Spacious Row Home Next Transit Near Downtown W Parking
Spacious Row Home Next Transit Near Downtown W Parking Chicago can host up to 16 guests, boasting a prime location 7 km from iconic cultural attractions such as the public Cloud Gate Sculpture.
Beautiful Remodeled Penthouse Unit In Old Town
- Cookware/ Kitchen utensils
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Heating
Beautiful Remodeled Penthouse Unit In Old Town Villa Chicago is nestled just a 5-minute walk from the Chicago History Museum and can accommodate up to 14 guests.
Beautiful Remodeled Penthouse Unit In Old Town
- Cookware/ Kitchen utensils
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Heating
Beautiful Remodeled Penthouse Unit In Old Town
Beautiful Remodeled Penthouse Unit In Old Town Villa Chicago is nestled just a 5-minute walk from the Chicago History Museum and can accommodate up to 14 guests.
Breathtaking Downtown Penthouse B - Sleeps 11
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Patio
Breathtaking Downtown Penthouse B - Sleeps 11 Villa Chicago provides easy access to various city attractions, such as the long-standing Carl Hammer Gallery, situated a mere 6 minutes' walk away.
Breathtaking Downtown Penthouse B - Sleeps 11
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Patio
Breathtaking Downtown Penthouse B - Sleeps 11
Breathtaking Downtown Penthouse B - Sleeps 11 Villa Chicago provides easy access to various city attractions, such as the long-standing Carl Hammer Gallery, situated a mere 6 minutes' walk away.
Personal Gym Luxury Balcony Condo
- Cookware/ Kitchen utensils
- Tea and coffee facilities
Located only a 5-minute walk from St. Joseph the Betrothed Ukranian Catholic Church, the spacious Near O'Hare • Personal Gym & Balcony • Safe Area Chicago apartment gives quick access to various tourist spots in the vicinity.
Personal Gym Luxury Balcony Condo
- Cookware/ Kitchen utensils
- Tea and coffee facilities
Personal Gym Luxury Balcony Condo
Located only a 5-minute walk from St. Joseph the Betrothed Ukranian Catholic Church, the spacious Near O'Hare • Personal Gym & Balcony • Safe Area Chicago apartment gives quick access to various tourist spots in the vicinity.
Spacious 5-Br House Near Transit W Parking
- Picnic area/ Tables
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Sun terrace
Up to 16 guests can stay at Spacious 5-Br House Near Transit W Parking Chicago villa and enjoy Blessed Sacrament Catholic Youth Center, located 6 minutes' walk away.
Spacious 5-Br House Near Transit W Parking
- Picnic area/ Tables
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Sun terrace
Spacious 5-Br House Near Transit W Parking
Up to 16 guests can stay at Spacious 5-Br House Near Transit W Parking Chicago villa and enjoy Blessed Sacrament Catholic Youth Center, located 6 minutes' walk away.
The Village Inn By Dakota Gal Digs
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Patio
Offering access to entertainment venues such as the half-mile-long Navy Pier, situated approximately 6 km away, the 3-bedroom The Village Inn By Dakota Gal Digs Chicago villa can host up to 8 guests.
The Village Inn By Dakota Gal Digs
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Patio
The Village Inn By Dakota Gal Digs
Offering access to entertainment venues such as the half-mile-long Navy Pier, situated approximately 6 km away, the 3-bedroom The Village Inn By Dakota Gal Digs Chicago villa can host up to 8 guests.
New Modern 3Br • Gym • Workspace • Quiet Location
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Laundry
- Fitness centre
Situated a 10-minute drive from the Harlem-Irving Plaza Shopping Center, New Modern 3Br • Gym • Workspace • Quiet Location Chicago apartment offers a Jacuzzi for 8 visitors. Wi-Fi is available for guests' business or leisure needs.
The presence of a fitness club will ensure guests' physical well-being.
New Modern 3Br • Gym • Workspace • Quiet Location
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Laundry
- Fitness centre
New Modern 3Br • Gym • Workspace • Quiet Location
Situated a 10-minute drive from the Harlem-Irving Plaza Shopping Center, New Modern 3Br • Gym • Workspace • Quiet Location Chicago apartment offers a Jacuzzi for 8 visitors. Wi-Fi is available for guests' business or leisure needs.
The presence of a fitness club will ensure guests' physical well-being.
Boutique Garden House Chicago 3-Story Sleeps 12
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Offering a location a 10-minute ride from the Sprawling hands-on Museum of Science and Industry, Boutique Garden House Chicago 3-Story Sleeps 12 Villa gives access to various tourist spots in the area.
Boutique Garden House Chicago 3-Story Sleeps 12
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Boutique Garden House Chicago 3-Story Sleeps 12
Offering a location a 10-minute ride from the Sprawling hands-on Museum of Science and Industry, Boutique Garden House Chicago 3-Story Sleeps 12 Villa gives access to various tourist spots in the area.
Perfect Location Across From Park & Train Station
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Garden area
Located only 450 metres from Midwest Athletic Club, the 5-bedroom Perfect Location Across From Park & Train Station Villa Chicago provides access to various tourist attractions in the vicinity. With a maximum capacity of 13 guests, the Chicago villa offers private parking.
Perfect Location Across From Park & Train Station
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Garden area
Perfect Location Across From Park & Train Station
Located only 450 metres from Midwest Athletic Club, the 5-bedroom Perfect Location Across From Park & Train Station Villa Chicago provides access to various tourist attractions in the vicinity. With a maximum capacity of 13 guests, the Chicago villa offers private parking.
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, $ | |
| The Avondale Guesthouse |
9.6 / 10 (129 Reviews) |
From 240$ | |
| Stunning Condo #2 - Downtown River North |
8.5 / 10 (34 Reviews) |
From 39$ | |
| Lincoln Park Living - 3 Queen Beds - Sleeps 6 |
8.7 / 10 (54 Reviews) |
From 112$ | |
| Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find |
9.8 / 10 (37 Reviews) |
From 270$ | |
| Lincoln Park Living - Suite 2 |
8.4 / 10 (22 Reviews) |
From 178$ |
More accommodations in Chicago
Frequently Asked Questions
Which luxury villas in Chicago are ideal for large groups?
The Stunning Duplex Condo #1 in Downtown River North and the Boutique Garden House Chicago offer spacious accommodations that can comfortably host large groups. They provide amenities like multiple bedrooms and living areas for easy entertaining.
Consider booking the Duplex for a stay in early June, as group rates might be more favorable before the summer tourism peak.
What luxury villas near downtown Chicago offer great views?
The Breathtaking Downtown Penthouse B provides stunning city views right from its rooms. Staying here allows quick access to the city's vibrant skyline and landmark spots.
Book your stay for a weekday to enjoy lower rates and fewer tourists at popular viewing spots like the Willis Tower Skydeck.
What luxury villas in Chicago have a private patio or balcony?
The Designer Themed 4 Bedroom in Best Location features a lovely patio, perfect for weekday breakfasts, while the Personal Gym Luxury Balcony Condo also offers stunning outdoor views.
Choose the balcony suite for evenings, as sunset views over the city can be quite magnificent.
Which luxury villas in Chicago are pet-friendly?
The Northside Famlynest Lincoln Sq welcomes pets, ensuring your furry friends can join you on your trip. Spacious settings make it easy for everyone to feel at home.
Contact the villa ahead to confirm specific pet policies and to find nearby parks for walks, like Welles Park.
Are there luxury villas in Chicago with spa facilities?
Many luxury options, including some high-end hotels nearby, offer spa services. For a true luxury experience, check out spa treatments available at venues like The Spa at Four Seasons.
Book your spa appointments in advance for summer weekends, as they tend to fill up quickly.
What luxury villas in Chicago provide family-friendly amenities?
The Boutique Garden House offers amenities suitable for both adults and children, making it a good option for families. Spacious common areas accommodate everyone comfortably.
Consider visiting during the off-peak season for family-centered events in neighborhoods like Lincoln Park.
Which luxury villas near Chicago landmarks are best for sightseeing?
Stay at the Stunning Condo #2 in Downtown River North for walking distance to the Art Institute of Chicago and Millennium Park. This location enables you to explore easily.
Plan to visit Millennium Park early in the morning to enjoy art installations like the Cloud Gate before crowds arrive.
What events should I plan to see in Chicago throughout the year?
Chicago hosts many notable events, including Lollapalooza in late July, the Chicago Air and Water Show in August, and the Chicago Christmas Market in December. Each offers a unique experience and vibrant atmosphere.
Book accommodations early in February to secure the best rates, especially during Lollapalooza when demand is high.
What is the best way to get around Chicago's downtown area?
Using the Chicago Transit Authority (CTA) trains and buses is often the most efficient way to get around downtown. The Red Line connects many key areas including the Magnificent Mile and the Loop.
Purchase a Ventra card for unlimited rides, as it's more cost-effective than paying cash per trip.
Which areas in Chicago are safe for walking at night?
Districts like River North, Lincoln Park, and the Loop are known for being safe after dark, with plenty of nightlife and dining options. Staying in these neighborhoods helps ensure a secure environment.
Stick to well-lit streets and main thoroughfares when exploring at night, avoiding isolated alleyways.
Chicago and related destinations