Chicago 4+ bedroom Vacation Rentals, Apartments, & More - 486 Rentals Available

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1 / 17

Chicago Home
4 BR / 3.5 BA / Sleeps 24 4 24 Min stay varies
Home / 4 Bedrooms / Sleeps 24
4 bedrooms 3.5 bathrooms Sleeps 24
High Speed Internet • Dishwasher • Microwave
"We actually booked the house to shoot some industrial video, and were very pleased to find that no 'trick photography' had gone into the website photos (unlike some of the other locations we used in the series! ), and we had plenty of room to maneuver,..."
- K Woolf, Rogers Park, Chicago, IL
(10) Excellent (10 reviews)
1 / 8

Chicago Apartment
4 BR / 2 BA / Sleeps 8 4 8 3 night min stay
Apartment / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"Fran's Bella Apartment was one of the most gorgeous accommodations I have ever lived in. It was majestic from every perspective right from the looks , the feel and the ambiance. The house has a wonderful aura to it and I felt very cozy living in it. ..."
- Sayida Bano, woodstock , IL
(12) Excellent (12 reviews)
1 / 6

Chicago Condo
4 BR / 2 BA / Sleeps 10 4 10 Min stay varies
Condo / 4 Bedrooms / Sleeps 10
4 bedrooms 2 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
"awesome location, very clean, updated unit, very reasonable, we had a great time, no problems whatsoever, we will rent again, allot cheaper than a hotel ."
- Sandra Eagen, wyomint, ontario, canada
(2) Excellent (2 reviews)
1 / 39

Chicago Guesthouse
5 BR / 2 BA / Sleeps 9 5 9 3 night min stay
Guesthouse / 5 Bedrooms / Sleeps 9
5 bedrooms 2 bathrooms Sleeps 9
High Speed Internet • Dishwasher • Microwave
"We ended up staying at a smaller property owned by Teri due to the size of our group. It was delightful! Teri provided everything including Christmas decorations! She is the perfect hostess and the properties are exactly as described and better. ..."
- Pamela Winch-Matayoshi, SanDiego,CA
(3) Excellent (3 reviews)
1 / 25

Chicago Home
7 BR / 2.5 BA / Sleeps 20 7 20 Min stay varies
Home / 7 Bedrooms / Sleeps 20
7 bedrooms 2.5 bathrooms Sleeps 20
High Speed Internet • Dishwasher • Microwave
"I cannot say enough about this experience. We had rented another property for a party for my daughter's 18th birthday which turned out to be a scam. I had been in contact with Anna about this property, but the other was cheaper and met our needs. When..."
- Kathryn Murray Kzeski, Chicago, IL USA
(4) Excellent (4 reviews)
1 / 30

Chicago Condo
6 BR / 2 BA / Sleeps 16 6 16 3 night min stay
Condo / 6 Bedrooms / Sleeps 16
6 bedrooms 2 bathrooms Sleeps 16
High Speed Internet • Dishwasher • Microwave
"Great place, exactly as pictured. Our stay was enjoyable and hassle free. Owner was easily reached via email/text if needed."
- Courtney Armstrong, Milwaukee, WI
(4) Excellent (4 reviews)
1 / 37

Chicago Apartment
4 BR / 2 BA / Sleeps 8 4 8 3 night min stay
Apartment / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"Great place to stay. Close to the train, lots of great restaurants, all within close walking distance. It also had available street parking for our car. The owner meet us when we arrived and answered all of our questions. He also gave us ..."
- Randy Waskowiak, Nebraska
(1) Excellent (1 review)
1 / 30

Chicago Condo
4 BR / 4 BA / Sleeps 14 4 14 3 night min stay
Condo / 4 Bedrooms / Sleeps 14
4 bedrooms 4 bathrooms Sleeps 14
Dishwasher • Microwave • Air Conditioning
"We stayed here for two nights to catch up with good old friends. Exactly as described online. Everything went as planned and security deposit was refunded promptly after departure. For a group of 9, the house was perfect offering, many sleeping areas..."
- Sina Haghani, Ann Arbor, MI
(2) Excellent (2 reviews)
1 / 13

Chicago Home
5 BR / 3 BA / Sleeps 12 5 12 No min stay
Home / 5 Bedrooms / Sleeps 12
5 bedrooms 3 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
"I needed a place for 7 in my family to stay somewhat near Rogers Park in Chicago. This apartment was a perfect fit for us - a beautiful apartment in a beautiful neighborhood. The owner was very gracious and accessible for the few questions we had. It..."
- Mary Russell Clark, New Hampshire
(12) Excellent (12 reviews)
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