Chicago Luxury Vacation Rentals, Apartments, & More - 551 Rentals Available

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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 / 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 / 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 / 10

Chicago Apartment
1 BR / 1 BA / Sleeps 3 1 3 No min stay
Apartment / 1 Bedroom / Sleeps 3
1 bedrooms 1 bathroom Sleeps 3
High Speed Internet • Dishwasher • Microwave
"The apartment was very nice with ano impressive view of Millennium park. It's near shops and well- known attractions. Communication was excellent and all was set in no time."
- Veronica guala, Chicago, Illinois USA
(10) Excellent (10 reviews)
1 / 6

Chicago Apartment
1 BR / 1 BA / Sleeps 3 1 3 No min stay
Apartment / 1 Bedroom / Sleeps 3
1 bedrooms 1 bathroom Sleeps 3
High Speed Internet • Dishwasher • Microwave
"I M student in UIC and I have stayed there for a week and I found this place is very nice, clean and nearest from many restaurant and trains also the furniture is very simple and convenient to us"
- Hanadi Mardah, Chicago, il USA
(6) Excellent (6 reviews)
1 / 7

Chicago Condo
2 BR / 2 BA / Sleeps 4 2 4 Min stay varies
Condo / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
Dishwasher • Microwave • Air Conditioning
"We stayed for 2 weeks. The location is the best of possibles: food market, beach, parks, transportation, most of remarkable places are nearby in a walking distance. Apartment is on the 42nd floor, swimming pool with open air- on 56th. We were wondered..."
- Tanya Miller, Boston, MA
(14) Excellent (14 reviews)
1 / 37

Chicago Condo
2 BR / 2 BA / Sleeps 6 2 6 No min stay
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"We spent a week here at the end of September. The apartment is perfectly located for shopping and restaurants on the magnificent mile and for the museums. The building is eclectic and the interior stylish. . The unit is extremely well equipped and the..."
- Steve Hutchison, Crickhowell, UK
(27) Excellent (27 reviews)
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 / 11

Chicago Apartment
3 BR / 2.5 BA / Sleeps 8 3 8 No min stay
Apartment / 3 Bedrooms / Sleeps 8
3 bedrooms 2.5 bathrooms Sleeps 8
"We were a group of 7 women sharing this 3 bedroom/3bath condo. Absolutely beautiful! ! Very clean with incredible views. Having a square table easily sat all of us (could have had a couple more chairs) as we chatted over wine. The only complaint we..."
- Carolyn Black, Colorado Springs, CO
(44) Excellent (44 reviews)
1 / 16

Chicago Condo
3 BR / 2 BA / Sleeps 6 3 6 3 night min stay
Condo / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"The condo was beautiful the view was amazing. A very secure building I would highly recommend it."
- Paula Grandfield, Hamden ct
(1) Excellent (1 review)
1 / 7

Chicago Condo
3 BR / 2 BA / Sleeps 6 3 6 3 night min stay
Condo / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"We rented this condo in August. First of all, the location is perfect, right in the middle of everything. But the highlight of this place is the view on Grant Park and Millenium Park. One of the best view of Chicago. As for the condo itself, it was..."
- Marie-josé Raymond, Montréal, Canada
(8) Excellent (8 reviews)
1 / 9

Chicago Apartment
2 BR / 2 BA / Sleeps 5 2 5 3 night min stay
Apartment / 2 Bedrooms / Sleeps 5
2 bedrooms 2 bathrooms Sleeps 5
High Speed Internet • Dishwasher • Microwave
"I traveled to Chicago for a long business trip and chose to stay in a condo instead of a hotel. One Superior was the perfect place and location. Everything was within walking distance, great views, 7th Floor access to gym, pool, library were awesome!"
- christine grossmith, Carlsbad, CA
(4) Excellent (4 reviews)
1 / 15

Chicago Apartment
Studio / 1 BA / Sleeps 2 0 2 3 night min stay
Apartment / Studio / Sleeps 2
Studio 1 bathroom Sleeps 2
High Speed Internet • Microwave • Air Conditioning
"As a turist and our first time in Chicago after many hours of walking and seen the City, was so great to arrived at the suite with the guaranty that we could relax and refresh because we hoy a prívate place and non noisy. The suite is near of everything..."
- Claudia Abaunza, México city
(1) Excellent (1 review)
1 / 24

Chicago Home
3 BR / 3 BA / Sleeps 7 3 7 4 night min stay
Home / 3 Bedrooms / Sleeps 7
3 bedrooms 3 bathrooms Sleeps 7
High Speed Internet • Dishwasher • Microwave
"We just returned from a fabulous stay in this beautiful home. The house was very clean, spacious, nicely decorated and in a great neighborhood that is walkable to many shops and restaurants in the hip area of Bucktown. We really enjoyed the gourmet ..."
- Robyn Barnett DeRosa, Columbus, OH
(2) Excellent (2 reviews)
1 / 38

Chicago Apartment
2 BR / 1 BA / Sleeps 6 2 6 3 night min stay
Apartment / 2 Bedrooms / Sleeps 6
2 bedrooms 1 bathroom Sleeps 6
High Speed Internet • Dishwasher • Microwave
"We did not stay at this property as there had been a fire which had left damage. The owner's sister let us stay at her property literally across the same road. Or we were offered a full refund. All dealings with the family were professional and courteous,..."
- Sandra Tuttle, NYC
(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)
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)
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