We have two really incredible vacation rental apartments.
We are offering great special off season rates for our Winter Months through March. These specials range from $110 per night to $195 per night and as low as $875 per week.. The best rates are for longer rentals and some dates will have a minimum stay. We also have the December Holidays available at discounted rates.
We lived in this building ourselves for many years and have now offered them as vacation rentals for 7 years. We lived in this building for 9 years and in this neighborhood for 19 years. We completely renovated our building with many great amenities that you won't find in many rentals.
We are experienced owners and have never had more than a minor complaint. We have around 200 guest comments from previous guests at the many sites that we have ads at. We are proud to say that all of our reviews gave us 4 or 5 stars. Please see our reviews in this ad and we will send you a few more when you send an inquiry.
The view in our first picture is our 5 star hot tub. It's your new best friend after a day of travel, sightseeing, or business. The next photo is the Chicago City Skyline view from our deck (closed for most of winter). They are both great places to relax.
If this apartment isn't available, here is the link to our ad for our other apartment, http://www.flipkey.com/chicago-condo-rentals/p291255/
This apartment has 3 bedrooms and each has a queen bed. It sleeps a maximum of 6 people. We also have a queen air bed that can be set up for one extra sleeping space.
We are close to all of the sights of Chicago and our convention center, McCormick Place. The I-94 expressway is 1/4 mile away. We have a bus 1/2 block from our door and the train is a short walk. It is easy to get anywhere in the city from our door.
It is a 10-15 minute drive or cab ride or it's a quick train ride to all of our great attractions on our great public transportation system. Ours is a safe and quiet neighborhood. 5 of our last 8 Mayors grew up in this neighborhood.
Some of the amenities that our guests really love are our deck with a breathtaking view of our amazing city skyline, our 6 person Luxury Hot Tub and our huge 3.5 x 5 shower with Grohe body sprays and steam bath generator. Please see these in our pictures section.
Our rentals are located just South of Downtown Chicago. We are 2.5 miles SW from McCormick place and 5 miles due south from Grant Park and our major attractions.
If you are coming for a conference at McCormick Place, please let us know when you inquire and we'll send travel information.
PLEASE CHECK OUR UPDATED AVAILABILITY CALENDAR BEFORE INQUIRING. We have two comfortable apartments with many luxurious features that our guests enjoy. We have over 100 guest comments between all of our other online ads from 5 years of offering rentals.
Each apartment has one full bathroom with the luxurious shower as shown in our photo section. There is an additional half bath that is shared that is located in our basement that both apartments use as a backup.
We are located on a quiet and peaceful block. Our daily newspaper, the Chicago Sun Times recently reported that our neighborhood was voted the best place to trick or treat based on the safety and the family atmosphere of our area. This is what they had to say.
The best neighborhood for trick-or-treating in Chicago? Bridgeport, says Zillow. They factored in where a kid's likely to get 'the most candy, with the least walking and minimal safety risks.' Bridgeport gets props from Zillow dot com as 'really a family neighborhood.
If you'd like to see a larger map and search nearby attractions, please google 529 W 37th Street Chicago IL 60609 to see a larger map. At Google Maps, you can then click on 'search nearby' or 'get directions' to see our location in relation to the attractions that you'll be traveling to during your stay. We are very close to everything people come to Chicago for.
Our area is safe and close to our city center and McCormick Place. That has made it a very high demand residential destination for years now. One of our neighbors built a large mansion on 5 lots and next door is a huge house with an indoor swimming pool that is on the market for $1.7 million. New construction and completely renovated buildings like ours are the norm.
We have fully stocked modern kitchens. We include one garage parking space with your rental.
AN IMPORTANT NEW DEVELOPMENT CONCERNING VACATION RENTALS IN CHICAGO.
The City of Chicago has a new local ordinance that regulates vacation rentals. We are a legal vacation rental and our license number is 2074659. Enforcement of this Ordinance has begun. Unlicensed properties can be shut down by the city and/or their condo association at any time. For these and other reasons, we recommend that you book your rental with a licensed Vacation Rental Owner.
Our cleaning costs $100 per stay
Damage Deposit $200 per stay
This site's quotable rates are not very accurate for how we price our rentals. Our per night rates are lower for longer rentals and we always have a range of rates. There is no one nightly or weekly rate. Our rates depend on the season, the length, and timing of your stay. Our 5 or 7 night rates are a better per night rate than 3 or 4 nights.
We have a 3 or 4 night minimum or more at all times although we will offer 3 or sometimes 2 night rentals at the last minute when we have a higher minimum. Our rates vary from $120 to $240 per night and $775 to $1,575 per week. Our rates always depend on the timing and length of your stay.
Our best rates are for longer stays. Shorter stays are priced higher due to fixed costs. Rates for Winter are our lowest guest rates and rates for Summer, major holidays and special events are our high season rates.
We don't allow parties or gatherings of any kind. Our rentals are not a good fit for the very late night or very hard partying crowd. We require the guest renting the apartment to be an adults of 25 years of age or older. Our guests appreciate that we have a quiet and peaceful environment.
The maximum capacity of the apartment is 6 people in 3 queen beds (and an air bed that can be set up for one extra sleeping space). We will sometimes make slight adjustments on these limits with prior approval.
Our personal cancellation policies vary from what is listed on this site. This site is not set up to display our very customized policies. This site's policies regarding cancellation fees and deposits will apply if you book your rental through this site. If you reserve your rental through us, our deposits are less and our personal cancellation policies are more forgiving. Our policy is a $100 cancellation fee if canceled 45 days or more from the rental and a $250 cancellation fee if canceled between 45 and 30 days from the rental. This policy is adjusted for rentals that are longer than 7 nights and for some special events. If there is a cancellation less than 30 days from the rental (or in the case of early departure during your rental), refunds are only made if we can re-rent the dates to someone else. Then we would refund whatever we get for as many of those dates as we can re-rent at normal or last minute rates, minus the applicable cancellation fee....Read more
HUGE WINTER DISCOUNTS. GREAT REVIEWS 1 FL. HOT TUB Chicago, Illinois
Additional Location Information
Ours is a safe and quiet neighborhood that is very close to downtown Chicago. You can get anywhere in our city center in 10-15 minutes in a car or cab and public transportation is great if you want to take the train. Our convention center, McCormick Place is 2.5 miles away and is less than a 10 minute drive.
To see a better map of our location, please enter 529 W. 37th Street, Chicago, IL. 60609 into Google maps or any mapping site. Please zoom the map out a few levels and scroll north and you can see our location in relation to all of our great attractions. In google maps, you can click "search nearby" or "get directions" to enter in locations that you will be traveling to during your stay.
More About This Location
Nearest airport: Midway Airport, 7 miles Nearest train station: Amtrak, 3 miles Car is not necessary
Last updated on February 24, 2015
Not available for your dates? Check availability for 222 other Chicago rentals
Left on 10/08/2013 for a stay in October 2013 | Kev
The apartment is easily accessible, clean, large, well furnished and very well equipped. Bob rent this apartment as if he would live there which makes you feel at home. The kitchen is very well equipped with utensils, large fridge, 4 burner gas, utensils for the barbecue (out in the garden) there are even spices!
The spa is very nice.
The presence of washing machine and dryer are also very appreciable and also they have a very large capacity! The beds are very comfortable.
In addition, the access code makes very easy to arrive and also during the stay.
Left on 10/20/2012 for a stay in October 2012 | Marta
This cozy nest was a blessing. Bob's suggestions were ideal and the location was perfection. We enjoyed Chicago and we enjoyed coming home to our nest. The downside was that we didn't have more time to visit this wonderful place.
Left on 04/18/2012 for a stay in March 2012 | A FlipKey verified reviewer
This was a great apartment and it had everything we would need as a family. Very quiet neighbourhood..Beds were comfortable, fully serviced kitchen and very clean. Bob was very easy to deal with and we appreciated his help. The only downside we did have was that the grocery store was a fair walk (we weren't quite sure where the closest one was and did not have a car)so we were limited with what we could buy/carry home. Perhaps some directions to the grocery store would have been useful in the information but I am sure that had we have rung the owner he would have been more than happy to advise us. 10 minute walk to Red line train. Was a little out of the city area but the apartment made up for it. Thanks again and would certainly highly recommend.
Left on 03/15/2012 for a stay in March 2012 | A FlipKey verified reviewer
Renting from Bob...wonderful communication. The property shown on the video and described exactly to a tee!
The condo was perfectly clean and had all the accouterments you need.
We would definitely stay again!!
Left on 02/29/2012 for a stay in February 2012 | Gina
This was a great rental for our family. It was much more comfortable than a hotel. It was clean and had modern appliances and a really nice shower. The garage was convenient and we appreciated the little extra supplies. The neighborhood was quiet, and we felt quite safe. I would highly recommend it.
Left on 10/13/2011 for a stay in October 2011 | A FlipKey verified reviewer
My husband and I stayed for a week in October.We arrived after a very long trip from australia and we were very tired. We found the apartment to be very clean and had everything we needed. The apartment had great amenities and very comfortable beds! The bathroom was great as was the kitchen. The apartment was close to transport and we found it easy to get around. Would stay there again.
Left on 08/10/2011 for a stay in July 2011 | Brian G.
I have many great things to say about our stay, but I hate to ramble so I'll make it simple:
- The location was wonderful. Quiet neighborhood, friendly neighbors, easy walk to the ballpark and 15 minute subway ride to downtown.
- The condo is incredible. The beds are comfortable, the kitchen and living room are spacious, the washer and dryer saved us (it was hot outside and we had to change several times a day) the hot tub is transcendent and the roof deck is the icing on the cake.
- The owners are very accommodating, easy to deal with and in general seem to be reasonable people.
I'll never stay in a hotel again for an extended trip; this stay has completely sold me on condo rentals for vacationing, although I imagine it'd be tough to find a more ideal spot.
Thank you for your nice thoughts Brian. We're so glad that you had a great time. It was a brutal heat wave when you here. We're all glad that seems to be over. It was so hot that I'm surprised you could enjoy the hot tub. Bob
Great place, convient to conference center
Left on 05/18/2011 for a stay in May 2011 | trisler
The owner was extremely helpful. The place was great. Very clean and larger than the pic make it out to be. Just a short drive to the McCormick Center.
Fantastic, comfortable stay. Better than any hotel!
Left on 03/21/2011 for a stay in March 2011 | NBloom
I traveled in a group of 6 female hair stylists. This apartment was perfect for us. Two of the three bedrooms had large mirrors(which were much needed) getting 6 hair stylists ready in the morning was a breeze. The beds were cozy, and the sheets and comforters were good quality.
The hot tub, roof deck and garage were amazing bonuses. The view of the downtown skyline from the roof deck is gorgeous. The full kitchen helped us save so much money, we made one big meal each day we were there.
Definitely check out Kathy De's deli around the corner. The owner is a great man, he was so nice and helpful to us during our stay.
We were in Chicago for the Hair Show, which was at McCormick Place. The cab ride to McCormick was quick and affordable. Getting to Downtown was a different story of course, but we knew that and weighed our options before hand. I wish we would have been there during baseball season! The proximity to the stadium is unbeatable. Read more
Thank you for the very nice comments Nichole. We're happy to hear that you and your group had a great time. It sounds like you had trouble getting downtown and I'm really surprised to hear that. The red line train station at 35th street is 1/2 mile east of us and runs every 10-12 minutes 24/7. It's 2-4 train stops to the museums, downtown or Millenium Park. It's no different getting downtown from our near south side location than from the north side neighborhoods of Lincoln Park, or Wrigleyville as . It's the same red line train. What I loved about our location when I moved from that area is that there is less traffic from our side of town if you are driving. When I drive, I get anywhere downtown or on the near north side in 15-20 minutes with light or medium traffic. That's a lot harder to do from the north side where traffic can be heavy, especially on weekends, or even more so in summer. Thanks again, Bob
A Christmas to Remember
Left on 01/03/2011 for a stay in December 2010 | Trisha Lee
We had a brilliant Christmas in this appartment. Everything was as described, lots of information provided on places to go, things to do and how everything worked. Our flight was delayed by one day and Bob kindly let us make this up with a day the other side. The roof garden was amazing and i will take with me the memory of standing up there in the snow on christmas eve, whilst the bells in the neighbouring church played christmas carols and snow fell down on us. Certainly a Christmas to remember.
Left on 12/06/2010 for a stay in November 2010 | leparris
5 of us stayed in the 2nd floor apartment and a great stay. There is plenty of room to spread out so we never felt like we were on top of each other. The place is very clean and has every amenity you could wish for. The location is very close to the bus stop and we even walked to the L station a couple of times. If I ever get a chance to go back to Chicago, I will definitely stay here again.
Left on 09/24/2010 for a stay in September 2010 | Wx3Guy
If you are planning a trip to Chicago for some of the sights, this is the place to say. The location is about perfect as the longest drive we had to any of the museums was about 15 minutes. We would have walked and caught a Sox game, but because of the rain we opted to do something else indoors.
The apartment was clean and had everything that we needed. The shower in the bathroom was just awesome. We also personally got a bit of enjoyment with the toaster. (Stay here and use the toaster to find out!) It was also very nice to have a garage to park in. We also enjoyed the opportunity to sit on the roof deck and check out the city scape.
The only minor concern we had was that the 2nd bathroom is shared between the two apartments. We never had to use it and would have worked if needed.
In short, this place comfortably fit the 4 of us on a Chicago trip and provided a good place to crash at night. We highly recommend it. Read more
Left on 09/15/2010 for a stay in September 2010 | Ken
Comfortable and very clean apartment in a nice neighborhood. Amenities are nice: large-screen TV, free computer, ultra-modern bathroom, well equipped kitchen. We enjoyed cocktails on the roof deck with a view of the skyline and the hot tub was a hit with our runners in the half-marathon. Bob provides an amazing amount of information to you on local restaurants, getting around, etc.
Only concern was very little within walking distance and local buses proved unreliable off-hours. Street parking is plentiful and there is a 2-car garage, so next time we will rent a car. Definitely will rent again when we return to Chicago. Read more
Most people take the train into the city. It runs every 8-10 minutes 24-7 and never has problems with traffic. For those who can't or don't want to walk the 1/2 mile to the train, the bus 1/2 block away is an easy option.
Buses usually run every 10-15 minutes and most of the time they do. I remember that you saw 3 or 4 buses going the other direction while you were waiting, so that certainly was a factor. Our transit system is pretty good, but very far from perfect.
Thanks again for the nice comments. Bob
Very Satisfied Renter
Perfect home away from home
Left on 09/08/2010 for a stay in September 2010 | Very Satisfied Renter
What a great alternative to a hotel/motel. I almost felt guilty for not spending more time enjoying all the well thought out amenities that are tucked into this spacious apartment. For us, being situated in a quiet neighborhood on the outskirts of the city (with a garage!) was perfect. We will definitely be contacting Bob our next trip back to Chicago. Thanks - thoroughly enjoyed our stay. Read more
Thank you Deb. We're glad that you enjoyed our Labor Day vacation with us. We are only 4.5 miles from downtown Chicago, not quite on the outskirts of the city. We get downtown in less than 10 minutes when it isn't rush hour. Bob
A great place to relax, unwind & enjoy Chicago
Left on 08/05/2010 for a stay in July 2010 | Terry O
What a wonderful "South Chicago" apartment style rental. I traveled with my wife, three kids/yound adults (ages 19 to 22) and we all truly enjoyed ourselves. The apartment is roomy and accommodating with several nice amenities, including a big jacuzzi and relaxing spa shower. The neighborhood location is charming and friendly, offering local and cheaper dining options. The location has easy access to downtown Chicago and the added bonus of parking. We were all so much more comfortable than had we stayed in a hotel. There are many great features about this rental that make it easy to relax and unwind. This is the only place we will consider on our next trip to the great city of Chicago. We were already missing it on our way home!!
Left on 07/20/2010 for a stay in July 2010 | A FlipKey verified reviewer
Fantastic apartment! Working with Bob was easy. We traveled with our 4 kids, 8-16 years old. The apartment was spacious, well-kept, well-furnished. Hot tub was large, very clean, very relaxing. Lots of stores nearby, easy to get to Lakeshore Drive. The immediate neighborhood was nice. Bob left resource books with great info on local restaurants, busing, safety tips.
Left on 07/20/2010 for a stay in July 2010 | drdwilcox
This is a great apartment. The rooms are comfortable, the facilities are great (laundry, garage, full kitchen, dishwasher), and they include a reasonable amount of cleaning in the rental price - this has never been my experience. The nearby restaurant has great food and great people. Public transit is really close. We loved staying.
Left on 04/07/2010 for a stay in April 2010 | Lisa
My family of four (parents plus two pre-teen daughters) stayed at Bob's place for a week during spring break. We were able to enjoy the comfort and privacy of a home that provides luxury amenities and do all the sightseeing (museums, zoos, aquarium, Sky Deck, Navy Pier, Blue Man Group) we wanted without breaking the bank - and we still had an extra bedroom! The things we enjoyed most about Bob's place: 1) hot tub, 2) rooftop deck, 3) luxury shower, 4) well equipped kitchen, 5) local neighborhood restaurants (we recommend Kathy's for breakfast sandwiches and Rico Bene's for delivery Italian & great Chicago hotdogs!), 6) convenience of location to highway and downtown (we could get everywhere we wanted to go in 10-20 mins), 7) garage parking. When you stay at Bob's place, he provides you with a ton of very thorough pre-trip information and tips that will help you get the most out of your experience while being cost conscious.
Would you recommend this vacation rental to a friend?
Recommended for: Friends, Groups, Tourists, Families w teenagers, Families w children, Rugged, Romantic, Singles, Luxury, Disabilities
Best deal near downtown
Left on 12/18/2009 for a stay in December 2009 | Andre
The great news with Bob's home is that there are no bad surprises. It is everything the add says. What doesn't come out of his add is that it is very spacious. Bob is very forthcoming with a very useful housebook to get around the neighbourhood and downtown, even better he is only a phone call away and he does answer his phone.
Would you recommend this vacation rental to a friend?
Recommended for: Friends, Tourists, Families w teenagers, Families w children, Rugged, Singles
A FlipKey verified reviewer
Incredible Place to Stay!!
Left on 12/08/2009 for a stay in December 2009 | A FlipKey verified reviewer
Bob was great from the first phone call to inquiry about our stay. The apartment was amazing from the cleanliness to the steam shower(amazing). The location was very convenient to get downtown or just enjoy the neighborhood pubs. I will definitely be back in the summer for a baseball game. Thanks a lot Bob.
Home Away From Home!
Left on 11/12/2009 for a stay in November 2009 | Debbie
This place was amazing! It was very welcoming and stocked with everything you might possibly need on your trip and then some; from shampoo, body wash, q-tips, hair dryer, iron….all the way to coffee and condiments, it was all there. It was also nice to have internet access. The hot tub was really clean and relaxing. The beds were very comfortable and the shower was heavenly. It had 5 shower heads and steam (if you wanted). There was also a towel warmer!
There was a marvelous view of the city from the rooftop deck. The location was great and the neighborhood was very safe. There is also little store/sub shop located around the corner which was convenient if we just wanted to grab a quick bite to eat. Having a garage to park a car in was nice as well. It is a great value for the money.
Not only was it a great value for just the stay itself but the owner, Bob, was fantastic. He was very helpful and excellent at answering all of our questions before and after we arrived in Chicago. He always answered his phone, day or night, and it made traveling around Chicago much easier. He also sent us information before we arrived on everything we wanted to know such as: public transportation, local shopping, dining, and activities.
Would you recommend this vacation rental to a friend?
Recommended for: Friends, Groups, Tourists, Families w teenagers, Rugged, Families w children, Singles, Luxury
A FlipKey verified reviewer
Best place in Chi-town
Left on 10/25/2009 for a stay in October 2009 | A FlipKey verified reviewer
This is a great unique place to stay if you are in Chicago and want something other than a boring hotel. It is a quick trip downtown via train or cab. PLENTY of room for a family. VERY comfortable. Full sized kitchen with everything you need to cook a full meal. PLUS a great rooftop deck and a hot-tub down below. A stones throw away from the White Sox. I think this would be especially great if you travel a lot and are already familiar with the layout of the city. Nothing less than a home away from home. The owners are very helpful and accommodating and are more than willing to fill the role of concierge. I'll be back next time I'm in town! Read more
Thank you Rob. It is always a pleasure to have such nice people stay with us, We look forward to seeing you again when your travels bring you back to Chicago.
A FlipKey verified reviewer
Best value for money for staying in Chicago
Left on 10/14/2009 for a stay in October 2009 | A FlipKey verified reviewer
Bob C is a fine man, he provided everything we needded in our stay in his apartment, the apartment is very confortable and if you have a car the parking is not a problem at all. The train to the city center in only 8 blocks away which makes visiting downtown very easy and cheap. Read more
Thank you Tania. You were definitely one of the nicest people that we've had stay with us. You were so clean that we could barely tell that anyone had been there. I can't tell you how much we appreciate that. The CTA Red Line station at 35th street is a short 1/2 a mile east of us. That is also where the expressway is for those who will have a car. We also have a bus that is 1/2 block away that can take you directly to the Orange line train that runs between Midway Airport and downtown. They both run every 8-10 minutes. Thanks again, Bob
As featured in USA TODAY and recommended by Travel + Leisure in its annual Villa Guide:
New to FlipKey?
FlipKey is a vacation rental marketplace with more than 300,000 rentals around the world. Find the perfect place to stay for your trip, and get great value along with the space, privacy and amenities of home.
Find the vacation rental perfect for you. Learn how.