Close to Downtown & McCormick Place. Amazing View.

Our Luxurious 6 Person Hot Tub
Our Luxurious 6 Person Hot TubChicago Skyline View from our DeckLiving Room View #2Our 5 ft x 3.5 Foot Walk in ShowerClose up of our shower spraysDining RoomBedroom #1Bedroom #2Kitchen View #1Kitchen View #2Jennifer Sleeper Sofa with Memory Foam TopperBedroom #2 Closet
4 Reviews

From $179 / night

529 W 37th St, Chicago, IL 60609
Close to Downtown & McCormick Place. Amazing View.
2 bedrooms
6 guests
Varies min stay

Overview Description


Bedrooms: 2
Bathrooms: 1.5
Sleeps: 6
Type: Apartment
Per night: $180 - $245
Per week: $1,250 - $1,650
Pets allowed: No
Internet: Yes
Description of the Chicago vacation apartment rental
Close to Downtown & McCormick Place. 15 min by car or cab or 2-3 train stops from everything that Chicago has to offer.

Here are our winter specials. We sometimes run a separate specials ad

We are offering huge Discounts for our Winter months. 7 night rentals are $875 or $125 per night. 6 night rentals are $825, 5 night rentals are $750 and 4 nights are $675. 3 night rentals are $180 to $210 per night. Holidays and some special events will have different pricing. Longer term and very last minute rentals are available at further discounts.

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 in winter). They are both great places to relax.

This apartment has 2 bedrooms and 3 queen beds. The 3rd queen bed is a Jennifer Brand sleeper sofa with a memory foam top that is in our huge living/entertainment room. Our living room is at the far end of the apartment and is very private for anyone sleeping there. We also have a queen air bed that can be set up for one extra sleeping space. This apartment sleeps a maximum of 6 people.

It is a very fast trip to downtown, the museums and all of the great attractions of Chicago from our door.

We also have a second apartment in this building that has many more guest reviews. That listing # is 31547 and there is a link in this ad. If this apartment is booked for your dates, or if you have a larger group and would like to rent both apartments, you can rent our entire building if they are both available.

We have a bus 1/2 city block from our door to the orange line train stop and McCormick Place or the red line train is a 1/2 mile walk away. Both trains can get you anywhere in the city.

We have two comfortable and convenient apartments with many luxurious features that our guests love. We are fortunate enough to have many past guests who agree. Please see our many happy guest reviews and additional photos below the main photo. We do offer last minute specials in the last 2-5 weeks.

We always have a range of rates. There is never just one rate. Please inquire with your dates and we will respond with our best rate quote for your stay.

We have a 4 night minimum in summer and a 3 night minimum most of the rest of the year. We'll sometimes only book 3 night rentals in the last 2 months before the dates in question as we prefer longer rentals. We have a one week minimum for July 4th and the December holidays

We offer shorter rentals than our minimum at the last minute or if that is what we have available between other rentals. Shorter rentals are usually priced higher to cover our fixed cleaning and paperwork costs unless we offer a last minute special.

Our summer rates vary from $220 to $275 per night. Those rates include lodging tax of 16.4% and our cleaning costs. Your guest rate will depend on the length and timing of your stay.

PLEASE check the availability calendar for the dates of our stay before you contact me. We do keep it updated and it will save both of us time.

Our daily rates vary from $140-$270 per night and the weekly rates vary from $950-$1,700 depending on the season, the length of your stay, and other variables.

We also offer winter special rates in January, February, and the first half of December that can go as low as $100 per night for longer term rentals. All rentals require local lodging taxes and our cleaning costs.

Please email us with your travel dates and we'll respond with our best possible guest rate for your stay.

The luxury features of the rental include: 6 person Luxury Hot Tub, Incredible Chicago skyline view from our Roof Deck, Huge Walk in Shower with Grohe Body Sprays and Steam Bath Generator.

Each apartment has one full bathroom with the luxurious shower as shown in our photo section. There is an additional half bath in our basement that is shared by both apartments as a backup.

The other basic amenities are: Wireless High speed internet and a desktop PC for your use. Queen Beds. Original Pine Hardwood Floors. Cedar closets. Weber Stainless Gas Grill. There is one full bathroom in the apartment. You can see the picture of our luxurious shower in this ad. Our half bathroom is located in our basement and is shared between both apartments.

The apartment is also stocked with many of the basic necessities that you will need during your stay such as coffee, tea, soap, paper products, laundry soap, etc. I rent myself 2-3 times a year. There is nothing I hate more than having to run right out to a store for something that should be in the rental.

We are located just south of downtown Chicago. You can view a better map of our location at Goo gle Maps by typing in the following information.

529 W. 37th Street Chicago IL 60609. This is not our address, but it is very close. Scam artists steal details like these and create their own online ads on free sites, so we can't list our address for security reasons. The exact address will be provided to guests when they book their rental.

The map is at street level, so please zoom it out a level or two and scroll north or click the up arrow for north to see where we are at relative to downtown and McCormick Place. McCormick Place is located at Cermak Road (22nd St) and Lake Shore Drive which is 2.8 miles northeast of our rental.

When the map loads, you can click "get directions" to enter an address or "search nearby" to search for most of the attractions that most people want to go to such as Navy Pier, Millenium Park, our Museums, the theatre district, and stores on our Magnificent Mile shopping area on Michigan Avenue.

Transportation to downtown and the near north area of the city is simple. It is a 10-20 minute drive or cab ride even in rush hour to all of our major attractions. We are very convenient to McCormick Place (1 train stop), the museums (2 train stops), Milennium Park (4 stops) and all of the great sights of Chicago. We are less than a 5 minute walk to U.S. Cellular Field, home of the Chicago White Sox. Ours is also a quiet residential neighborhood where you won't hear sirens or car horns all night like some parts of the city.

Another benefit of staying with us is that one parking space in our 2 car garage is included


The City of Chicago has a new local ordinance that regulates vacation rentals.

We are a legal vacation rental and our license number is 2074660.

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.

Bob C

Area Information
This rental is located just South of Downtown Chicago in a quiet and very safe neighborhood. It is an easy trip to downtown, the Museum Campus, and all of our city's attractions. McCormick place is less than 10 minutes away and it's 10-15 minutes to downtown. If you are coming for a show at McCormick Place, please let us know and we'll send you the specific travel information.

Our neighborhood is quiet and safe. 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 real estate site Zillow that says it 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 as "really a family neighborhood."

About the owner

Owner Profile

Bob C

Bob C

Bob C

  • School:

  • Work:

    Investments and consulting
  • About:

    We are two long time friends who bought this building together and lived in it for the first 8 years before we converted it to a vacation rental in 2007.

    We have been listed with this site continuously since October 2007.

    We are both lifetime Chicagoans. Feel free to ask us for a copy of our...
  • View full profile



Begins Ends Week
Weekly Monthly Min
Mar 01 2017 May 15 2017 $180 $210 $1,250 - 3 Nights
May 16 2017 May 22 2017 $210 $220 $1,275 - 4 Nights
May 23 2017 Sep 03 2017 $235 $245 $1,650 - 4 Nights
Sep 04 2017 Dec 01 2017 $190 $210 $1,350 - -
Check In: 3 p.m. Check Out: 10 a.m.
Lodging tax: 16.4%
Deposits: RESERVATIONS require 1/3 to 1/2 of the total cost. The balance is due 30-45 days prior to arrival A $200 Refundable Security Deposit, our cleaning costs and lodging taxes are included in the quote we send when we respond to your inquiry. We always have a range of rates. There is no one rate. Your rate will depend on the season, the length of your stay, major holidays and other factors. We will quote you our best all inclusive rates tailored to your group when we respond to your inquiry.
Payment Options: American Express, Discover, Mastercard, PayPal, Visa
Other Fees: Summer rates from Memorial Day through Labor Day are $220-$270 per night. That includes lodging tax and our cleaning costs. The cost will depend on the timing and length of your stay. We don't rent to adults under 30 years of age or for parties of any kind. Occasionally we will make slight exceptions on the age limit for responsible adults who are 25 and older and not coming here to have a party. Our guests appreciate that we have a quiet and peaceful environment.

Reviews (4)

Reviews for this vacation apartment rental in Chicago, Illinois

Have you been a guest of this property? Write a review!
4 reviews
Julene Jones

Perfect in every way!

Julene Jones


Perfect in every way!

July 10, 2013

This condo was absolutely perfect for my week and a half stay: quiet, clean, and fully stocked with standard items. Bob could not have been nicer: he provided tips on things to visit, restaurant recommendations, directions and grocery shopping information, plus a youtube video tour, and was very clear that he was available for any additional questions / problems we might have had. Having the roof deck, the hot tub and the steam shower were really great extras, and were all well-maintained. My husband and I will definitely stay here again, as the owner, and this condo exceeded our expectations!

Bob C

Owner's reply:

Thank you so much Julene. We are glad that you had a great time. This was our home for years and we are happy when a guest enjoys being there as much as we do.


Like being at home


Ann Arbor, Michigan

Like being at home

October 11, 2010

Bob was great to work with and provided a lot of helpful information both written and online to make the stay in his unit easy. The unit itself is spacious and included all the amenities one would expect and even more considering you have a 65" HDTV and surround sound. The unit is in a very nice working class neighborhood with several local restaurants and bars within a few minutes walk. The food prices were well below the average for a city such as Chicago however, the taste and quality were exceptional. I shared the unit with a coworker and having two bedrooms made it easy to share. The unit is very quiet and even though my bedroom was closest to the living room, when I was in the room with the door closed, I did not hear the television. I've stayed in many hotels in Chicago over the years and certainly Bob's condo was by far one or, if not the best, I have experienced. I would highly recommend the unit to anyone visiting Chicago especially if you are going to be staying for any extended period of time. I was there for eight days and enjoyed being away from the rush of the downtown area.


Great place!


London, UK

Great place!

September 10, 2010

Great place, with lots of room and everything you could ask for. Big kitchen, nice dining room, huge living room, hot tub, rooftop terrace, etc. We took the subway into the city and it was super convenient.

Darren Olson

Amazing value and landlord

Darren Olson

Toronto Canada

Amazing value and landlord

May 28, 2010

First of all, right from the beginning I cannot say enough about the owner, Bob. This guy is a true gentleman, worthy of a great compliment. Never have I felt so comfortable in my years of travelling to 54 countries. Bob, even the owners of the Diner, Benny loves you. What can I say. This home makes you feel at home in every respect. I slept like a baby and woke up like a prince. Thank you Bob

Owner Supplied Testimonials

These Guest Reviews were copied from our other ad on this site (Listing 31547) which has been active since 2007.

Most of these reviews reflect the other apartment in the same building, which is a 3 bedroom, but many of them are from guests who stayed in this apartment.

These were all submitted by the guests themselves and were unedited.

an actors home away from home, March 3, 2010
By kevin Loomis (nyc)
three actors that were touring with the musical 101 dalmatians stayed here for two weeks. bob couldnt have been nicer! quiet, near public transpo to the city, a kitchen made for cooking, satellite tv, stereo, a steam shower, and the crowning jewel: THE HOT TUB. which these weary actors used EVERY night. it soothed away our troubles. washer and dryer conveniently located on the property, no keys needed on the coded door, etc. etc. we hated to leave.

Chicago rental, January 12, 2010
By Kathleen (Laois, Ireland)
Spacious home just a stones throw from the train line to the city, perfect for groups or families, shall I be traveling in a group again I shall definitely be looking this one up.

Chicago apartment, November 15, 2009
By Leo & Nicole Sanders (Rowlett, Texas)
We absolutely loved the apartment rental! It had everything we needed, it was a home away from home. It was very kid friendly! The large steam shower, and jacuzzi were fantastic! The location was very close to downtown Chicago so it was very convenient. If I'm lucky enough to return to Chicago I would absolutely stay there a again!

great apartment, August 21, 2009
By Pam (Reno NV)
This place is awesome! great views from the rooftop deck day or night... great hot tub.. no noise from the street- it's a safe and clean neighborhood. Easy walk to the redline which takes you anywhere you want to go. Located blocks from the 94/dan ryan expressway for easy car access all over the area. (again, no noise at all)VERY FAMILY FRIENDLY! our 7 year old had a blast. It was home away from home for us. We would most certainly stay here again. Thank you Bob for such a pleasant experience.

Kehli's Birthday, May 30, 2009
By Sherri Fearing (Lancaster, Virginia)
This was the perfect house for our family to meet and celebrate our daughter Kehli's birthday. Very child friendly and had everything we could want to cook our own meals. The hot tub was awesome and the roof paio was a treat. Couldn't have a had a better view of the fireworks each night from the Sox games.Bob was incedibly helpful and a pleasure to deal with.Oh yeah.. I almost forgot the wonderful steam shower. WOW. We would definitely rent thee next time we visit Chicago. Thanks Bob! Sherri

Great rental home!, May 29, 2009
By Kehli Saucier (Rochester, MN USA)
We had such a wonderful experience, the true feeling of living in Chicago. This was a wonderful place to come home to after sightseeing. There were all the comforts of home down to the cooking spices. The luxury items were fantastic as well. The rooftop patio, hot tub and steam shower were a big hit. The walk to the L was easy. There were games every day, but there was still street parking. The use of the garage was nice though. The internet and satellite tv were extra pluses. Thank you for such a comfortable stay!

Review- chicago house rental, December 7, 2008
By Anil Singhal, MD (San Jose, CA)
Excellent space. good size, fully equipped. Love the lock system for entry - avoids issues of lost keys! Bob very helpful and hands on if needed. great shower and hot tub. nice neighborhood.

great place!, October 16, 2008
By PAblo Weyler (Buenos Aires, Argentina)
Great Place when visiting Chicago! Lots of space, nice and quiet neighborhood near downtown. I definitely will come back here when visiting Chicago! Jacuzzi and steam are a plus! Thanks for everything Bob!

Great place to stay especially for baseball fans, October 7, 2008
By Cindy Sloan (Kansas)
This apartment worked out really well for our family. Our teenage sons had plenty of room and loved the TV and computer. It's in a nice neighborhood and really close to US Cellular field. It's great to walk out the front door and down the street to see a Major League baseball game, even if you're not a White Sox fan (we're not but love watching baseball). The kitchen is fantastic and the shower is relaxing. There's a huge hot tub and a washer and dryer. The owner is really nice and helpful. Just a great, affordable place to stay in Chicago!

wesome!, October 2, 2008
By Harriet (Kingston, NY)
What is there not to like about coming home to Bob's/our away from home after having stomped all over Chicago, and ending up in a hot tub with jets full blast! AND the rooftop which we caught both views of fireworks from the Navy Pier (far away), and U.S. Cellular field(close-up! The attention to the appliances (top of the line), and bathroom (sauna) are wonderful! What a find!

A most convient stay, September 28, 2008
By Lloyd Hastings (Cincinnati, OH)
Our stay at the apartment was most enjoyable. The accommodations were spacious and very comfortable. The kitchen was very well equipped and had all the amenities. The apartment is in a well maintained neighborhood and is convient to the downtown, the museums, McCormick Place, etc. Bob the owner goes out of his way to make sure one's stay is most pleasant. I highly recommend.

Excellent value, September 9, 2008
By Dan (Saint Paul, MN USA)
This space has everything that you need for your Chicago visit. You'd think that parking might be an issue when there are White Sox games but passes are provided and there is even access to a separate parking area in case the street fills up while you're out on the town. You're close to the Red Line and US Cellular Field. The place itself has wireless, a luxurious shower, beautiful roof deck and the hot tub is great too. Would use again and recommend to anyone.

Live Like a Local...., July 10, 2008
By Paula Davis (Satellite Beach, FL)
We recently went to Chicago for a 3-day conference and decided to rent a condo where we could stay for a week for less than we would have paid at a hotel for 4 days. We were fortunate to find this great place where we could live like locals and experience Chicago in a way we would not have been able to do by staying in a hotel. Bob's condo is in a lovely eclectic neighborhood that is just a couple blocks from Cellular Stadium and easy access to public transportation and quaint corner markets. The condo has all the comforts of home - a beautiful gourmet kitchen with state-of-the art appliances and cookware; a big-screen TV and music center; computer with Internet access and best of all, a huge hot tub that was a welcome treat on our convention weary bones. Everything was very clean and in good working order and things like coffee, tea, paper products, shampoo, soap, etc. are generously provided. We hope to have another chance to visit Chicago and would definitely stay here again.
Like a slice of home..., April 11, 2008
By Craig (San Francisco, CA USA)
This was my first time renting a condo instead of staying at a hotel while on vacation, and I've got to say...this is the way to go! The place was great and had that homelike feel that you never get in a hotel. The kitchen was superb and the shower was super awesome. It has those crazy body jets and a steam option. Super relaxing, but if that wasn't relaxing enough, there was the hot tub. This thing was almost big enough to swim in and trust me that's huge! We spent a good amount of time in the hot tub, which was nice since there was a blizzard outside. The condo was also in nice location and the freeway was just down the block, making it easy to get around. When I come back to Chicago, I am definetly staying there again. Don't miss out a great experience and spend your hardearned cash on a lousy overdecorated hotel, when you can stay in a little slice of home.

Home Away From Home, April 5, 2008
By James Krueger (Michigan, USA)
The six of us stayed comfortably. We utilized the wonderful kitchen in order to save money. After long days of museum visits we loved relaxing in the hot tub. The neighbors were quiet and the neighborhood safe. We chose to walk the short distance to the Red Line train each day as we ventured into Chicago with our children - with planning, it worked out well for us. The children are already asking to stay here again soon!

I really recommend this place!!!, March 26, 2008
By Natalie Hudson (Las Vegas, Nevada USA)
My husband and I travel a lot, but we don't have a lot of money, so we always try to find the nicest place we can find at the cheapest price. This place is definitely a great bargain and well worth the money. I can say it is one of the nicest places we have ever stayed at. It is very big with all the extras you can imagine: big comfy beds, spa shower (like a massage), Internet, laundry, and more. It is a home, not just an empty rental. It is also VERY well stocked. You won't need to go buy anything while you are staying here. It is in a safe neighborhood very close to public transportation. A really frequent bus (every 9 minutes) comes by a block away and takes you right to the subway/train which takes you anywhere. One of the biggest perks is the truly kind and helpful owner, who always answers his phone and helps you with anything you need. I'd stay for his helpfulness alone.

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