HUGE HOLIDAY & WINTER Specials. Reviews. Hot Tub

Our Luxurious Hot TubIncredible City Skyline View from our deckOur shower with amazing Grohe body spraysClose up of our shower spraysOur living roomDining room table and decorative fireplaceOur kitchen & stainless steel appliances.  View #1Our kitchen view #2 from opposite directionOne of our comfortable bedroomsanother bedroomCedar Closet
“ Excellent ”
25 Reviews
529 W 37th St, Chicago, IL 60609

$140/night - HOLIDAY and winter SPECIAL Lowest Last Min Prices

For stays between 12/17/14 and 1/16/15

Our lowest last minute specials ever. $875 per week, $800 for 6 nights, 725 for 5, 650 for 4 nights. Some dates are available for 3 nights at $575. These rates are available through the end of February.


Bedrooms: 3
Bathrooms: 1.5
Sleeps: 6
Type: Apartment
Per night: $140 - $235
Per week: $875 - $1,475
Pets allowed: No
Internet: Yes
Description of the Chicago vacation apartment rental
Close to Downtown & McCormick Place. It's 10-15 min by car or cab or a 15-20 minute train ride from everything that Chicago has to offer.

Please see our specials ad for our current specials. Our winter specials are our lowest rates of the year.

You will be comfortable and at home in our rentals. We have been offering our rentals for 7 years now. We have over 200 reviews at the different sites that we list at, and we are proud to say that they are all very positive.

We have an amazing 5 star hot tub. It's a great place to relax after a day of travel, sightseeing, or business. We also have a deck with an incredible skyline view of Chicago (closed in winter when there is snow and ice). You will also see pictures of our huge 5 feet x 3,5 feet shower that features Grohe body sprays and a steambath generator. Our guests say that it is like a massage.

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.

This site's quotable rates are often wrong. We set our rates the best we can. Our special rates have deep discounts on extra nights and this site's rate system can't do that. Rates vary from $140 to $260 per night and $975 to $1,675 per week and include all taxes and fees. Rates depend on the timing and length of your stay. There is no one rate. Longer rentals have the best per night rates.

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 3 bedrooms and each has a queen bed. We also have a queen air bed that can be set up for one extra sleeping space. The maximum number of guests is 6 persons. Sometimes we will allow a 7th is you have very small children with you. If you have a larger group, we have two apartments in this building that both have three queen beds. If you have both apartments, you would be renting the entire building.

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

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 have over 200 reviews through the different sites that we list at and we are proud to say that they are all very positive.

The longer your rental, the better per night rate that we can offer you. We always have a range of rates. There is never just one rate. Please inquire with your dates and we will respond with a rate quote for your stay.

We have a 4 night minimum in summer and a 3 or 4 night minimum the rest of the year.

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.

We also have a second apartments available. If this apartment is booked for your dates, that apartment may be available. 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.

Email us with your dates and we'll give you the best deal that we can.

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.

The apartment is also stocked with many of the basic necessities that you will need during your stay such as soap, paper products, laundry soap, etc. We rent ourselves 2-3 times a year. There is nothing that we 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 garage parking is included. We can sometimes offer you 2 spaces when our 2nd unit guests don't have a vehicle.


The City of Chicago has a new local ordinance to regulate 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.
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 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 a real estate site 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."

Availability Calendar


Begins Ends Week
Weekly Monthly Min
Nov 17 2013 Nov 29 2015 $140 $160 $975 - 3 Nights
Nov 29 2013 Dec 04 2015 $215 $215 $1,375 - 6 Nights
Dec 19 2014 Jan 03 2015 $180 $180 $1,050 - 3 Nights
Jan 03 2015 Feb 23 2015 $140 $160 $950 - 3 Nights
Feb 24 2015 May 31 2015 $190 $210 $1,350 - 4 Nights
Jun 01 2015 Aug 01 2015 $235 $235 $1,475 - 4 Nights
Aug 02 2015 Aug 19 2015 $225 $225 $1,475 - 4 Nights
Aug 20 2015 Sep 07 2015 $195 $195 $1,350 - 4 Nights
Dec 05 2015 Dec 18 2015 $140 $165 $875 - 3 Nights
View all periods
Check In: 3 p.m. Check Out: 10 a.m.
Deposits: Our rates depend on the season and the length of your stay. There is no one nightly or weekly rate. We always have a range of rates. The weekday and weekend rates listed for each season are our range of rates for that season. Our Daily rates range from $140 to $195 per night in winter to $225 to 275 per night in summer. Our weekly rates range from $975 to $1,150 in winter to $1,450 to 1,650 per week in summer. All taxes and fees are included in our rates.
Payment Options: American Express, Discover, Mastercard, PayPal, Visa
Other Fees: Our best rates are for longer stays. Shorter stays are priced higher due to fixed costs. Winter is our lower rate season and Summer is our high season rates. We require a $200 refundable security deposit with each rental. The guest renting the apartment must be 30 years of age or older. We don't rent our apartments for parties of any kind. Occasionally we will make exceptions on the age limit for families with children and responsible adults 25 and older who are not coming here to party


  • Beds

  • 3 Queen Beds
  • Features

  • Air Conditioning
  • Hardwood Floors
  • High Speed Internet
  • Parking Included
  • Deck
  • Heating
  • Hot Tub
  • View (City Lights)
  • Full Kitchen
  • Appliances

  • Alarm Clock
  • Dishwasher
  • Oven
  • TV (Cable/Satellite)
  • CD Player
  • Gas Grill
  • Radio
  • Telephone
  • Ceiling Fan
  • Hair Dryer
  • Refrigerator (Full)
  • Toaster
  • Coffee Maker
  • Ice Maker
  • Stereo
  • VCR
  • Computer
  • Microwave
  • Stove
  • Washer/Dryer
  • DVD Player
  • Activities

  • Basketball Court
    (<1 mile)
  • Restaurant
    (<1 mile)
  • Aquarium
    (3 miles)
  • Zoo
    (8 miles)
  • Bowling
    (<1 mile)
  • Shopping Area
    (<1 mile)
  • Boating
    (3 miles)
  • Casino
    (15 miles)
  • Grocery Store
    (<1 mile)
  • Children's Pool
    (1 mile)
  • Golf
    (4 miles)
  • Horseback Riding
    (15 miles)
  • Gym/Fitness Center
    (<1 mile)
  • Beach
    (2 miles)
  • Ice Skating
    (4 miles)
  • Water Park
    (20 miles)
  • Park
    (<1 mile)
  • Fishing
    (2 miles)
  • Live Entertainment
    (4 miles)
  • Amusement Park
    (25 miles)
  • Playground
    (<1 mile)
  • Hiking
    (2 miles)
  • Movie Theater
    (4 miles)
  • Theme Park
    (25 miles)
  • Racquetball
    (<1 mile)
  • Lake
    (2 miles)
  • Sailing
    (4 miles)

Other Vacation Rental Amenities
McCormick Place, Illinois Institute of Technology, Downtown Chicago, Millenium Park, and the Museum Campus are all nearby within 10-20 minutes. U.S. Cellular Field is 1/4 mile away. The University of Chicago is 15 minutes away.

Reviews for this vacation apartment rental in Chicago, Illinois

Have you been a guest of this property? Write a review!
Sonia Mejia

Oceanside CA

Outstanding Accommodations

I want to give thanks to Bob for giving us the opportunity to stay at his vacation rental. It was in the perfect location and close to everything. We were able to sit up on the roof and watch the fireworks and for those rough days we could sit in the spa and the shower and sauna in the bathroom was amazing. I completely recommend this home for a long term and even short term vacation. Thanks again.

Bob C

Owner's reply:

Thank you Sonia for your very nice comments. This was our home before we converted it to a rental. We are very happy when our guests really enjoy it too. You mentioned the 3 things that were my favorites, the skyline view from our deck (I was up there last week), our 5 foot by 3.5 foot steambath showers with multiple sprays, and our hot tub. We had our first snow and our first below freezing temperatures. It would be a great day for the hot tub.

Gianfranco Pezzino

Topeka, KS

Best service, excellent value

Property is as advertised, kept in very good condition. Location is not central, but neither is the rental price! The L train is less than 15 minutes walk, and the bus one block. Owner is extremely kind and helpful. We were there with a family of 6 and had all the space we needed. Overall, great experience.

Cheri Kannarr

Davis, CA, USA

Great home away

Excellent value, perfect location close to bus and trains, lots of space & extras. We arrived after a week in hotel rooms & were so happy to find this lovely space. The owner, Bob, was incredibly friendly and welcoming. Most staples provided in the kitchen & laundry room. Roof-top dining with fireworks provided by near-by White Sox stadium. Very kid-friendly with board games, Internet, cable TV. Will definitely remember for our next Chicago visit.

Cami Linke

Minneapolis, MN

"You at Bob's place?"

For our family of 6 (16,13,11,2) this rental property fit the bill. Our vacation was to see and do Chicago, but with 4 kids, the expense of a downtown hotel squandered our plans..until I stumbled upon the add for this rental. It was easy to locate off the freeway, convenient to the red line (walking distance)but most of all clean and spacious. Bob thinks of everything you would need or ask, and it's printed out and provided at the rental. Parking was a snap-either on the street, or in the garage (included in the price of the rental). The kids loved the large screen TV, the roof top deck and hot tub. I loved the updated kitchen, cute quiet neighborhood, and the sweet lady at Kathy Dee's deli who asked, "you at Bob's place?" and gave me something I needed "free of charge". I've been to Chicago 4 times now, and I love it more and more with each trip. Wonderful city, wonderful people. You wont be disappointed if you stay at Bob's.

Susan Ziegler

Elk River, Minnesota

Great Windy City stay

My husband and I and our four kids stayed for a full week at this location in Chicago. The rental was everything we hoped for. It was very clean and comfortable, and well stocked with everything we needed. I can't think of a single item we wished we had had. There was even a large stock pot big enough to make a giant batch of my families favorite soup. Having the washer and dryer was fantastic. It allowed us to bring so much less clothing and luggage over all. The most outstanding feature was the rooftop deck. It was such a peaceful spot to sit and gaze at the beautiful downtown skyline at night. We could even see some of the Navy Pier fireworks from up there. The location was perfect for accessing public transportation;once we parked our car in the safe garage space this rental included, except for a couple of trips to the grocery store, we didn't move it all week. It was so nice to not have the hassle of driving and trying to find our way around the city and deal with parking. Overall, a great experience!


Hannibal, MO

Girls weekend!

I hosted a girls weekend in Chicago for 8. We rented both apartments for the weekend and TONS of space, we don't pack light either! It was a little out of the city, but we actualy enjoyed the peace and quite on the street. The owners were very nice and accomadating as well. Anything you could possibly need was there. Also, take a visit to Schaller's Pub down the street, great family owned bar and super nice people and CHEAP, good, food. They actualy offered us a ride when our cab never showed up! We will for sure stay here again on our next trip to Chicago.


Springdale, AR USA

Great! Comfortable and homey place to stay!

My family of 6 visited Chicago in June. We stayed at Bob's place and had a wonderful time! The apartment was spacious and homey. Not to mention, the steam shower was incredible and so relaxing. My family thoroughly enjoyed our stay and we will stay there in the future when we come back to Chicago!


Fairborn, OH USA

wedding / vacation

We were traveling from southwest Ohio to Chicago for a wedding and decided to spend the week and see the city. we had 5 adults and 2 small children and this condo was amazing it fit all of us comfortably, we were happy with the great space, hot tub and amazing view from the roof deck. i felt extremely safe in the location and enjoyed the local food vendors. i would most definitely pick this condo again if i would return to the city. the stay was so great i didn't want to come home. thanks again for such a beautiful place to stay.

kevin Loomis


an actors home away from home

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.


Laois, Ireland

Chicago rental

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.

Leo & Nicole Sanders

Rowlett, Texas

Chicago apartment

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!


Reno NV

great apartment

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.


St. Louis, MO USA

Great Place to Stay

The rental is perfect in so many ways. It is in the middle of a beautiful neighborhood, which is much cheaper than staying downtown. Bob, the owner, is prompt and courteous to deal with. It feels much more like a home than a hotel or coporate rental ever could. Would recommend anyone to stay there. Good view, fabulous amentities, and the kitchen has everything you need to create great meals. The hot tub is big, the shower is great, and the apartment has plenty of space.

Faye Koo

Manila, Philippines

best for business trips

The house is near the McCormick Place so t is very suitable for business trips. It is also a good place to stay for vacations because the neighborhood is safe and quiet. Bob is very accommodating and easy to talk to. He answers every call and email immediately. I highly recommend this to everyone. Especially those who are travelling for business in the McCormick Place.

Sherri Fearing

Lancaster, Virginia

Kehli's Birthday

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

Kehli Saucier

Rochester, MN USA

Great rental home!

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!

Anil Singhal, MD

San Jose, CA

Review- chicago house rental

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.

PAblo Weyler

Buenos Aires, Argentina

great place!

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!

Cindy Sloan


Great place to stay especially for baseball fans

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!


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 Wrigley field( close-up! The attention to the appliances (top of the line), and bathroom (sauna) are wonderful! What a find!

Lloyd Hastings

Cincinnati, OH

A most convient stay

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.

Paula Davis

Satellite Beach, FL

Live Like a Local....

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.


San Francisco, CA USA

Like a slice of home...

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.

James Krueger

Michigan, USA

Home Away From Home

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!

Natalie Hudson

Las Vegas, Nevada USA

I really recommend this place!!!

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.

Owner Supplied Testimonials

We received this comment from a guest and we'd like to share it.

Comment Text: As we wanted to spend our Xmas holidays in Chicago with our children, we decided to rent a flat . We found several flats to rent in town, but we have to say that Bob was the only owner who was friendly enough to answer all our questions and emails and to take time to make more pictures of his flat for us.

Hence we were completely confident that the flat would be nice and comfortable and even discovered that it was better than we thought: great multi-function shower, hot tub, great roomy kitchen and a computer with internet access. Bob also made a wonderful work to leave a extensive documentation about transportation, shop and restaurants which was really helpful. We can highly recommend you this apartment, where we had a wonderful time. Thank you Bob, we will certainly come again !

Another guest comment from a different site that we'd like to share.
I really recommend this place!!! By Natalie 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 much of 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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Page Views This month: 208 This year: 3,302 Since listed: 41,207
Last updated: December 17, 2014

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Owner Profile

Bob C

Bob C


More about the owner
  • 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