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Member since: 2007
Speaks: english

Luxury and Value. Very Safe Area. Skyline View. McCormick Place. Hot Tub Parking

Bedrooms 2
Half Baths1
Property type apartment
Minimum Stay 3 - 6 nights

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South Side Apartment Rental Photos and Description

2 Bedrooms + Other (See Description), 1.5 Baths Sleeps 6

We have 2 beautiful apartments that have fantastic extras and a great value. We have 8 years of 5 star reviews. We are close to all of the great attractions of Chicago.

We are offering a special for late August and early September. 3 nights are $595 and extra nights are $105 each.

From April through November, we have an outdoor roof deck with an amazing Chicago skyline view. We also have a fantastic huge hot tub and a large 5 foot by 3.5 foot steambath shower. They are both great place to relax after a day of travel, sightseeing, or business. You can see this in our pictures section.

Many of our guests come for trade shows at our convention center, McCormick Place. It's a quick 7 minute drive or Uber and 1 stop on the train.

Our guests expect and enjoy a quiet location to enjoy their vacation or business trip. We are on a very quiet and peaceful residential street.

If you are requesting a Saturday arrival or Departure, please email us first before submitting a reservation request. We only offer Sat arrival or departure on a small number of dates.

If this apartment is booked, or if you have a larger group, we have a second apartment in this building that may be available. If you rent both apartments, you will be renting the entire building.

Our first floor apartment is listing number 225815 on Homeaway. Put that in the search box on the top left and erase whatever else is there.

This Apartment has 2 bedrooms and 3 queen beds and sleeps up to 6 guests. We have a huge living/entertainment room where we have a queen sleeper sofa as our 3rd queen bed The living room is at the far end of the apartment and anyone sleeping there has a lot of privacy. We also have a queen air bed that can be set up for one extra sleeping space. We have fully stocked modern kitchens.


Our rentals are located just South of Downtown Chicago in the quiet and safe neighborhood of Bridgeport. 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 one of the safest neighborhoods in Chicago. 5 of our last 8 Mayors spanning 90 years came from our small neighborhood

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 web 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 dot com as 'really a family neighborhood.

Our easy access to our city center, McCormick Place , and I.I.T, has made ours a very hot residential destination for the last 15 years. One of our neighbors recently built a $2.5 million house and next door is a huge house with an indoor swimming pool in it's own addition that is now for sale for 1.7 million. New construction and completely renovated buildings like ours are the norm. Ours is a very quiet and peaceful block.

We include one garage parking space with your rental.

We offer discounts for longer rentals.

Our apartments are available for lodging only. We do not rent our apartments for parties or gatherings of any kind, or to groups coming for music festivals or concerts. Loud noise late at night or excessive noise anytime is not tolerated. Our rentals are a very bad fit for the heavy partying or very late night crowd. Our guests appreciate that we have a quiet and peaceful environment

We prefer that the guest renting the apartment is 30 years of age or older. We are willing to discuss rentals with responsible adults 25 and older.

The maximum capacity of the apartment is 6 persons. The apartment has 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 if there are infants or very small children.


The City of Chicago has an ordinance that regulates vacation rentals.

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

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.

Thank you for taking the time to read through all of the very detailed information in our ad.

We want all of our guests to know exactly what the details of the rental are so that their expectations are met and that this is a good fit for both of us. We try very hard to make sure that our guests have an excellent stay and do all that we can so that you enjoy our beautiful city

More Details
  • Long-term Renters Welcome
  • Low Allergen Environment
  • Minimum Age Limit for Renters
  • children welcome
  • non smoking only
  • pets not allowed
  • wheelchair inaccessible
Bob (Owner)
Member since: 2007
Speaks: english

About Bob

We are two lifelong friends who bought this building to live in, remodeled it completely for ourselves, and later converted it to a vacation rental.

Bob purchased this apartment in 2000

Why Bob chose Chicago

Our area is safe and very close to everything in Chicago, including our convention center, McCormick Place. You are in a quiet and safe neighborhood, but the city center and all of our major attractions are very close. It's the best of both worlds.

What makes this apartment unique

You will love our deck with the amazing view of the Chicago city skyline, our hot tub, and our huge steam bath shower with multiple Grohe Body Sprays. It is like a massage.

We are ½ mile from the I-94 Dan Ryan Expressway. It is a 5 minute drive to Lake Shore Drive and another 10-15 minutes from there to the Museums, Navy Pier, Millennium Park, Michigan Avenue shopping and every major attraction in this city.

When we lived in this building ourselves, we would always be able to get to the lakefront and all of our major attractions in 10 to 20 minutes. If there is a concert, or major festival on the lakefront. we can show you a local shortcut to make great travel time to our city center.

Ours is a quiet, safe, and friendly family neighborhood. We have great 3 to 4 star restaurants and bars and great casual dining with every infamous Chicago sandwich and pizza that you've heard of. You can save a fortune on casual dining or drink prices if you want to eat locally some of the time during you visit. You can park easily too and we include garage parking with your rental. If you want to visit our 5 star restaurants or nightclubs, they are a quick 10-20 minute drive or cab ride away.

Guestbook comments from the owner

Although this is one of our newer ads that began in 2011, we have been operating our rentals since October 2007.

Please see our many reviews at our other Home Away Listing # 225815

Here is one of the guest comments from our early days.

By Natalie, Las Vegas

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 with necessities. It is in a safe neighborhood very close to public transportation. 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. I really recommend this place!!!
Mar 2008
  • 1 of 1


Wonderful! 4.9/5 -
(35 traveler reviews)
Luxury and Value. Very Safe Area. Skyline View. McCormick Place. Hot Tub Parking
average rating of 4.885714 based on 36 reviews

Perfect Location!

  • 5 of 5

This was a perfect location for all we planned to do downtown. Very roomy property and a suoer reasonable price. Steam jetted shower was great. it was nice to have a fully equipped kitchen so we could save a bit on dining out. This property also included a garage for parking. we left the car there and used Uber for everything else. getting into heart of downtown was only 12 bucks. well stay here again on our next trip to Chicago!!

  • Submitted: Aug 23, 2016
  • Stayed: Aug 2016
  • Source: HomeAway
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Great House and Location

  • 5 of 5

This was my first time in Chicago and I was accompanying my husband on a business trip. Since he had to stay for almost a week, we chose to get a VRBO instead of staying in a hotel. I was really hoping to stay downtown, but the location of this place was perfect. We walked around the area and found some amazing restaurants and bars that were super close. And it was a quick Uber or train ride to get downtown. We could not have been happier with the location. The place was clean and very big. Bob was quick to answer any questions and the videos were helpful. It was a great stay in a great City!

  • Submitted: Jul 26, 2016
  • Stayed: Jul 2016
  • Source: VRBO, from HomeAway
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Sox & Lakeshore Luxury

  • 5 of 5

House was as described, very close to MANY area attractions that my family and I were looking to take in! Owner is very agreeable, fair, and easy to communicate with! I would definitely recommend this property to anyone looking to spend some time in the area - we will definitely stay here again when we return! Thanks again!

  • Submitted: Jul 1, 2016
  • Stayed: Jun 2016
  • Source: VRBO, from HomeAway
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A large space, in a quiet neighborhood. Perfect!

  • 5 of 5

Our family of four stayed at Bobs recently and had the prefect time. We were in town for an event st McCormick place and this location was perfect. The apartment has a rooftop deck which we loved- amazing views and the perfect outdoor eating, couch reading escape. The inside has huge common areas. The bedrooms are small with dated linens, but we spent our time in the large living room, dining room and fully stocked kitchen. Bob was so attentive to any question we had, helpful with details about the house and the area, throughout our stay. We felt at home immediately. Thank you Bob!

  • Submitted: May 28, 2016
  • Stayed: May 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thanks for your nice comments Cassandra and for bringing the bedroom duvets to our attention. The previous guest had washed them with bleach and stained them. Our property manager was supposed to replace those and dropped the ball. All of the duvets in the apartment have been replaced.
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Lexington, Kentucky

Look no further! A wonderful find in Chicago

  • 5 of 5

I chose this location based on reviews and I was not disappointed. The location is a quick walk to train station. The owners are very helpful and there were lots of extra trip items at the location. While the weather was not pleasant; coming back to a nice sauna shower was fantastic. The bed was incredibly comfy and we have traveled to many places. Also, the garage is a money saver in Chicago. Vacation searchers this is a great place.

  • Submitted: May 3, 2016
  • Stayed: Apr 2016
  • Source: HomeAway
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Great value and location

  • 5 of 5

This was a great base for all the things we wanted to do. The place itself was simple, but clean and quiet. Things were placed where you expect them to be -- scissors in the drawer, detergent next to the machine. You don't waste time hunting for items. For planning, it was nice having the long dining table to spread out our papers. The one bathroom was fixed up with a great steam shower, and multi-shower heads. The kitchen is well-stocked with cooking utensils and cooking supplies (oil, sugar). We appreciated having the washer/dryer right outside the kitchen. Location-wise, it is close to Comiskey Park, the freeway, Soldier Field and the main museums (Fields/Adler/Shedd). We didn't get around to using everything that was available at the rental, but we would definitely stay here again.

  • Submitted: Feb 16, 2016
  • Stayed: Jan 2016
  • Source: VRBO, from HomeAway
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Nearest Airport
7 Miles
Midway Airport
Nearest Barpub
0.25 Miles
Shinnick's Bar
Nearest Golf
8 Miles
Sydney Marovitz. The Pebble Beach of Chicago
Nearest Train
0.5 Miles
Nearest Motorway
0.5 Miles
Interstate 94 at 35th Street
Nearest Restaurant
0.4 Miles
Schaller's Pump bar and grill
Nearest Beach
3 Miles
31st Street
Car: not necessary

The map in this ad can be zoomed in or out to see how close we are to downtown Chicago and all of the great attractions that this city has to offer.

Here is a list of some of the great attractions and activities in Chicago. We have included some links to their websites or you can easily find them in google or any search engine.

Navy Pier, Millennium Park Architectural Foundation Tours, American Girl Place Museum of Contemporary Art The Art Institute of Chicago The Field Museum of Natural History Museum of Science and Industry Chicago White Sox Chicago Cubs Chicago Blackhawks Hockey Chicago Bulls basketball Taste of Chicago Lyric Opera Chicago Symphony Orchestra Adler Planetarium Brookfield Zoo Buckingham Fountain Chicago Air and Water Show Chicago Blues Festival Chicago Cultural Center

Harold Washington Library Center Lamb's Farm Lincoln Park Zoo

Michigan Avenue/Magnificent Mile Shopping Ravinia Festival Concerts Willis Tower Skydeck Shedd Aquarium Six Flags Great America The John Hancock Observatory The 96th Floor Lounge at the John Hancock Center Shopping at Water Tower Place on Michigan Avenue

Chicago is known for it’s great festivals such as the Blues, Jazz, Gospel fests as well as the Taste of Chicago, and our Air and Water show.

If you are going to try to visit the museums and other major attractions, the Go Chicago Card can be a great value.

Here are some of the 26 major attractions that are included at one price.

• Includes: several walking and bus sightseeing tours,

• Adler Planetarium, Museum of Science and Industry

• John Hancock Observatory, Willis Tower Skydeck

• Shedd Aquarium, Field Museum of Natural History

• Willis Tower Skydeck, Brookfield Zoo

• Lincoln Park Zoo, Chicago Art Institute

• Hop on, Hop off Trolley Tour

• It is a 2 minute walk from our door to U.S. Cellular Field, home of the Chicago White Sox.

• It is also a short walk to the campus of Illinois Institute of Technology.

We are less than 10 minutes from McCormick Place, and less than 15 minutes from the Museums and Grant Park where Millennium Park and Navy Pier are located. We are 2.5 miles SW from McCormick place and 4.5 miles due south from Grant Park and our downtown. If you are coming for a conference at McCormick, let us know when you inquire and we'll send travel information.

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.


Rates & Availability

South Side Apartment Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Aug 2 2016 - Sep 10 2016
3 night minimum stay
September and October
Sep 11 2016 - Oct 20 2016
3 night minimum stay
FALL 2016
Oct 21 2016 - Nov 24 2016
5 night minimum stay
Nov 25 2016 - Dec 4 2016
6 night minimum stay
December 2016
Dec 5 2016 - Dec 20 2016
3 night minimum stay
Holidays 2016
Dec 21 2016 - Jan 2 2017
5 night minimum stay
Winter 2016
Jan 3 2017 - Feb 28 2017
3 night minimum stay
Mar 1 2017 - Nov 30 2017
5 night minimum stay
Winter 2017
Dec 1 2017 - Feb 28 2018
5 night minimum stay
My Standard Rate
4 night minimum stay

Additional information about rental rates

Refundable damage deposit $200

Ours is a 2 unit building. If this apartment is taken, our other apartment may be available and it is listed on Homeaway and VRBO. If you need more space, you can rent both apartments and you'd have the entire building. Our guests who do that really enjoy that.

We have a few main policies that we prefer to discuss up front. We know that these don't apply to 99% of our guests, but we have learned the hard way that these need to be discussed before we reserve a rental for a guest.

We don’t allow parties or gatherings of any kind. We only rent our apartments for lodging. Noise late at night or excessive noise anytime is very disturbing to our neighbors and other guests, so our rentals are definitely not a good fit for the very late night or very hard partying crowd. We do not rent to guests coming for music festivals or concerts. A few groups ruined that for everyone. We are located in a quiet residential area and our guests and neighbors We prefer that the guest renting the apartment be 30 years old or older, but we are glad to discuss rentals with responsible adults 25 and older.

About our rates. We can often offer additional discounts for longer rentals. We set our rates depend on the length and timing of your rental. Some special events may have higher minimum stay requirements or have higher per night rates for shorter rentals.

If you are concerned about having to cancel your trip, we suggest that you look into trip insurance that is available and offered by many reputable firms online and otherwise. One such firm is

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.
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South Side Apartment Accommodation and Amenities

Property Type:
  • apartment
  • floor 2
  • Guests provide their own meals
Floor Area:
  • 1300 sq. ft.
Location Type:
  • Downtown ...
  • Monument View ...
  • Town
  • Budget
  • Family
  • Historic
  • Romantic
  • Tourist Attractions
  • Activities Guide
  • Air Conditioning ...
  • Alarm Clock
  • Ceiling Fans
  • Clothes Dryer ...
  • Computer Available ...
  • Garage ...
  • Hair Dryer
  • Heating ...
  • Internet
  • Iron & Board
  • Laundry Soap
  • Linens Provided ...
  • Living Room ...
  • Local Maps
  • Local Restaurant Guide
  • PC
  • Parking ...
  • Sofa Bed
  • Telephone ...
  • Toilet Paper
  • Towels Provided ...
  • Washing Machine ...
  • Wireless Internet ...
  • Coffee Maker ...
  • Cooking Utensils ...
  • Dishes & Utensils ...
  • Dishwasher ...
  • Kitchen ...
  • Kitchenette
  • Microwave ...
  • Oven
  • Refrigerator ...
  • Stove ...
  • Stove
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 6 people
  • 1 Bathroom
  • 1 Half Bath
  • Bathroom 1 - toilet , shower , Steambath Shower
    Bathroom 2 - toilet , Shared-both apartments
  • Our huge 5 foot by 3.5 foot shower has Grohe Body Sprays and a steam bath generator. Our guests love it. Some of our guests have said that it's like a massage. There is an additional half bath in our basement that is shared by both apartments as a backup
  • 2 Bedrooms, Sleeps 6
  • Bedroom 1 - 1 queen
    Bedroom 2 - 1 queen
    Bedroom 3 - 1 sleep sofa /futon
  • There are two full bedrooms. Our 3rd Queen bed is located in our living/entertainment room. The living room is located at the far end of the apartment and the bed is hidden by a wall. Anyone sleeping there has a lot of privacy.
  • DVD Player
  • Music Library ...
  • Radio
  • Satellite / Cable ...
  • Stereo ...
  • Television ...
  • Video Library ...
  • Deck / Patio ...
  • Outdoor Grill ...
  • Outdoor Grill Gas
  • Patio
  • 6 garden chairs
  • Long-term Renters Welcome
  • Low Allergen Environment
  • Minimum Age Limit for Renters ...
  • children welcome ...
  • non smoking only ...
  • pets not allowed
  • wheelchair inaccessible ...
Pool / Spa:
  • Hot Tub ...
  • Indoor Hot Tub
  • Steam Shower
  • churches
  • cinemas
  • coin laundry
  • library
  • live theater
  • marina
  • museums
  • restaurants
  • synagogues
  • zoo
Leisure Activities:
  • antiquing
  • gambling casinos
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
Sports & Adventure Activities:
  • cycling
  • fishing
  • freshwater fishing
  • golf
  • roller blading
  • swimming
  • tennis
The guest renting the apartment must be 25 years of age or older. If the guests are under 30, we expect responsible adults. Our rentals are not a good fit for the very hard partying or very late night crowd. Our guests and our neighbors 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 our prior approval only.

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