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Great Value. Near All Attractions and McCormick Place. Very Safe. Skyline Vie

73 Reviews
Bedrooms 3
Half Baths1
Property type apartment
Minimum Stay 3 - 5 nights

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Half Baths
Minimum Stay
3 - 5 nights


South Side Apartment Rental Photos and Description

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

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

We have a deck with an amazing Chicago skyline view. That is the first picture that you see in our ad. We also have a fantastic huge hot tub and a large 5 foot by 3.5 foot steambath shower. They are all great place to relax after a day of travel, sightseeing, or business.

Many of our guests come for trade shows at our convention center, McCormick Place. It's a quick 7 minute drive or 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.

You can find our other apartment by putting the listing number 271945 into the search bar at the top left of the page. Erase anything else that is in that box first.

This Apartment has 3 bedrooms and 3 queen beds and sleeps up to 6 guests. 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 risk

How close we are to everything and how safe our area is has made ours a very hot residential destination for the last 15 years. New construction and completely renovated buildings like ours are the norm. We are located on a very quiet and peaceful block.

We include one garage parking space with your rental. Street parking in our area is also very easy.

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 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 for groups with infants or very young children.

We will offer discounts on longer rentals. Convention and special event dates may also be priced slightly higher or have a higher minimum night stay.

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


The City of Chicago has a law 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.

More Details
  • Long-term Renters Welcome
  • Low Allergen Environment
  • Minimum Age Limit for Renters
  • children welcome
  • non smoking only
  • pets not allowed

Member since: 2007
Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
October 21, 2016
Call Owner

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 building is 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, even in traffic. 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 and skip any traffic.

Guestbook comments from the owner

This comment was emailed to me from a nice family that stayed with us at the end of September, 2008.

We all had a marvelous time at your condo! It doesn't get much better than stomping all over Chicago, and arriving "home" to a hot tub...and then seeing fireworks from the Navy Pier and stadium from the rooftop! You have definitely invested in all the important items (kitchen and bathroom appliances and hot tub). Everything else was comfortable (furniture, bedrooms etc.). If we are returning to Chicago, we shall definitely contact you first.
Sep 2008
  • 1 of 2


based on 73 traveler reviews

Great Value. Near All Attractions and McCormick Place. Very Safe. Skyline Vie
average rating of 4.917808 based on 75 reviews

Great place to stay.

  • 4 of 5

We were in Chicago for our son's wedding. The owners were very accommodating with plenty of up front information about the rental. When I had questions, emails were returned promptly. After booking, my daughter and her kids also asked to stay for one night. Since we were still within the capacity limit of the rental, the owners accepted this change with no hassle and no extra cost. The kitchen was well equipped and the rest of the unit was comfortable. Parking was tight but we always had a spot in front of or near the unit. I would recommend this unit to others.

  • Submitted: Sep 14, 2016
  • Stayed: Aug 2016
  • Source: HomeAway
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Great place to stay in Chicago

  • 5 of 5

This was a very safe and comfortable place to stay and centrally located to where we wanted to visit (downtown and Hyde Park).

It's not a place to hold a party but a place to relax between quick uber rides so it was perfect for the five of us.


  • Submitted: Sep 9, 2016
  • Stayed: Aug 2016
  • Source: VRBO, from HomeAway
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  • 5 of 5

This was the perfect vacation home! Safe location, near everything but far enough away from things to feel like home. Spacious with top of the line amenities!! We loved it!!

  • Submitted: Aug 27, 2016
  • Stayed: Aug 2016
  • Source: VRBO, from HomeAway
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Cool and comfortable house in Chicago

  • 5 of 5

The house was really comfortable for the four of us. The kitchen was well equipped, there were plenty of bath towels, and the steam shower was really great - even in the heat (fabulous if you take a steam while having a cool water shower). Bob was really helpful when we needed him. The location was great - super close to the baseball field and walking distance to bars and shops (be sure to check out the deli just around the corner). Great place. Would definitely get this home again when/if we return to Chicago.

  • Submitted: Jul 30, 2016
  • Stayed: Jul 2016
  • Source: HomeAway
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Good Place Stay in Chicago on a Budget

  • 4 of 5

This was a comfortable apartment for our family of 5 during our 5-day stay in Chicago. The apartment is located in a quiet, safe neighborhood and is convenient to CTA buses and several metro lines, particularly the Red Line. The owner is very communicative and had many helpful suggestions to make our visit to Chicago more enjoyable.

The apartment was clean and as described. Also, the owners do a great job of providing plenty of information about the use of the apartment, the local neighborhood and the city and there is plenty of current literature about the city's attractions available at the apartment. The apartment has a pretty good layout with a door that can be closed off between the front bedrooms and the back bedroom and kitchen area. This is a nice feature for early risers who don't want to disturb the slumber is others. The bedrooms are a bit small and the apartment furniture is a bit worn, but nothing to worry too much over.

The best feature of the partner is a terrific roof deck which we enjoyed immensely. Warning however, the deck is accessed by a ship's ladder so it could present a challenge for the elderly or those with limited mobility. The back yard is really a small patio with a good picnic table and gas grill, but it serves it's purposes well. The kitchen appliances are of good quality and in good repair though we did have an issue with the dishwasher leaving a film on the clean dishes. We didn't use the spa but it looked clean and was very large. The bathroom shower was great.

A final "note" which we found a bit odd - there are hand-written notes on 3x5 index cards taped up throughout the apartment with reminders and admonitions to guests to do or not do certain things. We've not run across such notes at other VRBO or Homeaway properties. I didn't mind them but my wife felt like the notes were a bit obtrusive.

All in all, this apartment is a very good value and I would recommend it to others who need the space and don't mind staying a bit away from the city center.

  • Submitted: Jul 11, 2016
  • Stayed: Jul 2016
  • Source: HomeAway
Owner's Response: Thanks for your nice comments Mike, we're glad that you had a great time. Sorry for all of the notes, our property manager does go a bit overboard. It can be a major problem for our next guests when someone walks off with the garage door remote or the parking passes, or when guests leave our front door unlocked when they leave. These things and others happen often enough that we have to put reminders up.
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San Jose, CA

Perfect home base for families

  • 5 of 5

This home is great for families. There is plenty of room to spread out with a full kitchen that we used for breakfasts and occasional dinners in. The location is in the Bridgeport neighborhood right off I-90 @ Pershing exit; very close to the White Sox stadium. This location is a great home base for exploring Chicago. Depending on traffic, it's about 10-20 mins drive to Chinatown, 15-30 mins to Millennium Park area, 20 mins to The University of Chicago and UIC. Having the garage for parking is a bonus & we didn't have problems finding street parking in front of the house. It was very quiet in the evenings and we also felt very safe in this neighborhood.

For an over 100 year old house, it is kept in pretty good shape. To set expectations, the furnishings are dated & you can hear the creaking wooden floors within the unit as well as from guests in the upstairs unit. Weather was fluctuating while we were in Chicago; one day was 70 degrees and raining, and the next day was 90 degrees & humid. Not to worry, the central A/C worked very well on those sweltering days. The favorite part of the unit were the shower jets with plenty of hot water and pressure. We also got to see fireworks from the rooftop deck one evening after the White Sox game. The owners are very responsive, professional & easy to work with.

  • Submitted: Jun 20, 2016
  • Stayed: Jun 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thanks so much for your very nice comments.
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Nearest Airport
7 Miles
Nearest Barpub
0.25 Miles
Shinnick's Bar
Nearest Golf
8 Miles
Harborside or Marovitz
Nearest Train
0.5 Miles
CTA Red Line subway train
Nearest Motorway
0.5 Miles
Interstate 94
Nearest Restaurant
0.3 Miles
Schallers Pump
Nearest Beach
3 Miles
31st Street Beach
Car: not necessary

The map in this ad can be zoomed in or out to different levels so that you can 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.

The Go Chicago Card

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.

Other Activities: Boating, racquetball, basketball

Golf: We have some stellar golf courses here. We'll be glad to recommend a course to fit your needs and skill level. We have everything from 5 star courses that have hosted the U.S. Open to 9 hole municipal courses.


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
FALL 2016
Sep 11 2016 - Oct 20 2016
3 night minimum stay
Fall 2016
Oct 21 2016 - Nov 20 2016
4 night minimum stay
Nov 21 2016 - Nov 24 2016
4 night minimum stay
Nov 25 2016 - Dec 5 2016
5 night minimum stay
December 2016
Dec 6 2016 - Dec 20 2016
3 night minimum stay
2016 Holidays
Dec 21 2016 - Dec 28 2016
5 night minimum stay
New Years Eve
Dec 29 2016 - Jan 2 2017
4 night minimum stay
Jan 3 2017 - Feb 28 2017
3 night minimum stay
Mar 1 2017 - Dec 31 2017
5 night minimum stay
Winter 2018
Jan 1 2018 - Feb 28 2018
5 night minimum stay
My Standard Rate
4 night minimum stay

Additional information about rental rates

Refundable damage deposit $200

If this apartment is taken for your dates, we have another apartment listed on Homeaway and VRBO that is in the same building. Ours is a 2 unit apartment building. The listing number is 271945

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 1
  • Guests provide their own meals
Floor Area:
  • 1300 sq. ft.
Location Type:
  • Monument View ...
  • Town ...
  • Budget
  • Family
  • Activities Guide
  • Air Conditioning ...
  • Alarm Clock
  • Basic Soaps
  • Clothes Dryer ...
  • Fireplace ...
  • Garage ...
  • Hair Dryer
  • Heating ...
  • Internet
  • Iron & Board
  • Laundry Soap
  • Linens Provided ...
  • Local Maps
  • Local Restaurant Guide
  • Parking ...
  • Telephone ...
  • Toilet Paper
  • Towels Provided ...
  • Washing Machine ...
  • Wireless Internet ...
  • Coffee Grinder
  • Coffee Maker
  • Cooking Utensils ...
  • Dishes & Utensils ...
  • Dishwasher ...
  • Ice Maker
  • Kitchen ...
  • Lobster Pot
  • Microwave ...
  • Oven ...
  • Refrigerator ...
  • Stove ...
  • Stove
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 6 people
  • 1 Bathroom
  • 1 Half Bath
  • Bathroom 1 - toilet , shower , Huge 5 x 3.5 ft with Body Sprays
    Bathroom 2 - toilet , In basement and shared between both apartments as a backup
  • 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. The bathroom is done in marble with heated floors. There is an additional half bath in our basement that is shared by both apartments as a backup
  • 3 Bedrooms, Sleeps 6
  • Bedroom 1 - 1 queen
    Bedroom 2 - 1 queen
    Bedroom 3 - 1 queen , 1 sleep sofa /futon , Serta Inner Spring Futon mattress. It's very comfortable.
  • We also have an air bed in the apartment that can be set up in the main living space to create an extra bed in a pinch.
  • Audio Tape Player
  • CD Player
  • DVD Player
  • Radio
  • Satellite / Cable ...
  • Stereo ...
  • Television ...
  • VCR
  • Video Library ...
  • Deck / Patio ...
  • Outdoor Grill ...
  • Outdoor Grill Gas
  • Patio
  • Wood Deck
  • 6 garden chairs
  • Long-term Renters Welcome
  • Low Allergen Environment
  • Minimum Age Limit for Renters ...
  • children welcome ...
  • non smoking only ...
  • pets not allowed
Pool / Spa:
  • Hot Tub
  • Indoor Hot Tub
  • Sauna ...
  • Shared Hot Tub ...
  • Steam Shower
  • churches
  • cinemas
  • library
  • live theater
  • museums
  • playground
  • restaurants
  • zoo
Leisure Activities:
  • antiquing
  • boating
  • gambling casinos
  • outlet shopping
  • shopping
  • sight seeing
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • fishing
  • freshwater fishing
  • golf
  • hiking
  • racquetball
  • roller blading
  • sailing
  • swimming
  • tennis
The guest renting the apartment must be 25 years of age or older. If the guests are under 30, we expect very responsible adults. Our rentals are not a good fit for very hard partiers and very late nights. We don't rent our apartments for parties or gatherings of any kind. Noise late at night or excessive noise anytime is very disturbing to our neighbors and other guests, so our rentals are really not a good fit for the very late night or very hard partying expect a quiet environment crowd. 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 our prior approval only.

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