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Book Online or call HomeAway Booking Assistance +44 (0) 800 917 5992

Large 3 BR Apt. for Families and Groups. Close to EVERYTHING. City Skyline View.

Bedrooms 3
Separate WC's1
Space 1,275 sq ft
Property type apartment
Minimum Stay 4 - 5 nights


About the property

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

__ Large Comfortable Apartment that You will Love.

Families and large groups love our rentals. The apartment has 3 bedrooms and sleeps up to 6 persons in 3 Comfortable Queen Beds. We also have a queen air bed in the apartment.

__ A REAL 15 Minutes to Everything that is Chicago.

__ 10 Minutes to McCormick Place.

__ Amazing Skyline View from our seasonal deck.

10 years of all 4 and 5 Star Reviews.

Our Area:

__ Voted Safest Area in Chicago by Zillow for trick or treating. A quiet, historic and friendly, neighborhood. Our home for 28 years.

__ Why were we voted Safest? More high ranking Police and other city officials live in our area than any other.

__ Huge 5 Star Hot Tub. Garage parking included with your rental.

__ Eat Real Chicago Food and save big $$$ Eating Locally or enjoy our world famous 5 star restaurants.

Our Location:

_ Located on the near South Side in the safe and quiet area of Bridgeport. We chose this area to live ourselves out of the entire city.

__ A Real15 minutes to Navy Pier, Millennium Park,our Theater District, Bears games. 1 minute to White Sox Games and train direct to Wrigley Field for Cubs games.

__ One Click and Uber and Lyft get you everywhere. They arrive in minutes.

__ You won't believe how much there is to do here. We'll send you a list of hundreds of our best attractions in our extensive guest guide to the city and our area. Email us, and we'll send it whether you stay with us or not.

Your Apartment:

__ Full Kitchen with everything that you will need to cook.

__ Amazing 5 Foot by 3.5 Foot Steambath Shower with Grohe Body Sprays. See the Picture. Guests Say They Are Like a Massage

__ 65 Inch TV. HUGE and comfortable entertainment/ living room.

__ Large Dining Room table and 4 Person kitchen table.

__ 2nd Apartment Available. You can rent the entire building.

Our Building:

__ Huge 5 Star Hot Tub

__ Amazing Skyline View from our seasonal deck.

__ All Great Places to Relax after a Long Day.

__ Patio with Picnic Table and Gas Grill.

__ Garage Parking Space Included.

__ 2 Washing Machines and 2 Dryers.

__ Apartment is not ADA accessible.

There are 3 full separate bedrooms, each with a comfortable queen bed.

House Rules:

__ No Parties or Gatherings.

__ No Loud Noise Late at Night

__ Not a good fit for very hard partiers and 2-4 am people.

__ We do not rent for Music Festivals or Concerts. A few irresponsible groups ruined that for everyone.

__ We rent to responsible adults over 23 only.

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

More Details
Registration Number : 2074660

Bob Groble and Bob Condon
Member since: 2007
Premier Partner

This partner has demonstrated and is committed to fast response times, the best rates, and a great guest experience.

Speaks English
Response time:
Within an hour
Response rate:
Calendar last updated:
20 May, 2018

About Bob Groble and Bob Condon

We are two lifelong friends who bought this building to live in. We remodeled it completely for ourselves with 5 star extras, and later converted it to a vacation rental.

Bob Groble and Bob Condon purchased this apartment in 2000

Why Bob Groble and Bob Condon chose Bridgeport

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 a real 15 minutes away. 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

My family of four (parents plus two pre-teen daughters) stayed at Bob's place for a week during spring break. We were able to enjoy the comfort and privacy of a home that provides luxury amenities and do all the sightseeing (museums, zoos, aquarium, Sky Deck, Navy Pier, Blue Man Group) we wanted without breaking the bank - and we still had an extra bedroom! The things we enjoyed most about Bob's place: 1) hot tub, 2) rooftop deck, 3) luxury shower, 4) well equipped kitchen, 5) local neighborhood restaurants (we recommend Kathy's for breakfast sandwiches and Rico Bene's for delivery Italian & great Chicago hotdogs!), 6) convenience of location to highway and downtown (we could get everywhere we wanted to go in 10-20 mins), 7) garage parking. When you stay at Bob's place, he provides you with a ton of very thorough pre-trip information and tips that will help you get the most out of your experience while being cost conscious. More...

· By Lisa from Indianapolis, IN on 4/7/2010 for a stay in 3/2010
Mar 2010
  • 1 of 19


Accommodation and facilities for this holiday apartment in Bridgeport in Chicago

Property Type:
  • apartment
  • floor 1
Building Type:
  • building
  • Self-catering
Floor Area:
  • 1275 sq ft
House Rules:
  • Check-in: 15:00
  • /
  • Check-out: 10:00
  • Max. occupancy: 6
  • Min. age of primary renter: 23 ...
  • Children welcome ...
  • Parties/events allowed ...
  • Pets not allowed
  • Non smoking only ...
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 ...
  • Hob ...
  • Stove
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 6 people
  • 1 Bathroom
  • 1 Separate WC
  • Bathroom 1 - Toilet , Shower Enclosure , 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 Large Double Bed
    Bedroom 2 - 1 Large Double Bed
    Bedroom 3 - 1 Large Double Bed , 1 Sofa bed/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.
  • DVD Player
  • Satellite / Cable ...
  • Television ...
  • Terrace ...
  • Barbecue ...
  • Outdoor Grill Gas
  • Patio
  • Wood Decking
  • 6 garden chairs
  • Long-term Renters Welcome
  • Low Allergen Environment
  • wheelchair inaccessible ...
Pool / Spa:
  • Hot Tub
  • Indoor Hot Tub
  • Sauna ...
  • Shared Hot Tub ...
  • Steam Shower
  • churches
  • cinemas
  • library
  • live theatre
  • museums
  • playground
  • restaurants
  • zoo
Leisure Activities:
  • antique hunting
  • Boating
  • gambling casinos
  • outlet shopping
  • Shopping
  • sight seeing
Local Services & Businesses:
  • ATM/bank
  • fitness centre
  • 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.


Wonderful! 4.9/5 -
(97 traveller reviews)

86% Complete
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Large 3 BR Apt. for Families and Groups. Close to EVERYTHING. City Skyline View.
average rating of 4.865979 based on 116 reviews

Lots of room, clean and close to the Red Line

  • 5 of 5

We are 3 women in our mid-sixties in Chicago for opera and fun. In spite of warnings about safety while staying on the South Side we never felt the slightest unsafe. The apartment is clean and comfortable not fancy. It is an easy 15 minute walk to the Sox-35 L station that gets you downtown in 15 minutes. Good value for close in Chicago. Grocery stores are sparse. CVS is. a one mile walk and carries most necessities. Be sure to enjoy breakfast at Nanna’s, near CVS.

  • Review Submitted: 23-Apr-2018
  • Date of Stay: April 2018
  • Source: VRBO, from HomeAway
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Great place for our family of four

  • 4 of 5

As our teenage kids said, "This was so much better than staying in a hotel!" They each had their own room, as did my husband and I. The hot tub was a real treat every evening. We enjoyed the huge TV and the dining table in the sunny bay window. The location was convenient to the central city, and we could walk 15 minutes to catch the train. A garage in which to park our car was a plus, too. We had a great stay!

  • Review Submitted: 31-Mar-2018
  • Date of Stay: March 2018
  • Source: VRBO, from HomeAway
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Comfortable Bridgeport Area in Chicago Apartment

  • 4 of 5

Liked the hot tub, great wifi, and secure covered garage for parking.

  • Review Submitted: 21-Mar-2018
  • Date of Stay: March 2018
  • Source: VRBO, from HomeAway
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Perfect location for business at McCormick Place

  • 5 of 5

This was our second stay at this location. It is a great place to come back to after a long day at McCormick Place which is only a $15.00 Uber ride away. The neighborhood is nice and the deli right around the corner has wonderful food. Bob responded quickly to any questions we had. We look forward to coming back for our next tradeshow in Chicago.

  • Review Submitted: 05-Feb-2018
  • Date of Stay: January 2018
  • Source: VRBO, from HomeAway
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Very clean and comfortable.

  • 5 of 5

We had a wonderful weekend rendevous of three sisters and our three daughters. We had no problems or issues. We would stay here again if needing a place in Chicago. Thanks Bob and Bob for your hospitality.

  • Review Submitted: 27-Jan-2018
  • Date of Stay: January 2018
  • Source: HomeAway
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Andover, MN

Cozy clean get away. This has it all!

  • 5 of 5

I recently spent a nice quiet weekend visiting family in Chicago and stayed in this very relaxing home. The owner responded quickly to any questions I had and provided excellent instructions. We were close to train connections into Chicago and felt very comfortable while we were here. The hot tub on the back porch, the large TV and main level deluxe steam shower were an added plus. I would absolutely stay here again particularly in warmer weather in order to enjoy the rooftop deck with a view of the city skyline!

  • Review Submitted: 22-Nov-2017
  • Date of Stay: November 2017
  • Source: VRBO, from HomeAway
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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.


Prices & Availability

Ask Owner a Question

Additional pricing information

Damage Deposit £148.52

Ours is a 2 unit building. 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. Our other apartment is HomeAway listing number 271945

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.

Owner's Cancellation Policy

  • 50% refund for cancellations more than 30 days before check-in date.
  • 100% refund for cancellations more than 60 days before check-in date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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