Neighborhood · St Petersburg, Florida
Chicago
A quiet St Pete pocket with tight inventory
Chicago is a small residential neighborhood inside St Petersburg, tucked into the Pinellas peninsula between well-known waterfront communities. It sits near Shore Acres and Greater Pinellas Point, with the causeways and bridges that make Tampa a short drive away — the airport (TPA) is about 29 minutes out and Downtown Tampa roughly 31. It's the kind of established, low-key pocket that appeals to buyers who want St Pete access without the crowds.
The market reality here is scarcity: there are currently zero active listings, so this is a neighborhood you buy into when something comes up. Over the last 12 months just five homes sold, at a median price of $587,500, and sellers collected about 98% of their asking price on average. If you're set on Chicago, be ready to move quickly and consider nearby options like Bayway Isles or Disston Heights while you wait.
Chicago is a community in St Petersburg, Florida.
Quick facts
4 sold in 12 months
Drive times
On the market now
Homes for sale in Chicago
Nothing active right now.
Set an alert below and we’ll email you the moment something lists here.
Every active listing inside the Chicago boundary
Open full map search →The numbers that matter
The Chicago market
4
Sold, last 12 months
$653,750
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
73 days
Median time to sell
Chicago vs St Petersburg
Live Stellar MLS data — every listing and closed sale inside the Chicago boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Chicago is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
Population
117
Median age
38
Median income
$89,219
Median home value
$445,100
Beyond the listings
Living in Chicago
Attitudes
Top 3% in the U.S.Volunteering & Giving
Expressing a desire to give back and do good for the community, this behavior emphasizes charity. Common activities include volunteering, fundraisers, and donations.
Hobbies & Interests
Top 6% in the U.S.Bookish
Always seeking the next book, article, or poem to read, this activity is prevalent in areas where reading is a way of life. Although a solo activity, the expression of the love of books is a bonding, communal experience.
Relationships
Top 7% in the U.S.Connected Motherhood
Motherhood is a unique journey for every woman. There are highs, lows,and lots to celebrate. These moms seek to share their experiences and engage with a community of moms.
Relationships
Top 8% in the U.S.Networking
Driven to succeed in the business world, this population seeks to progress in their career through networking happy hours, summits, and connecting with other professionals online.
Hobbies & Interests
Top 9% in the U.S.Animal Advocates
Passionate about animal welfare, this population wants to know how best to care for their own pets (with toys and training) and help other animals find their fur-ever home.
Pieces of History
You can find these people researching an upcoming exhibit at the natural history museum or learning about a famous monument. This population enjoys learning about the past.
People who close here
Our St Petersburg experts
Straight answers
Chicago FAQs
Is Chicago a good place to live?+
It's a small, established residential pocket of St Petersburg with easy reach to Tampa — the airport is about 29 minutes and Downtown Tampa around 31. It's assigned to John Hopkins Middle, Campbell Park Elementary, and Gibbs High School. The appeal is a quieter St Pete address near well-known communities like Shore Acres.
Is Chicago expensive?+
Recent sales point to a solid mid-market price point: the median sold price over the last 12 months was $587,500. There are no active listings at the moment, so pricing on new inventory will depend on what comes up. For comparison shopping, look at nearby Greater Pinellas Point.
What do homes cost in Chicago?+
Over the past year, five homes sold here at a median price of $587,500. With no active listings currently, there's no live list price or price range to quote. That small sample means each sale carries real weight in setting the neighborhood's value.
How is the market in Chicago?+
It's a low-turnover, tight-inventory market — just five homes sold in the last 12 months and zero active right now. Sellers averaged about 98% of asking, which tells you buyers who want in should be ready to act fast. Widening your search to Disston Heights can keep options open.
What about HOA fees and property taxes?+
We don't have current HOA or property tax figures for Chicago in the data, which is common for a small neighborhood with so few recent transactions. Florida property taxes vary with assessed value and homestead status, so budget based on the specific home. Your agent can pull the exact figures once a listing is active.
Keep exploring
More St Petersburg neighborhoods
Neighborhood boundary by edgeAI; listings matched to the polygon. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
Never miss a listing
New Chicago homes, in your inbox
A daily digest of new St Petersburg listings — straight from the MLS. Unsubscribe anytime.