Skip to main

    385 Prince of Wales Drive & 383 Prince of Wales Drive


    Highlights

    Property Type:
    Condo
    Number of Storeys:
    36
    Number of Units:
    484
    Condo Completion:
    2010
    Condo Demand:
    Medium
    Unit Size Range:
    394 - 1,800 SQFT
    Unit Availability:
    High
    Property Management:

    Amenities

    BBQs Allowed
    Indoor Parking
    Party Room
    Indoor Pool
    Gym
    Concierge
    Visitor Parking
    Rooftop Deck
    Amenity details for reference only. Independently verify accuracy.

    About 385 Prince of Wales DriveChicago Condos

    Regardless of what the name implies, the Chicago Condos is certainly not located south of the border, in the windy city. Instead, this modern Canadian condominium can be found at 385 Prince of Wales Drive and 383 Prince of Wales Drive in Mississauga.

    Daniels Corporation is responsible for the creation of the Chicago Condos, and the tower comprised the developer’s 6th building in its master-planned City Centre Community. Kirkor Architects Planners designed the 36-storey residential edifice, and construction was completed in 2010.

    In addition to 484 homes, over 17,000 square feet is dedicated to amenities. Residents have access to a gym, indoor pool, sauna, party room, theatre, games room, rock-climbing wall, virtual golf, and terrace with barbecue and dining area — plus the building is equipped with a concierge and underground parking.

    The Suites

    The homes at 385 Prince of Wales Drive range dramatically in terms of size and layout: Suites start at approximately 450 and reach to around 6,000 square feet, and consist of anything from studios to three bedroom plus den units. Style-wise, however, the homes throughout the building feel rather consistent, thanks to thoughtful interior design details by Hudson Kruse.

    The Neighbourhood

    Planned with active residents in mind, the Chicago Condos is situated in Mississauga’s most exciting neighbourhood: the Downtown Core. Those living in the building can walk just a few short blocks in order to reach local attractions like the Cineplex Cinemas Mississauga, the Living Arts Centre, the Art Gallery of Mississauga, and Square One Shopping Centre. And when it comes time to stock up on groceries, residents at 385 Prince of Wales Drive can choose between grabbing organic goods from Whole Foods or exploring the Asian imports at T&T Supermarket.

    Transportation

    With bus stops right outside the front door of 385 Prince of Wales, even residents who prefer not to drive can get around the city with ease. The 20 Rathburn and 26 Burmanthorpe buses come in handy for those hoping to connect onto the TTC subway system, as both of these buses carry passengers to Islington Station on the Bloor-Danforth line. Drivers, on the other hand, can make use of nearby highways like the 403, the 401, and the QEW.

    Water
    Included
    Hydro
    Not Included
    Heat
    Not Included
    Air Conditioning
    Not Included

    Listing History for Chicago Condos

    Nov, 2025
    385 Prince Of Wales Dr, unit 416 for sale
    Unit 416
    Nov 20, 202593 days on strata
    ExpiredListed for $529,8881 bd + 1 | 1 ba | 657 sqft | 1 pkg
    385 Prince of Wales Dr, unit 1605 for rent
    Unit 1605
    Nov 11, 202539 days on strata
    Leased for $2,350Listed for $2,5501 bd + 1 | 2 ba | 709 sqft | 1 pkg
    Receive listing updates for Downtown Core

    Reviews for Chicago Condos

    Daphne R
    January 21 2025
    5 out of 5
    I've lived in this condo for many years and it's managed wonderfully.
    Sophie Rodrigues
    April 1 2025
    Owner
    5 out of 5
    I have to give credit to management, they are so fast to answer my emails and calls - I feel like a priority.
    M. Johnson
    April 7 2025
    5 out of 5
    Rented here for many years and its aged well. Staff are wonderful. It's a great place to live!
    Roman H
    April 16 2025
    Owner
    5 out of 5
    Proud original owner at Chicago Condominiums. Great building with helpful staff. Management ensures it stays safe and well-managed.
    Jamal
    April 21 2025
    5 out of 5
    The staff at this building is exceptional—professional, friendly, and attentive. The property is always clean and well-maintained.
    Daniel Peterson
    June 10 2025
    5 out of 5
    Wish I could give more stars. The staff at this building is professional, attentive, and always available to help, making residents feel like family and building a real community at Chicago.
    7

    Listings For Sale

    Interested in receiving new listings for sale?

    7

    Listings For Rent

    Interested in receiving new listings for rent?

    Similar Condos

    Explore Downtown Core

    Map

    © OpenStreetMap
    map of location
    View My Travel Time
    9/10
    Walkability
    One small step for you. One giant leap towards never needing a gym membership.
    8/10
    Transit
    So frequent, you might accidentally start collecting tickets.
    5/10
    Bikeability
    A perfect balance of challenge and 'Hey, I didn’t know there was a bike shop here!'

    Demographics

    Based on the dissemination area as defined by Statistics Canada. A dissemination area contains, on average, approximately 200 – 400 households.

    Population
    9,194
    Average Individual Income
    $63,586
    Average Household Size
    2 persons
    Average Age
    60
    Average Household Income
    $105,144
    Dominant Housing Type
    Detached
    Population By Age
    0 - 14
    16%
    15 - 19
    1%
    20 - 34
    23%
    35 - 49
    19%
    50 - 64
    21%
    65+
    17%
    Household Income
    $0 - $30,000
    44%
    $30,000+
    28%
    $60,000+
    16%
    $90,000+
    6%
    $125,000+
    3%
    Housing Types & Tenancy
    Detached
    41%
    High Rise Apartment
    24%
    Semi Detached
    24%
    Low Rise Apartment
    6%
    Duplex
    3%
    Marital Status
    Commute
    Languages (Primary Language)
    English
    83%
    Other
    8%
    Punjabi
    4%
    Tagalog
    1%
    Hindi
    1%
    Spanish
    1%
    Mandarin
    1%
    Urdu
    1%
    Education
    High School
    32%
    University and Above
    25%
    College
    21%
    None
    15%
    Apprenticeship
    3%
    University Below Batchelor
    1%
    Major Field of Study
    Business Management
    26%
    Architecture & Engineering
    20%
    Social Sciences
    12%
    Health & Related Fields
    10%
    Math & Computer Sciences
    6%
    Personal, Protective & Transportation Services
    5%
    Humanities
    4%
    Education
    4%
    Physical Sciences
    3%
    Visual & Performing Arts
    3%
    Agriculture & Natural Resources
    1%



    Days on Strata

    Units at Chicago Condos spend an average of
    30
    Days on Strata
    based on recent sales

    List vs Selling Price

    On average, these condos sell for
    1%
    above
    the list price.

    Offer Competition

    Condos in this building have an
    AVERAGE
    chance of receiving
    Multiple Offers
    compared to other buildings in Downtown Core

    Turnover of Units

    On average, each unit is owned for
    5.5
    YEARS before being sold again

    Property Value

    -14%
    Decrease in property value within the past twelve months

    Price Ranking

    13th
    Highest price per SQFT out of 51 condos in the Downtown Core area

    Sold Units

    21
    Units were Sold over the past twelve months

    Rented Units

    89
    Units were Rented over the past twelve months

    Best Value Rank

    Chicago Condos offers the
    ?
    best value out of 51 condos in the Downtown Core neighbourhood

    Appreciation Rank

    Chicago Condos has the
    ?
    highest ROI out of 51 condos in the Downtown Core neighbourhood

    Rental Yield

    Chicago Condos yields the
    ?
    highest rent prices out of 51 condos in the Downtown Core neighbourhood

    High Demand

    Chicago Condos is the
    ?
    most popular building out of 51 condos in the Downtown Core neighbourhood

    Market Insights

    Transaction Insights at Chicago Condos

    Studio1 Bed1 Bed + Den2 Bed2 Bed + Den3 Bed3 Bed + Den
    Price RangeNo Data$430,000 - $496,000$430,000 - $570,000$510,000 - $610,000$665,000No DataNo Data
    Avg. Cost Per SqftNo Data$736$753$664$613No DataNo Data
    Avg. Wait for Unit Availability161 Days28 Days25 Days79 Days148 Days486 Days493 Days
    Ratio of Units in Building6%32%40%11%6%2%5%

    Market Inventory

    Total number of units listed and sold in Downtown Core