Buying a Second Home in Chicago – Chicago Pied-a-terre

“What do I need to know about buying a second home in Chicago?” We are seeing a large number of buyers enter the market to purchase a second home in Chicago. Many of these buyers live in the suburbs of Chicago and are purchasing a condo in the city to enjoy on the weekends (or during the week if they work late) but also for investment. With interest rates at or below 4% and condo prices still at record lows many suburban buyers are entering the market. But what do you need to know about buying a second home in Chicago?

Location: We’ve all heard the old saying “Location, Location, Location” and it is very true. It is even more relevant if you’re buying a second home in the city because you will likely not be spending much time in your home as you may be dining out, seeing shows, enjoying summer events, etc. Buy a location that you’re going to love. If you are always at Millennium Park for free concerts start your search in Lake Shore East. If you have a boat at Burnham Harbor then start in the South Loop. Above I mentioned that many who purchase second homes are also looking at the purchase as an investment. While there are certain areas of the city that may be better investments than others, good deals can be found in any neighborhood. It is important that you’re going to enjoy the location to the fullest.

Doorman Building: If you’re buying an “in town” I typically recommend you purchase a condo in a building with a doorman. Since you won’t be at your unit 24/7 it is comforting to know that if you forgot to turn your heat on or need your unit check on someone is there to do it. It also helps if you have someone coming into town and you want to allow them to use your condo for the weekend. A doorman can give keys to your children, friends, family, etc. if you give permission.

Understand What you can and can’t do with your unit: Rental restrictions in buildings have increased over the years. For multiple reasons that I won’t get into now, some condo associations limit your ability to rent out your unit. If you never ever plan to rent your unit then no worries. However, if one of your investment strategies or future plans may be to rent the unit then you will want to pay particular attention to whether or not the building you are buying into allows rentals.

Understand your future needs: I’ve had some second home buyers look only at 1 Bedroom condos at first but then they started to think about eventually using the condo full time. With this being said it is important to fully understand your future needs for the condo. Do you plan to eventually move into the unit full time? If so, how much space will you need and want?

Walk-ability: This fits in to “Location, Location, Location” but pick a location where you can easily walk to things such as a grocery store, restaurants, etc. If you’re using the condo as a second home then it should feel like you’re on vacation when you’re using it. You want as much at your finger tips as possible.

What are the best areas to buy a second home in? This all depends on your personality. What areas of the city do you like the best? My experience with clients has been that Streeterville, Gold Coast, (east) River North, and Lake Shore East have been the most popular areas to search for a second home. All these areas offer inexpensive options as well as some of the most luxurious in the city.

Paul Blackburn is an Illinois Licensed Realtor and Broker with @ Properties in Chicago. He can always be reached via e-mail at


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