1. The Chicago Dog Devotee
CHECKLIST: There are Chicago dogs (i.e. no ketchup), and then there are Chicago dogs, the four-legged variety. The Windy City is perennially a top pick in terms of canine-friendliness, and why not given the variety of places for you and the pooch to live. You’ll be taking a lot of walks, so you won’t want to tackle too many stairs. It would be nice to have some boutiques nearby, but a coffee shop to get your morning caffeine is non-negotiable. You’d love a leafy neighborhood with a quieter feel, and of course some dog park nearby.
CONSIDER: A duplex-down in a newer three-flat or six-flat
WHERE: Bucktown/Wicker Park, Humboldt Park, North Center, Bronzeville
ON THE MARKET: 2606 W. Thomas Street #1
You won’t have to spend time remodeling before moving into this Humboldt Park three-bedroom. There are plenty of play spaces in the sunroom and family room for pets to roam. Grill on the deck in August and use the backyard for reluctant pooches on those freezing February mornings. Maintain your cool cred (and get some of the city’s best java) at nearby Dark Matter. You’re walking distance to Humboldt Park, with numerous doggie day care and pet spa options in the neighborhood.
2. Fresh From the Suburbs
CHECKLIST: You moved to the city to get closer to the action, so you’re looking for a heavy dose of social life and all the culture Chicago has to offer. You want proximity to the buzziest restaurants, trendy boutiques, and acclaimed museums and galleries. You’re ready to savor some great skyline and lakefront views, and you also need parking for your beloved car.
CONSIDER: A high-rise or mid-rise condo with garage parking
WHERE: Streeterville, River North
ON THE MARKET: 270 E. Pearson Street #303
This condo on the Near North Side puts you in the center of it all, with Lake Michigan, the world-class Museum of Contemporary Art, Mag Mile shopping and great restaurants nearby. This condominium features many of the comforts you enjoyed in your suburban home, including a fireplace, a spacious primary suite and treeline views from a private balcony. You’ll also find city amenities like an onsite fitness center, 24-hour security and a dry cleaner. Not only is there a deeded parking spot for your car but there’s also an assigned storage unit for all your mementos and treasures.
3. The Luxury Maven
CHECKLIST: You’ve worked hard for your success and make no bones about enjoying the rewards. The word ‘compromise’ is not in your vocabulary. You’re accustomed to the finest in fashion, cars, and travel, and your living space needs to be just as refined as your tastes.
CONSIDER: Penthouse
WHERE: Gold Coast, Lincoln Park, West Loop
ON THE MARKET: 500 W. Superior Street #2703
The bespoke architectural details in this three-story penthouse on the Near North Side create a one-of-a-kind residential work of art. The building was designed by famed Japanese-American architect Minori Yamasaki and converted from office to residential use in the early 2000s. The developer hired Chicago-based interior designer Darcy Bonner to customize the top floors for his own residence and spared no expense. A mix of glass, granite, metal and a variety of woods create a rich palate that is cool and modern in some rooms and warm and inviting in others. From the private elevator, to the glass architectural staircase, the stunning views, sleek chef’s kitchen and wine room, this condominium has all the high-end features you’d expect in the ultra-luxe market.
4. The Power Commuter
CHECKLIST: Unlike the newly-ex-suburbanite, you’ve ditched your four-wheeled transportation and are completely comfortable relying on Chicago’s excellent mass transit for the foreseeable future. You’re a pro at using the L, buses, Divvy bikes, Metra and rideshares to get wherever you need to go – whether that’s the office, restaurants, the ballpark, O’Hare, Midway, and even the ‘burbs. Easy access to groceries, the gym and other conveniences is important, and the beauty of Chicago is that any number of neighborhoods gives you all of the above.
CONSIDER: Low- or mid-rise condo near the L
WHERE: Ravenswood, Logan Square
ON THE MARKET: 4802 N. Bell Avenue #504
This newer construction, Lincoln Square condo puts you right in the middle of everything you’ll need, with convenient access to both the Metra and L, as well as grocery stores, gyms and Winnemac Park. Inside, it’s perfectly appointed with 10’ ceilings, a wine fridge, gas fireplace with decorative-tiled full-height surround, and a roomy, upscale kitchen. You’ll also have private access to the rooftop deck, which has its own fireplace, a gas line for grilling and surround sound speakers.
5. The Triathlete
CHECKLIST: The person running along the lakefront at 5 AM, in 10-degree-below weather, guided by a flashlight strapped to their head…that’s you! No matter the conditions, the time of year, or the hour of day, you’re training for your next big race, and your choice of home needs to support your lifestyle. The city is your exercise room, so your condominium must be a convenient running or cycling distance from the lakefront. An inspiring view is a plus to enjoy your pre-workout bulletproof coffee.
CONSIDER: Walkup or secure building with bike storage
WHERE: Edgewater, Andersonville, South Loop, Lakeview
ON THE MARKET: 1211 S. Prairie Avenue #706
In this Near South Side condo, you’ll have no excuse for skipping a training day—not that you need one. There’s a soaking tub in your bathroom for recovering from post-run soreness and heated floors to keep you comfy even in the chilliest of mornings. You’re steps from the lake, the Field Museum and all the running and biking paths you’d ever want. But, should you ever get the urge to move your workout indoors, there’s also a sauna, sundeck, fitness center and an indoor and outdoor pool in the building. Check, check, check and check.