There are plenty of dog-friendly homes and apartments in the area and despite the frigid winter weather, several restaurants boast patios with a relaxed atmosphere that welcome dogs. Whether you're in the mood to try some local microbrews, eat a few authentic Mexican tacos, or sip on a cappuccino, there's likely a patio space you and your four-legged tag-along can enjoy together.
If you feel like escaping the hustle and bustle of the city, head to Lincoln Park, which hosts a number of amenities, including a loop trail that has designated bike and pedestrian paths, keeping your dog safe from any negative interactions with bicyclists. You can even take a series of trails within the 500 acres of Lincoln Park all the way north, even reaching Foster Beach, or south, reaching down to Navy Pier.
The city of Chicago is located on the Chicago Plain, emphasizing its flatness, which eventually recedes into Lake Michigan. It's unlikely a typical walk will leave you huffing and puffing or your pet panting as steep hills are not typical.
Every major metropolitan hub has a spacious, amenity-laden park for its city-dwellers to retreat into. For New York City it's Central, for San Francisco it's Golden Gate, and for Seattle it's Discovery; in Chicago, it's Lincoln Park. Lincoln Park is 500 acres of gardens, open fields, a 150-year-old zoo, and a conservatory. There's even access to the beach from Lincoln Park (however, for dog-friendly beaches, you'll need to head north and visit either Foster or Montrose Beach).
Some details concerning Lincoln Park and its dog-related rules:
Oz Park, named after the infamous book and film, The Wizard of Oz, has a jogging trail through its shady greenery for you and your dog to enjoy. After the exercise, take a much-needed breather and walk around viewing a few statues dedicated to the author, L. Frank Baum, who once lived in the area.
Bauler Playlot Park is a small neighborhood park that's frequented by the young families living in the Lincoln Park neighborhood. There are spacious sidewalks to stroll down and park benches to sit at and enjoy people and dog watching.