Chicago,with almost 3 million people, is one of the largest cities in the country. It is situated at the southwest edge of Lake Michigan and thus has a waterfront rivaling that of any coastal city. There are, in fact, 26 miles of lakefront in Chicago. Chicago also has a large suburban area with a vast amount of things to do while visiting with your dog. But the center of a dog-friendly vacation to Chicago will almost certainly be the city, and the downtown area. Chicago is a dog-friendly city and has occupied various rankings in DogFriendly.com's Top Ten Cities in the United States over the years. Things (and rules) are always changing here and thus Chicago has ranked as high as number one and has also fallen out of our Top 10 as well. Right now, Chicago is on an upswing having recently re-opened up patio restaurant dining to pet owners. Surrounding Chicago are the sprawling suburbs which you can read about at these links: North Suburbs, West Suburbs, South Suburbs.
Chicago has no shortage of pet-friendly hotels. Some of the best, with packages for your dog including doggy room service, doggy dining, beds and toys include the The James Chicago, The Allegro, Palomar and Monaco (Kimpton Hotels), the Sheraton Chicago and many more to choose from. These hotels will also find you a pet sitter if one is required. If you are in need of an extended stay pet-friendly hotel there are two Residence Inn's in the downtown. There are also some pet-friendly vacation rentals to stay at.
Doggy dining is now officially "legal" and sanctioned by the city, provided the restaurant files for a petmit to allow dogs at outdoor tables. Many fine Chicago establishments have had doggy dining for years, however, and when it became an issue at some restaurants with the health deparrtment the practice was officially written into statute. If your dog wants to choose from a doggy menu then the Scoozi, with Pizza and Italian food, on 410 W Huron Street is her choice. Other dog-friendly patios are Chicago Joe's, O'Donavan's and many other patios throughout the city. The suburban cities have followed the city's lead and also offer patio dog-friendly dining.
If shopping is your dog's true love, then you can do worse than a trip to Chicago. Many stores in Chicago will allow you to carry a small dog or walk with a well-behaved leashed dog while shopping. The Geneva Commons Shopping Center in suburban Geneva is a great dog-friendly open-air shopping mall. Also dog-friendly are the Historic Long Grove Shopping District. Many of the larger stores on the Magnificent Mile (Michigan Avenue) in downtown Chicago will also let a small dog or a well-behaved, leashed dog shop. And the Shops at North Bridge on Michigan Avenue is also dog-friendly.
Chicago has many off-leash dog parks but they are difficult for visiting dogs to use. They require that you get a permit which requires payment, proof of quite a few vaccines and this usually gets handled through local vets. Quite a lot to do if your visiting for a few days. If you do get the permit, then the many off-leash parks in the city are open to you as well as the Montrose Harbor Dog Beach, the only Lake Michigan Dog Beach within the city. There is also an Evanston Dog Beach in the city of Evanston but it also requires you to get a permit, this one from Evanston. There is a small beach at Belmont Harbor where dogs are allowed but must be leashed. Off-leash dogs here can and will be ticketed.
The real attraction of Chicago for visitors lies in the things to do for visitors in Chicago. The summer in Chicago brings Mercury Canine Cruises, a Sunday dog cruise on Lake Michigan. Not there on Sunday? All of there tourist cruises also allow your leashed dog. Also dog-friendly boat cruises are the Seadog Cruises at Navy Pier and Shoreline Sightseeing Boats. Walk with your dog in Grant Park and view Buckingham Fountain or take a carriage ride with your dog. In Evanston you can walk your dog through the Ladd Arboretum which is 23 acres in size. The Navy Pier, with rides for the kids, food stands and shops is leash friendly. The Chiago White Sox have an annual dog day at the baseball park. Outside of town you can walk your dog on the grounds of the Fermi National Accelerator Lab, but they aren't allowed in buildings. There are concerts in the park at Lincoln Park in St Charles and take your leashed dog to the Illinois Railway Museum in Union. Six Flags doesn't allow dogs but does have a dog kennel.
Chicago is one city where you can do many of the things that you would want to do as a tourist with your dog in tow. For the theatre or some nightlife options a pet sitter may be required but for many activities you may take your dog.