Chicago is one of the most dog-friendly cities in the country, so it's a real treat to visit with your pooch. This is especially true in the summer months, when you can take full advantage of the city's many parks and lakefront area.
For a fun day in the sun, head to Grant Park to get your picture taken in front of Buckingham Fountain, then head across the street to the Lakefront Trail. Follow it north for about a mile and you'll reach Navy Pier. This Chicago landmark is home to a 50-acre park, and dozens of shops, restaurants and attractions. The Ferris wheel and other rides are off limits to dogs, but they are allowed in most outdoor areas and food court tables. As tempting as that may be, we suggest getting an authentic Chicago-style pizza at Pizzeria Uno instead. It's just one mile away from Navy Pier (on the corner of E. Ohio & N. Wabash) and has five outside patio tables for you and the pup-peroni.
But since the four seasons in Chicago are winter, winter, winter, and the Fourth of July, you might not want to count on outdoor activities entirely. Luckily, the number of indoor attractions in Chicago is plentiful as well, at least for humans. You could easily spend an entire day at the Art Institute of Chicago, or hop from museum to museum at Grant Park. Once they're all closed, head to Second City to laugh your you-know-what off at an improv show, or have a cocktail at the Green Mill, where the smoky sounds of jazz will fill the room 'til the wee hours of the night. Er, morning.
When you bring your dog to Chicago, you should definitely set a couple of hours aside for Mercury Skyline Cruiseline's Canine Cruise. Their 90-minute boat tour includes lively commentary on local architectural and historical points of interest, as well as dog parks, outdoor restaurants, and other pet-friendly establishments. Food isn't served on the tour, but there are water bowls on board as well as a newspaper-lined restroom.
The Canine Cruise is offered on Sundays only from July through September. Tickets are $18 for adults, $8 for kids under 12, and $5 for dogs. The boat departs at 10am, but you should arrive at least half an hour early to get a seat. You'll find the boat and ticket office on the Riverside Gardens Dock, at the corner of Michigan Avenue and Wacker Drive. Look for the blue awning! Call 312-332-1353 for more information.
If you won't be in town on a Sunday, try Shoreline Sightseeing's Architecture Cruise instead. Tickets are a little more expensive, but tours depart from Navy Pier several times a day (May-October) and dogs are allowed on board.
