Hotel Home Base:
the James Hotel Chicago, they have become our go-to dog-friendly hotel. The gladly accepts all sizes and breeds of dogs and the staff is beyond friendly always giving the pups a friendly pat and running to grab the door for us. They provide dog beds and food bowls. The hotel is also in a really convenient location near north Michigan Avenue across from the Trader Joe's (perfect for picking up extra dog treats, people snacks, and inexpensive late-night bottles of wine). It's also near Chicago Avenue which is the entrance to the lakefront path and within short walking distance to all the activities described below so you can always make quick trips back to rest at the hotel.
Morning Walk to Navy Pier:
You can pick up an (overpriced!) Chicago hot dog from a cart and check out some of the best skyline views in the city. See more of what our pups did at Navy Pier here, including a video from Mr' B's camera.
After spending the morning at Navy Pier, take the lakefront path back towards your hotel. The lakefront spans over 18 miles passing along several neighborhoods along with skyline views. If the weather is nice out, you can even plan for this.
Portillio's for the best Chicago-style hotdogs, or M Burger . Knowing how dangerous it can be to leave our dogs outside a store unattended, one of us always stays with the dogs while the other picks up food. (We wrote more about it here).
Or it's always fun to stay in the hotel with movies and room service.
Ghirardelli's for some caramel salted hot chocolate or ice-cream and check a less crowded Michigan Avenue. If your pups are interested in meeting people, walk by the Rush and Division street area. At night the area is known for drunken debauchery; someone even tried to grab Miss M's tush when she was walking there!
We also wrote more about nighttime adventures, here.
These are our recommendations for a 1-night downtown stay with your pups.
What would be your favorite part? And any locals have any other must-see's?
What we learned about staying in a hotel with dogs.
If you had a second day...
Winter (with hats!)
We always love these staycation ideas