Thinking about traveling to the Windy City (aka: Chicago) with your pooch? Well, you are in luck! My humans and I just got back from a visit (January 2019) and I’ve got all the 411 you will need to make your dog-friendly Chicago visit a blast!

Where to Stay:

So, you got to Chicago after flying or driving with your pooch. Now what? Well, now you check in to the most dog-loving hotel you will ever stay in!

The Staypineapple Chicago, An Iconic Hotel, is just steps from Millennium Park, in the heart of downtown Chicago (the Loop). So, the location is pawfect!

This boutique hotel is full of charm, personality and unique little details; for both humans and pups* alike (*dog fees apply). But let’s be real, what we really care about is how they pamper the pups!

In the lobby, you will find a jar of free dog treats as well as a board where they write down the names of the dogs checking in, daily. I mean, how cute is that?!?!?!

In the room, they have dog bowls, poopie bags in case you forget some, a luxurious pineapple-motif doggie bed, and a little tin of Milk Bones for those mid-night snacks. (Want to see my reaction as I walked into my room? Check out my Instagram Stories, here).

Did I mention that Staypineapple’s mascot is a husky dog named Dash? Oh, yes!! They REALLLLLYYY love dogs.

But, they also love humans as well!

For you 2-legged people, the hotel boasts all the amenities you’re used to from a fine-hotel, plus many others:

• Over-the-top luxurious sheets, blankets, pillows etc. They call it their Naked Experience™ because the bedding is soooo soft, you’ll want to sleep naked (I always do?).
• Pineapple shaped charging stations in the room – to “juice up” your appliances
• Complimentary yellow bikes for you to use and explore the city.
• Delicious, daily complimentary cupcakes in the lobby, along with pineapple infused water.

I cannot recommend the Staypineapple Chicago enough and I can’t wait to visit some of their other hotels in San Francisco, Seattle, New York and San Diego!

But, for now, back to Chicago!

Where to Eat:

After all that travel, and checking in to the hotel, you will surely be hungry. These two spots we visited are a must-see for you and your pooch.

The City Mouse

The City Mouse is a restaurant located inside the Ace Hotel. It serves new American fare including daily brunch & craft cocktails. They allow dogs inside the Lobby (seen in picture above) as well as in the Patio outside. If you look closely, you will notice how the patio was covered in snow!

Do-Rite Donuts

Do-Rite Donuts. Oh my dog! Talk about delicious & delectable artisanal donuts (and in some locations, fried chicken sandwiches!) There are many locations around the city, but make sure to find one that has a patio. Almost all patios are dog-welcoming.

What to Explore:

After devouring all those donuts, you will most definitely need to walk-off some of the consumed calories. Downtown Chicago is a dream of a city to stroll: It is clean. It is organized. It is beautiful!

Make sure you visit the Magnificent Mile if you want to shop (or window shop – note that not all stores are dog-friendly so check before entering). I also recommend taking a stroll near the hotel at night, the city really lights up as the sun sets!

Because I went during a snowy-winter month, many dog-friendly activities were not in-service or were closed.

If you happen to go to Chicago during summertime, here are some activities I heard are PAWSOME:

• Cruise Chicago’s waterways with your pooch! Mercury Skyline Cruises allows you to bring your pooch on a water tour of the city. That’s right, dogs on boats!
• Play fetch and meet native Chicagoan dogs in one of the many, many dog parks around the city.

Important Hami Tips:

1. Sneak into Cloud Gate (aka: the Bean) – If you want to get a picture of your pooch at “The Bean”, then you are going to have to get sneaky!! There are no dogs allowed at Millennium Park. My human and I got there as the sun was rising so there wasn’t a soul in sight. Except one security guard that didn’t bother us because we quickly posed for the picture and then I got carried out in my tote.  (Rules, Meh! I do what I want!)
2. Bring a Tote Bag – if your dog is small enough to fit in a dog tote-bag, make sure you carry it with you everywhere you go. If your dog gets tired after exploring Chicago all day, BAM. In the tote. If you want to sneak into Millennium Park, BAM!
3. Winter Gear – If you are traveling to Chicago between the months of November – April then there is a really big chance that it will be cold, windy and snowing. Bring doggie coats and/or sweaters AND be careful of the salt that they use to melt the snow on the city streets. I HATE/LOATHE/DESPISE dog booties but if your dog wears them, even better. The salt they throw on the sidewalks will burn your doggos paws after prolonged periods of contact.
4. Uber Around for Long Distances – I rode around in an Uber a couple of times (in above-mentioned tote bag) but even dogs that do not fit in totes can take Uber. Make sure that after ordering your Uber, you call your driver to let them know you have a dog. Not all drivers will accept dogs, but there are many who will!

Have you visited Chicago before? Is there something that I should add to my Must-See list? Planning on visiting Chicago in the future? Let me know in the comments below.