Pet-Friendly Chicago, Illinois Road Trip
The Best Dog-Friendly Activities in Chicago
Disclaimer: This is a sponsored post. However, I will always offer my readers an unbiased and honest account of my experiences. However, I will always offer my readers an unbiased and honest account of my experiences. Your trust is very appreciated, and never taken for granted. ~Tonya, Dexter and Angel Nutter
Dexter the Dog and I love taking a good dog road trip. But, it’s always more fun with friends, so we invited Levi the Dog and his mom, Chris, and hit the open road. This pet-friendly vacation would be in Chicago, Illinois. In the city, to be exact.
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Dexter and I have visited Chicago in the past but never stayed in a pet-friendly hotel in downtown Chicago. I thought this would be a great time to stay in a luxury hotel right on the Chicago River. This would allow us to spend our dog-friendly weekend getaway on foot and never need to drive on the busy Chicago streets during our stay.
Trump Chicago would be the perfect quality hotel for the weekend. Trump International Hotel & Tower Chicago is situated on the Chicago River with easy access to the Navy Pier, The Magnificent Mile, dog-friendly fine dining, and the Chicago Riverwalk. This would be the perfect pet-friendly accommodation for the weekend.
Our first stop in our dog-friendly Chicago weekend was the Navy Pier. The Navy Pier in Chicago is a popular tourist destination, and the outside common areas are dog-friendly. There are a variety of restaurants on the pier offering outside dining that allow dogs. If you are without a dog, there are loads of inside shopping opportunities. Dexter and Levi enjoyed sniffing the fresh Lake Michigan air as they watched the waves and birds go by.
In the early 1900s, revered architect Daniel Burnham envisioned an urban public pier utilizing Chicago’s lakefront for both attractive public space and shipping. Burnham died before his vision was complete, and the Harbor and Subway Commission hired architect Charles Sumner Frost to design and plan the pier. The Navy Pier’s grand opening was in 1916, and it was the first of its kind to integrate the shipping business with public entertainment. The Navy Pier in Chicago is the longest public pier in the world today.
After the dogs toured the Navy Pier, our stomachs were rumbling. It was time to find an outdoor dog-friendly patio in Chicago. Chicago isn’t just known for its stunning architecture, it is also known for its tantalizing cuisine. When visiting a new city, it can be a challenge to find a dog-friendly restaurant, especially one with scrumptious food.
That’s where DineAmic Group came to my rescue. DineAmic Group not only serves some outstanding food that Chicagoans and tourists love, but they also offer a delicious and dog-friendly menu dedicated to woman’s best friend. They created a dog-friendly menu at each of their four Chicago restaurant locations: Siena Tavern, Bar Siena, Barrio, and Public House.
Siena Tavern’s from-scratch menu and convenient location made it our first choice. This Chicago dog-friendly restaurant has a modern design and a contemporary menu. The outside patio is spacious and offers large umbrellas for shade. Siena Tavern’s lunch menu includes antipasti, salumi, soup, salad, house-made pasta, burgers, sandwiches, and a variety of unique sides.
When I’m traveling, I try to order food that’s outside the norm for me, which isn’t that hard to accomplish, since I have a pretty small list of menu items I typically order. Turkey Porchetta Club, it was! This is not your ordinary turkey club sandwich. This handcrafted sandwich is filled with turkey porchetta, avocado, crispy pancetta bacon, butter lettuce, vine-ripe tomato, and roasted serrano aioli. The side of fries that came with my meal was topped with freshly grated parmesan. Chris ordered the Tavern Burger. This thick hamburger is topped with Hook’s cheddar, grilled onion, smoked grain mustard, crispy kale, and oven-dried tomato all inside a brioche bun. Dexter and Levi ordered the burger patty.
The food was heavenly. Everything was fresh and mouthwatering. The dogs devoured their burger patties. What I really loved was that the burger patty was simply grilled with extra virgin olive oil. Nothing bad or unhealthy.
After dining at Siena Tavern’s dog-friendly patio, we walked around downtown Chicago. It was fun strolling up and down the busy Chicago streets and looking at all the amazing architecture. Chicago is known for its innovative architectural buildings and designs. The city’s skyscrapers, bridges, homes, and business buildings are quite breathtaking.
After walking around downtown Chicago, we headed back to Trump Chicago for a little rest. It was very convenient to be so close to all of our adventures. We all jumped up into our luxurious queen-sized beds and looked out the floor-to-ceiling window at the incredible view of the city.
Spending a dog-friendly weekend in downtown Chicago meant that we needed to keep up the pace in order to enjoy as much of the town as possible. Next up on our dog-friendly Chicago tour was the magnificent Riverwalk spanning 1.25 miles along the Chicago River.
One of the best parts of this bustling walk is that it’s accessible and accommodated Dexter’s dog stroller. During our evening walk, we enjoyed interacting with other tourist and locals as we took in all the beauty of the river. The Riverwalk features a variety of neat venues, restaurants, and seating areas. The views of the nighttime Chicago skyline were just awe-inspiring. It was a perfect end to our first night in Chicago.
Saturday morning was going to be a fun-filled day. We were invited to ride the Mercury, Chicago’s Skyline Cruiseline’s Canine Cruise! I was quite honored to be invited because this dog-friendly Chicago boat cruise was actually reserved by Real Dog Moms of Chicago. When they heard Dexter and Levi wanted to take the Mercury, Chicago’s Skyline Cruiseline’s Canine Cruise, we were welcomed with open arms. I wasn’t surprised, when I read more about what Real Dog Moms of Chicago are all about.
The Real Dog Moms (Dads, too), get together for monthly events and activities. You might find them getting together for a crafting event, pool party, or even a dog-friendly boat ride along the Chicago River. But, it’s not all fun and games. The Real Dog Moms of Chicago actively embark on fundraising events for local animal shelters and dog rescue groups. Their mission and goal is to one day open a senior dog sanctuary.
Our dog-friendly boat ride on the Mercury’s Canine Cruise was a real treat. The boat was filled with dog lovers and dogs of all shapes and sizes. Our 90-minute boat cruise was entertaining and educational. The narrator talked about all the city’s famous buildings and the local dog-friendly sites. We also received a great dog-friendly map and guide.
The Mercury’s Canine Cruise offered plenty of seating, water bowls, and even a newspaper-lined restroom for the dogs. That was such a neat perk. The boat ride was so relaxing and a perfect way to spend quality time with Dexter while enjoying Chicago’s waterways. I can see why the Mercury’s Canine Cruise is a favorite attraction for both Chicagoans and tourists.
After our canine cruise, we grabbed a little food while strolling the Riverwalk once again. It’s such a great walk, and the sights and views were worth a second look. At one point, we sprawled out on some open grass and people watched. Kayakers, boaters, fishermen, and people walking their dogs were some of my favorite passersby. I was waiting for someone to reel in the big one, but it didn’t happen.
The pups looked like they needed a little nap before dinner, so we walked back to Trump Chicago for a rest. It was a great experience having such a close dog-friendly hotel in Chicago, one we could pop in and out of during our adventures.
After our rest, we headed to Barrio, another DineAmic Group with a Puppy Patio Menu. Barrio is situated in the heart of River North. Barrio’s fare is an innovative take on traditional Mexican food with pan-Latin and American influences. The creative menu incorporates a shared-plate presentation offering locally sourced, sustainable ingredients with an emphasis on organic, as well as paleo and gluten-free options. The BARK-IO Puppy Menu offered skirt steak, burger patty, chicken breast, and dairy-free woof cream.
I ordered the Forest Mushroom Tacos. The hand-pressed macienda heirloom corn tortillas were petite and soft, not like the yellow hard-shelled tacos I was accustomed to. The delectable shells were filled with mushrooms, white truffle, garlic crema, cotija cheese, and gruyère francés. The flavor pouring out of these mushroom tacos was phenomenal. I’ve never tasted such a delicious taco!
Chris ordered the chopped salad. The salad was loaded with romaine, tomato, spiced bacon, Hass avocado, charred corn, cotija cheese, cucumber, black beans, pickled red onion, roasted poblano, and crispy hominy dressed with a garlic miso vinaigrette. Chris said that the chopped salad tasted fantastic and what makes it taste even better was the ambiance.
The evening atmosphere of Barrio was quite enjoyable. The servers were very calm, polite, and attentive. The outside patio was filled with lush green plants, and there were lights strung all around, creating a warm setting. The patrons at the neighboring table were intrigued by Dexter and Levi’s good manners and kept saying how cute and well-behaved they both were. I’m sure it had something to do with the fact they were being rewarded with bites of their grilled chicken breast from the Puppy Menu. 🙂
My only regret from our dinner was that I didn’t order one of Barrio’s distinctive desserts such as The Flowerpot or Warm Chocolate Mole Cake. You’ll have to take a peek at their menu to see just what I missed.
After our serene evening, we were ready to call it a night. We headed up to Trump Chicago for our last night’s sleep. A perfect way to end our dog-friendly weekend in Chicago.
A big thank you to Trump International Hotel & Tower Chicago, DineAmic Group, Mercury, Chicago’s Skyline Cruiseline, and Real Dog Moms of Chicago for making our trip possible.
More Photos
Navy Pier
Do you travel with your dog? Tell me in the comments.
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Great article! I’m sharing this with my bestie who just got a puppy, and needs care and training tips!
Thank you!~ I appreciate that.
Thanks so much for this, I’m going to send the link to my bestie who just got a new puppy, and is looking for training/care tips!
Thanks!
Looks like you had a lot of fun! That sandwich looks so good!! I don’t have a dog right now, but hopefully we will get one soon. 🙂
The food was totally amazing! Chicago is a blast, even for those without dogs. 🙂
Looks like you and your dog had a lot of fun there. Taking care of the dog is really a tough job at times.
We had a great time. Dexter and Levi love road trips.
Most establishments especially restaurants do not allow pets inside so that’s amazing that your pets could travel with you. I love Chicago and I would love to visit it again with our chihuahuas!
You should! And your chihuahuas would have plenty of space. 🙂
First of all these two are so adorable. arent they just the cutest thing. Really good if you have pets to know of the dog freindly places in the area.
Thank you Nathan. Us pet people are always looking for fun dog-friendly vacation spots. I love to share our adventures.
Oh it was nice to know that Chicago is a pet-friendly city. We are still fighting to have that kind of environment here in Manila.
Keep up the good fight!
These cutie doggies look so happy and healthy. If I had that life, I would be, too. hihihi Lucky dogs 😀
Thanks! Yes, very happy pups.
This is such an interesting article indeed, I love reading about dog friendly vacations. Chicago seems like a great pet-friendly place to be visiting.
Thanks, Elizabeth. Chicago really does have a lot to offer people traveling with their dog.
I love animals – especially dogs and cats. I think you can tell a lot by how people behave around animals. Your pups are lovely 🙂
Thanks, Mike.
I did not know that a town could be pet friendly nor not. Anyway I love the idea of pet travelling and pictures are cool!
Hi Ben. Yes, some towns offer more activities, parks, and greenery for dogs to enjoy. Chicago is pet-centric and actively engages in the pet community.
Your dogs are so cute!! Had to get that out of the way lol.
I love traveling with my dog! I’ve been traveling with him for the past few months and it’s crazy when you start to realize how limiting it can be. But it’s also so amazing when you do find fun vaca things to do with your dog because it usually means other dogs are there too! So the more the merrier.
haha Thanks! It can take a little pre-planning to ensure a good time for all of us but ends up being so worth it. We find some really unique adventures traveling with the pups.
Wow Dexter and Levi looked like they had a blast. I just love how pet-friendly chicago is with all its pet-friendly activities and dining options available. Would love to take my Annabelle there on a road trip. She’d love it!
Hi Jennifer. Chicago was amazing and so much fun. The pups really enjoyed all the dog-friendly activities and loved the family time. You should take Miss Annabelle!
Wow! Great read. It seems like you had a great time in this dog-friendly atmosphere. It so good to know that there are also the places for dogs. Chicago evening view is just amazing. And ya your dogs are so cute and fluffy. 🙂
Thank you! Yes, those views were stunning!
it’s great when a city (a big one like Chicago) is so pet friendly! Many times public places are not ready to welcome our faithful friends !
Thanks, Sabrina. I totally agree. I’m so happy to see more and more places welcoming well-behaved dogs and their humans.
Even we guys have never stayed in a pet friendly hotel either. Dog friendly vacations seems to be a great idea!
Traveling with dogs makes the entire trip an fun adventure.
We love to bring our pets on travel trips with us when we can. I love that there would be so much in Chicago that we can all enjoy together.
I love hearing that others travel with their dog. It’s so much fun and such a great way to enjoy a destination. 🙂
Great post! Dog owners can sometimes had a hard time finding pet friendly places in big cities.
Thank you. It can be a challenge, but a little research is very helpful. Chicago is very dog-friendly.
This is great information for anyone with a dog. I’m thinking of getting one but am worried that it’s going to be really hard to travel. Good to know that there are options!
Hi, Maartje. It’s definitely something to think about. I always travel with Dexter and that determines my trip. I will be working on an article about leaving dogs at boarding/pet sitter while traveling. Stay tuned.
Your doggies are so lovely. I did not know that much. Your blog is interesting I am bookmarking it. A lot to know.
Thank you!
This is great! My best friend lives in Chicago and I definitely want to keep this guide in pocket for future use 🙂
Wonderful! Thank you for sharing it with her.
cute doggies! as a dog mommy myself, i always appreciate establishments allowing dogs inside. dogs are not pets, they’re family 🙂
Thank, you. I totally agree. 🙂
Going to bookmark this site for when I have my dog. Lots of informative posts you have here. Great job!
Super happy to have a new follower! Good luck on the dog search.
I’ve always wanted to take my dog on a trip with me! It looks like Chicago would be a great place to do that. 🙂
Yes! Go for it. A little planning ahead makes for a great trip.
awwww they had so much fun! Chicago is such a beautiful city, and I am glad there is plenty of things to do with pets as well!
They had such a great time! Chicago offers a lot, we can’t wait to go back.
Your furry babies are so adorable and I’m glad to know that they enjoyed traveling with you in Chicago. Yay for pet-friendly establishments!
😀 Thanks. I’m so thankful to places that welcome well-behaved dogs.
Chicago is one of my favorite cities to visit! Haven’t done so yet with our doggies! This is super helpful info! Thank u!
Me too. You must try it with the doggies. Such a unique way to learn about a destination.
First of all its such a cute do you have got, because I know and I am also a dog lover. Second of all its going to be such a lovely time for dogs also to roam around and see new places.
😀 Thank you. The dogs really enjoy dog-friendly vacations and trips. They love checking out all the new sights and smells.
Such a nice post and I am so glad to know that there is a place that allows pets in their building and a place that the owner and the pet will enjoy being together.
Thank you. Yes, we love finding dog-friendly establishments to patronize. Chicago had a lot of dog-forward things to do and see.
Your pups are adorable! I am jealous how dog-friendly your country is and how much your dog get to enjoy outdoor.
🙂 Thanks. Check around and ask. You might be surprised at home many establishments will welcome well-behaved dogs.
While I no longer have a dog due to allergies, I wouldn’t mind visiting Chicago again someday. It sounds like the perfect destination to visit!
Sorry about that. I too am allergic to dogs! https://raisingyourpetsnaturally.com/dog-allergy-treatment Chicago is an amazing place to visit. I hope you get a chance to go back.
Oh my days! Dexter and Levi are adorable! It is lovely to see that so many places are dog-friendly. They are part of the family after all! 🙂
🙂 Thank you! Yes, family indeed.
Oh my days! Dexter and Levi are adorable! It is lovely to see that so many places are dog-friendly. They are part of the family after all! 🙂
Thank you. Yes, they are family. We love supporting businesses that support us dog lovers.
Thank you for sharing your dog-friendly trip to Chicago and all the excellent photos.
Thanks, Pat. We had so much fun and I love sharing our adventures.
I never really thought about going to travel with my fur babies before, it looks beautiful though. May need to add it to my want to do list.
It’s such a great way to travel. It makes you think outside the box and you can find some real gems.
This seems so fun! I love trips where you can bring your furry along. Thanks for sharing this!
You bet. It was so much fun.
Your pups are absolutely adorable. They are very photogenic too. I didn’t realize that Chicago was so pooch friendly. Good to know.
Thank you. Chicago had loads of dog-friendly activities. We want to go back to experience more.
I am not a dog owner but I sometimes do take care of my friends’ pets when they go on holiday. I know how hard it is to find a dog friendly restaurant to have dinner at when you have a four legged friend accompanying you. It’s great that Chicago has so many options for people who like to take their dogs on holiday with them.
Thanks, Joanna. I’m sure your friend appreciates you taking such good care of her pets when she’s gone. 🙂
I live in Indianapolis so Chicago is about 3 hours away, and it is my favorite place to let my inner foodie roam free! I never thought about taking a pet, this is pretty good info to have
Thanks, Erica. Then you must take our dog. I’m hoping to go to Indianapolis next spring. 🙂
Having lived and worked in Chicago years ago, I was interested to read this post to see how your experience was as a visitor with 2 cute doggies. Glad it all turned out so well including the weather. How great to know there are pet owner groups that can have boat sightseeing outings on the Chicago River. What fun! Pinned.
Hi, Deborah. What a great city to live. We have a lot of Cavalier friends who live in the Windy City. 🙂 Thanks for sharing.