Dog-Friendly Vacations in Chicago. A Day in the City of Chicago, Illinois with Dogs.

Pet-Friendly Chicago, Illinois Road Trip

The Best Dog-Friendly Activities in Chicago

Dog-friendly Chicago, Illinois Vacations. Check out my Chicago road trip with Dexter The Dog. Dog-Friendly Activities in Chicago at your fingertips. #raisingyourpetsnaturally
Dog-Friendly Chicago Guide

 

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.

Dog-friendly Chicago, Illinois Vacations. Check out my Chicago road trip with Dexter The Dog. Dog-Friendly Activities in Chicago at your fingertips. #raisingyourpetsnaturally
Dog-Friendly Trump Chicago

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.

Dog-friendly Chicago, Illinois Vacations. Check out my Chicago road trip with Dexter The Dog. Dog-Friendly Activities in Chicago at your fingertips. #raisingyourpetsnaturally
Dog-Friendly Navy Pier in Chicago

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.

Dog-friendly Chicago, Illinois Vacations. Check out my Chicago road trip with Dexter The Dog. Dog-Friendly Activities in Chicago at your fingertips. #raisingyourpetsnaturally
Dog-Friendly Attractions in Chicago

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.

Dog-friendly Chicago, Illinois Vacations. Check out my Chicago road trip with Dexter The Dog. Dog-Friendly Activities in Chicago at your fingertips. #raisingyourpetsnaturally
Dog-Friendly Chicago Patio-Siena Tavern

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.

Dog-friendly Chicago, Illinois Vacations. Check out my Chicago road trip with Dexter The Dog. Dog-Friendly Activities in Chicago at your fingertips. #raisingyourpetsnaturally
Outside dining in Chicago-Siena Tavern

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.

Dog-friendly Chicago, Illinois Vacations. Check out my Chicago road trip with Dexter The Dog. Dog-Friendly Activities in Chicago at your fingertips. #raisingyourpetsnaturally
Outside Patios in Chicago-Siena Tavern

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.

Dog-friendly Chicago, Illinois Vacations. Check out my Chicago road trip with Dexter The Dog. Dog-Friendly Activities in Chicago at your fingertips. #raisingyourpetsnaturally
Pet-Friendly Trump Chicago

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.

Dog-friendly Chicago, Illinois Vacations. Check out my Chicago road trip with Dexter The Dog. Dog-Friendly Activities in Chicago at your fingertips. #raisingyourpetsnaturally
Chicago Riverwalk

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.

Dog-friendly Chicago, Illinois Vacations. Check out my Chicago road trip with Dexter The Dog. Dog-Friendly Activities in Chicago at your fingertips. #raisingyourpetsnaturally
Chicago at night

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.

Dog-friendly Chicago, Illinois Vacations. Check out my Chicago road trip with Dexter The Dog. Dog-Friendly Activities in Chicago at your fingertips. #raisingyourpetsnaturally
Mercury Canine Cruise

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.

Dog-friendly Chicago, Illinois Vacations. Check out my Chicago road trip with Dexter The Dog. Dog-Friendly Activities in Chicago at your fingertips. #raisingyourpetsnaturally
Relaxing Boat Cruise

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.

Dog-friendly Chicago, Illinois Vacations. Check out my Chicago road trip with Dexter The Dog. Dog-Friendly Activities in Chicago at your fingertips. #raisingyourpetsnaturally
Best Dog-Friendly Patios in Chicago-Barrio

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!

Dog-friendly Chicago, Illinois Vacations. Check out my Chicago road trip with Dexter The Dog. Dog-Friendly Activities in Chicago at your fingertips. #raisingyourpetsnaturally
Forest Mushroom Tacos

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.

Dog-friendly Chicago, Illinois Vacations. Check out my Chicago road trip with Dexter The Dog. Dog-Friendly Activities in Chicago at your fingertips. #raisingyourpetsnaturally
Chicago Evening Views

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
  • Navy Pier
  • Navy Pier
  • Siena Tavern
  • Chicago River Views
  • Chicago River Views
  • Chicago Riverwalk
  • Chicago Riverwalk
  • Chicago Riverwalk
  • Chicago Riverwalk
  • Chicago Riverwalk
  • Chicago Riverwalk
  • Pet-Friendly Luxury Hotels in Downtown Chicago. Read our experiences at Trump Chicago and learn about their Trump Pets Program. #raisingyourpetsnaturally
    Trump Chicago Views
  • Pet-Friendly Luxury Hotels in Downtown Chicago. Read our experiences at Trump Chicago and learn about their Trump Pets Program. #raisingyourpetsnaturally
    Trump Chicago Views
  • Mercury's Canine Cruise
  • Mercury's Canine Cruise
  • Mercury's Canine Cruise
  • Mercury's Canine Cruise
  • Mercury's Canine Cruise
  • Mercury's Canine Cruise
  • Mercury's Canine Cruise
  • Mercury's Canine Cruise
  • Mercury's Canine Cruise
  • Mercury's Canine Cruise
  • Mercury's Canine Cruise
  • Trump Chicago
  • Trump Chicago Views
  • Chicago River Views
  • Trump Chicago Views


Do you travel with your dog? Tell me in the comments.

Dog-friendly Chicago, Illinois Vacations. Check out my Chicago road trip with Dexter The Dog. Dog-Friendly Activities in Chicago at your fingertips. #raisingyourpetsnaturally #dogfriendlyvacations #petfriendlyvacations #roadtripwithdog #dogfriendlychicago
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78 thoughts on “Dog-Friendly Vacations in Chicago. A Day in the City of Chicago, Illinois with Dogs.

  1. 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. 🙂

  2. 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!

  3. 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.

  4. 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.

  5. 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.

  6. 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.

  7. 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!

  8. 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. 🙂

  9. 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.

  10. Your doggies are so lovely. I did not know that much. Your blog is interesting I am bookmarking it. A lot to know.

  11. 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.

  12. 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.

  13. 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.

  14. Your pups are absolutely adorable. They are very photogenic too. I didn’t realize that Chicago was so pooch friendly. Good to know.

  15. 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.

  16. 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

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