Traveling With a Dog: Chicago
As a little girl, I dreamed about going to see “The Bean” in Chicago. When I became a mother to a little girl dog, I passed this dream onto her. So, when our birthdays came up last November, we planned the trip to visit the city where the famous bean was held.
During our chilly November trip, we left from Pittsburgh, stopped in Cleveland, stayed in Merrillville outside of Indiana Dunes National Park, and took a day trip to windy Chicago. Another reason we stopped in Chicago was to visit World Fair locations after I read Devil in the White City by Erik Larson. If semi-famous history locations aren’t for you, this itinerary may not be step-by-step perfect, but it is also still worth your while for dog-friendly locations.
Because this trip was taking place in November, I wanted to ensure Reese was kept warm enough, so the activities were shorter, but there were a lot of them, and could be lengthened depending on the time of year. For us, this was essentially our dream Chicago trip, and we hope it makes a great outline for yours as well!
Reese unpacking at Tru by Hilton Merrillville.
Where to Stay
Because we were also going to Indiana Dunes National Park during this trip, we stayed closer to the park for convenience as well as a cheaper hotel stay. Our go-to hotel is always Tru by Hilton. It is a modern Hilton chain that was created for travelers and those looking for a more modern and young hotel feel. The rooms are always impeccably clean, and I’ve never had a bad experience. In conclusion, I’ve never been disappointed, have always been impressed, and I get giddy every time I book another stay. Sometimes we look forward to staying at Tru by Hilton more than going to the place we booked the hotel for.
I recommend making a free Hilton Honors account if you are booking through their site for extra savings, and if you are fully set on going on the trip, choose the non-refundable option. It’s never done me wrong. The chain is very dog-friendly with dog stations outside the hotel and waste bags available. Dogs typically cost $50-75 per stay, and if you have a service dog, they stay free. For people, they offer complimentary breakfast, and most locations also offer free parking.
If you are looking for a similar stay in Illinois rather than in Indiana, there is Tru by Hilton Naperville Chicago, but arguably, I think it would be a great idea to stay at Tru by Hilton Merrillville, like we did. One reason comes from them being almost the same distance in driving time away from Chicago. The second reason is that we very much enjoyed taking Reese to Indiana Dunes National Park, so if you have time around going to Chicago, it is worth stopping in and taking a hike.
What to See
We started off the day by eating breakfast at the hotel, putting on our winter jackets, and then we were off! Chicago does have a hefty amount of street parking, so starting early in the day can be beneficial if you want to snag a street spot and use the meter.
Reese and I enjoying the fall foliage in Jackson Park.
Jackson Park, Garden of the Phoenix, and the Statue of the Republic
To start, we went to Jackson Park. Designed by Olmsted, it is full of beautiful greenery and history. We began with a walk around the park and made our way towards the Garden of the Phoenix. Dogs are not allowed in the Japanese Garden, so we took turns going to see it and the Yoko Ono art piece. Even if you don’t have someone able to watch your pup while you venture to the garden, I recommend going to Jackson Park while you are in Chicago to give your dog a bit of organic adventure time before you head into a rather concrete city.
If you’re also here for the history, right outside of Jackson Park is the Statue of the Republic replica. Originally built for the 1893 World’s Fair, she is a beauty and a great photo spot. If you’d like to stop by the location of H.H. Holmes hotel, this is also a good time to do so, but just know that there are no signs or markers. It is simply a postal office now with normal buildings surrounding it.
Clarence F. Buckingham Fountain
Heading deeper into the city, we first stopped at the Clarence F. Buckingham Fountain. Since we went in November, the fountain was consequently turned off, but I assure you, it’s a beautiful place to walk, as well as just being an art piece that is still stunning with no water. The fountain is massive, and the gardens surrounding it feel like a bit of Versailles. If you go in the spring, summer, or early fall, the fountain is naturally a must-see. If you aren’t interested in the art aspect of the fountain, then it’s okay to skip. We were able to find street parking here, but after we left, we parked in a garage due to the busy streets around Millennium Park.
Reese and I with The Bean!
The Bean and the Route 66 Begin Sign
Now is the time for the main attraction: The Bean, aka Cloud Gate. During our visit, the ice-skating rink below was open, making it even busier, but also more magical. The Bean is so fun to see in person, and every visitor was just as excited to be there as we were. This is the perfect picture spot, and we were the only ones there with a dog, surprisingly enough, so Reese got a lot of attention and love. Close by are a ton of gift shops, so naturally, we got a mini ornament version of The Bean for the Christmas tree. We love Cloud Gate!
Right across the street is another attraction, the Historic Route 66 Begin Sign. There is an informational and cuter version of the sign, but right to the side of it is the historic Route 66 sign. Admittedly, this meant almost nothing to me and Reese, but of course, we still took pictures with both. Reese is a big city girl and loves walking among the people on the sidewalk, so this was one of her favorite parts of the day, and she was chipper as ever, even in the cold. We spent a lot of time in this area, window shopping and looking at all the buildings, and if the weather permits, we suggest doing the same. In our experience, everyone was so polite and adored Reese, so we enjoyed our time immensely before heading off to our final attraction.
Reese admiring the general splendor at Navy Pier.
Navy Pier
Yes, Navy Pier is very touristy, but it also offers amazing sights of the water, and as Pittsburghers, we wanted to see the Ferris wheel as well. We got to Navy Pier in the early evening and spent a lot of time just walking the pier and watching the water and people. As a note for the history people, the original Ferris wheel was built for the World’s Fair by Ferris (from Pittsburgh, subtle brag), and the one at the Navy Pier is to honor the original. It’s also just fun to see. The pier is nice to be at for sunset, especially on a clear day, so plan accordingly for that. It is also especially cold in the winter because of the water, so plan for that as well. Overall, Reese loved her time at every attraction we went to, so I hope your pup does as well!
Where to Eat
We weren’t in Chicago for the food, considering I didn’t think we would find a place to eat that was outside, warm, and would allow Reese. So, there were a lot of factors, but we aren’t very picky. While at Millennium Park, we found some spots that suited our fancy, and I don’t regret our choices at all. To warm up, I grabbed some chai from Chiya Chai. If you aren’t a chai fan, there are so many cute and nice places to eat on S Michigan Ave right next to Cloud Gate, so there is something for everyone. Though I will say, my mum is also not a chai fan, and she loved her drink from Chiya Chai, and it was the perfect way to warm our bodies from the wind.
Before leaving for Navy Pier, we also grabbed a Korean corn dog from Kong Dog. We love Korean corn dogs, but if you don’t, again, there are many, many options to choose from. My last recommendation is a must, though, so don’t take it lightly. After walking Navy Pier, we wanted to finish the night with something extra cold before heading back to the hotel: ice cream. I found Eli’s Ark on TikTok and knew I had to go, and it was even better than I could have imagined.
My puppy ube marshmallow ice cream from Eli’s Ark.
Eli’s Ark is an ice cream shop that adds toppings to the ice cream to resemble different animals. It’s not only cute, but the ice cream was amazing. I got ube marshmallow, and I’m not sure if it was a seasonal flavor, but it should be permanent. They did allow Reese inside if she didn’t bark and was well behaved, but she is a long-haired dog, so I don’t like bringing her into restaurants in case she sheds, and a sudden breeze blows her hair onto another customer’s ice cream cone. We stood outside to eat the ice cream, and truth be told, it’s never cold enough to drag me away from ice cream. Eli’s Ark was truly the perfect way to end our time in Chicago.
After saying goodbye to the city, we made our way back to the hotel to snuggle in and watch a classic movie, maybe even one about two women who commit certain crimes and become jail songbirds. Maybe.
Full Itinerary
Everyone’s trips look different and can be adjusted to best fit their furry companion, but I hope this gave a base outline for a great trip by itself! For our full itinerary, including driving time, please see below. We hope to see you on our next trip!
Reese’s full Chicago itinerary.
