Table of Contents

INTRO

Shortly after Nick and I received our COVID-19 vaccines, we were in need of a quick getaway (this was in 2021). At the time, we still lived in Michigan and decided to do a 2-night trip to Chicago, which is an easy drive from Ann Arbor. Leia had just finished an intensive obedience training program, and it was her first time visiting a large city (look at her now, a Seattle city dogo and travel guru). We had a blast, which was partially because of our careful planning to ensure that she felt comfortable during her first “big city” experience. Below summarizes our tips, tricks and recommendations for successfully navigating a Chicago trip with your dog.

Your best bet is to drive into Chicago, as the Amtrak and airlines are not yet pet friendly. (Can we change that?) Once there, we used our car to drive from Chicago to Evanston and Montrose Beach. Otherwise, we walked to places that were close to our hotel. Because it was the summer, i.e., very hot, we also utilized Uber-pet and had a terrific experience with it (now that we live in a large city, we use Uber-pet fairly frequently).

**Note, this guide is mostly applicable to dog owners, i.e., there are better Chicago guides out there if you’re not bringing Fido.

LODGING

Claridge House, ~$165+/night | Review: 4.4

Airbnbs are harder to come by in Chicago. We wanted an affordable option in a quieter location that was easily accessible to the restaurant scene. With that being said, there are many terrific dog friendly boutique hotels in Chicago. We opted for the Claridge House, a 4-star, lower-priced hotel in the Gold Coast. I would recommend the hotel for those looking for an ideal combination of affordability, location, dog-friendliness, and cleanliness. Note that the rooms are small and if you want to spend more, there are better options.

So, if you have a larger budget, I’d check out the Kimpton Hotel Monaco, which averages ~$350/night (prices dip in “off season”). The Staypineapple, An Iconic Hotel in the Loop is also a great option and average ~$325/night. Note that both of these options are in the heart of the city.

THINGS TO DO

Our time was short in Chicago, so we had three major day-time, Leia friendly activities. 

Walk around Northwestern's Campus

I had never seen Northwestern’s campus before. The university is located in picturesque Evanston and is nice to walk around. 

Montrose Dog Beach

We typically stay away from dog parks for many reasons. Nonetheless, this spot on Lake Michigan offers tons of space for dogs to swim, and if you get there at an off hour, it is nice. While it was packed when we were there, Leia, my little fish, retrieved her ball out of the lake for what felt like hours, and it was the purest definition of happiness. 

Walk Around the Gold Coast

We enjoyed walking around the Gold Coast, admiring the Chicago architecture, and walking close to Lake Michigan.

FOOD

During this trip, we had three criteria for picking a dine-in restaurant: 1) quality of food, 2) ability to make a reservation, 3) ability for the patio to give Leia a comfortable space, i.e., if we’re going to sit on a sidewalk corner, next to a busy road, then it might not be a good option for us. The below options satisfied our above criteria: 

Siena Tavern

With it’s own pup menu, how could this place not make our final selection? The favorites here include Coccoli, Squid Ink Linguine, and Gnocchi. I recommend all of these dishes, though felt the Gnocchi impressed me more than the Linguine. A solid Italian-American spot, with a fun atmosphere. AD’s Review: 4.4. 

Nico Osteria

Nico Osteria is located in the Thomson Hotel, but the restaurant is an easy walk from the Gold Coast. The Tuna Squid Inc Pasta was a fantastic dish that pleasantly surprised us (I would go again specifically for this dish). Leia was constantly replenished with cold water and lots of compliments. AD’s Review: 4.45

TAKE AWAYS

Brining dog to a city can be overwhelming and, depending on the dog, requires a bit more planning. If you think that bringing your dog is more trouble for both you and your dog, that’s fair. Leia is an interesting medium: she loves being with us, enjoys going out in public, has conquered almost all of her reactivity issues, and so as long as it is feasible, we bring her. She also, however, has a wild side, and thus we give her avenues to activate her high-drive tendencies when we’re traveling, e.g., intense play at the lake! We are also over-the-top millennial dog owners, and sharing experiences with her is fun for us. Below lists my TOP pieces of advice if you do bring your dog on a city vacation with you:

  1. Give your dog a job to do: When we’re in large crowds and cities, because there’s SO much going on, focusing on us is the “easiest” thing for Leia to naturally do, BUT, we always give her a simple “job to do,” i.e., heal, sit, stay, place, etc.
  2. Figure out the bathroom situation: We had a horrific time getting Leia to go “potty.” It is difficult to find luscious grass in Chicago. Look for parks that have grass ahead of time. If you have a male, you might not have a problem with it, but Princess Leia is far too proper to pee on the sidewalk .
  3. Be careful of the heat: It was HOT when we went. We used Uber-pet to go short distances because it was not worth the risk. We also now use shoes if pavement gets hot.
  4. RECALL: Make sure that your dog has recall before going into high trigger environments, such as a dog beach. Recall is so important in ensuring the safety of everyone (your dog, other dogs, people, etc.).