Welcome

My dog Jager inherited his mom’s sense of adventure and love for travel! He has traveled around the U.S. and Canada. Recently we made a road trip to Chicago. It was an amazing trip. My nephew’s girlfriend, Ashley, joined us. She is from Chicago and made a perfect travel companion. I have always said that if you really want to know someone then travel with them. You really get to see the true person. It was the first time we had traveled together, and it won’t be the last, it was a wonderful experience for all three of us.

It was an impromptu trip. I have a Chase IHG credit card, which I love, but I almost forgot to use my free anniversary night. Chase gives you a free night each year, and you also earn points on each purchase. So, I had my free night and enough points for a second complimentary night. I love the IHG brands. When I was a flight attendant, I stayed at many InterContinental’s abroad. I love that old-school charm and class of the Intercontinental. More recently, I have stayed at the Hotel Indigo chain, which is modern and charming. I have stayed at a few Kimpton brands, and they were charming and unique, too.

My research led me to choose the Kimpton Monaco for our stay. I have stayed at many different 4- and 5-star hotels in Chicago, and I must say this was one of my favorites. The Kimpton checked every single box that we desired for our trip. It was a great location, modern, attentive staff, and it was dog friendly. It was not only dog-friendly, but they went out of their way to make Jager feel at home. I would recommend this hotel to anyone. It would be a great choice for a girl’s, couple, or family trip. It would also be a great choice for the holiday season. If you want to make a trip to Chicago for Christmas shopping and to visit the Christkindlmarket it would be perfect. It is central to the shopping on State Street and Michigan Avenue and about a 5–10-minute walk to the market. I highly recommend this hotel and also signing up for the Chase IHG Credit Card.

We arrived at our hotel just in time for their nightly hosted wine hour. The wine hour offered a nice selection of White, Red, and Rose. It was also dog-friendly. It was fun to mingle with the human and canine guests of the hotel. We then just grabbed dinner outside the hotel at Elephant and Castle. It was nice and relaxing. We had an order of crisps and Caesar Salad. I am on an old-fashioned kick these days, and that was my cocktail of choice. They had a good selection of draft and bottled beers. Ashley went with the Lagunitas IPA. We enjoyed our selections and had delightful service.

Jager enjoyed his first night at the hotel and adjusted nicely. We woke up early and went for a nice walk. I love Chicago and all its bustle, but it is so peaceful first thing in the morning when you pretty much have the streets to yourself. We then had reservations for a scenic boat tour of the Chicago River and Lake Michigan. It departed from the Chicago Riverwalk, which is a destination unto itself. We found a cruise that was specifically for humans and their canines, and it was on Mercury Cruises. I highly recommend Mercury Cruises, even if you don’t have a dog. If you have a dog, it is a must!

Travel is all about experiences and friends. One of the things I cherish most about my travels is the friends that I have made along the way. So, the rest of the day was about old friends, new friends, and old friends becoming friends with new friends. After our cruise, we were starving, as all we had for breakfast was Garrett’s popcorn, which I really love, but not sure it is a complete food group. We met up with two of Ashley’s college friends. We went to a pizza place called Parlor Pizza Bar on Dearborn Street in River North.

Parlor Pizza Bar was great, tasty and a lot of bang for your buck. We sat outside and they were very accommodating for our furry companion. We were 4 (5 if you count Jager). The first thing we ordered was the hummus, and it was huge. We then shared a Margarita and the ALL CAPS and both were very good. I love mushrooms and the ALL CAPS was a base of black truffle cream and an array of mushrooms. My stomach just growled thinking of that pizza. It is something I will try to recreate.

We then headed back to the hotel and met up with one of my oldest and dearest friends, Michael. We became friends during our flying days at World Airways. He lives in Chicago with his partner, Robert. It was nice to throw in Ashley’s friends with my friends, and we made an evening of it. We had dinner reservations that evening at a Mediterranean restaurant in River North, Ema. The place was very stylish. We again sat outside on their beautiful patio. They were also happy to have Jager join us. At this point in the day, he was very tired. I was going to leave him at the hotel, but he had a bad case of FOMO, and his second wind kicked in as soon as we were walking out of the hotel room.

We had a couple of cocktails and a wonderful selection of small plates. I think our favorite was the Ginger Turmeric Labneh. Everything was wonderful, but that was my favorite. We ended the evening with a nightcap at an old-time favorite, Pippin’s Tavern.

The next morning, our final day, we got in one more long walk around the city. I just love the different neighborhoods in Chicago and how they blend. We were on a mission to find the infamous location of the Dave Matthews Band Tour Bus incident. We found it and documented it. Then we headed back to the hotel for our check-out. We thanked everyone at the hotel for their wonderful hospitality and hit the road.

Ashley’s dad and sisters live right outside of Chicago, so we made a lunch stop. We enjoyed some comfort food at Shack Shake in Oakbrook. We then walked around the outdoor mall before making a final trek back to St. Louis. It was a Sunday, so it was a painless drive with minimal traffic.

It is always a bittersweet feeling when a trip ends. I especially cherish this trip, as it was my first trip with Ashley, and it was a great opportunity for us both to catch up with old friends. It was two different worlds coming together, but instead of colliding, they complimented each other. So, not only did our hotel check every single box, but so did this trip. In my opinion, a successful trip includes friends, learning, fun, and adventure. The memories will stay with us forever and if you are like me, the best thing to do is start planning that next trip. Ashley, get ready for the Epcot International Food and Wine Festival at Disney World in November.