Our Weekend in Chicago

We enjoyed a little family getaway to Chicago this month — and, yes, by family I mean Dan, Henry, and me! Dan had some hotel points that were set to expire at the end of March, so we decided to enjoy a weekend downtown at the Park Hyatt. We’ve been up to the Chicago area a lot since getting engaged, but our weekends are usually packed with wedding planning or family time in the ‘burbs, so we never have free time to just hang out on our own in the city. It was nice to have a laid-back weekend there with a whole day itinerary-free.

We drove in after work Friday night and started our Saturday early with a walk. We had to walk Henry anyway, so I devised a route to take a long walk along the lakefront to North Avenue Beach and the Lincoln Park Zoo to scope out our upcoming engagement photo locations.

The city views from the lakefront at the beach are phenomenal, and I cannot wait to take engagement photos there with that stunning backdrop! From there, we walked to Lincoln Park Zoo’s pavilion and South Pond, then circled back through Old Town, stopping along the way for a coffee at Elaine’s and a dog toy at Pet Stuff.

We ended our 6-mile walk with cupcakes from Sprinkles — one sprinkled cupcake for Dan and me, and one dog cupcake for Henry. He absolutely loved his treat! And he doesn’t normally care much for food or treats, so it made us happy to watch him devour it.

Above is Henry after his bath in a luxurious soaking spa tub, eating his Sprinkles cupcake, and then lounging on our bed. He is obviously getting quite accustomed to 5-star hotel life…

We went to Bub City in River North for a late lunch, opting for a spot with March Madness TVs in close proximity. We enjoyed some fried pickles, Nashville hot tenders, and Bud Light drafts while talking and eyeing the games occasionally.

Henry was such a gem in the city! He took to pounding the pavement (and peeing on it) right away, and per usual, we couldn’t go anywhere without adoring oohs and ahhs over his cuteness.

We decided to try Gilt Bar for dinner, because I’ve heard amazing things about it for years now, it was easy to walk to from our hotel, and we could get a reservation at a great time. Unfortunately, it was a bit disappointing. I wasn’t blown away by the food, especially because my salmon was really rare. The ambiance seemed nice, but we were seated right by the entrance, so we didn’t really get to experience much of the restaurant. And when we asked about going to their Library bar after, we were told there was a two-hour wait. It just seemed pretentious.

After dinner, we stopped into the Shamrock Club down the street, which is the complete opposite of Gilt Bar but exactly what we wanted: a low-key and cheap drink. Megan met up with us there, and after a few drinks, we set off for Three Dots and a Dash but scrapped those plans because we were not in the mood to wait an hour and a half in line in the cold for a gimmicky tiki bar. We ended up at Fado’s because there was live music and at that point, we were lazy and just wanted something easy.

Megan came back to the hotel with us to meet Henry, and we took him outside on a walk together to Sprinkles to hit up the cupcake ATM (just your usual 2 a.m. food decision…). We were bummed they’d sold out of dog cupcakes! Poor Henry missed out. Luckily he doesn’t know the difference. We said our goodbyes to Megan and crashed shortly after devouring both a vegan red velvet cupcake and a sugar-free red velvet cupcake. We had to get both and eat both for comparison purposes, of course (drunk logic at its best).

The next morning, we enjoyed quiet time in our room before checking out. Dan went to get our car at a valet garage nearby and discovered they hadn’t followed his instructions to turn off the lights, so the battery was dead. And he also discovered the key doesn’t actually function to open the door without power, so it turned into a bigger problem than expected. A couple hours later, I was still chilling in the hotel lobby with Henry (a sleeping angel, per usual) and we’d missed our cake-design appointment at Michigan Shores. Fortunately, it didn’t set us back from meeting my parents for lunch at Dengeo’s.

We ended the weekend on a high note by stopping by Gillson in Wilmette. It happened to be National Proposal Day (who makes up these “national” days?) and we happened to be at the spot where Dan proposed nearly a year ago! It was Henry’s first time to the beach, and he loved it.

We took him to the dog beach, and of course, he immediately ran up to every dog and every human to make friends.

The next time we’ll back in the city will be for our engagement photos in a couple of weeks! I’m excited to work with our wedding photographer for the first time. And get some new family photos with Henry, of course.