My Weekend in Chicago 2017

Hello lovelies! As I mentioned in my last post, I did some traveling recently. I flew to Chicago toward the beginning of the month for the weekend for my friend, Julia’s, birthday. Our other friend, Tabitha, also flew in for the celebrations. And, as always, the weekend seemed to go by much too quickly. While a good portion of the weekend was spent catching up and just generally enjoying each other’s company, we did do a few fun things as well. Tabitha and I were in charge of planning the entire weekend and I thought I’d share a few of the things and/or places that we went.

If you’re planning a trip to Chicago anytime soon, I would definitely recommend trying any of these places.

the three of us on the speedboat

Speedboat at Navy Pier

I’ll admit this was something I was initially not too keen on but it turned out to be really fun. When I think speedboat ride, I think of the kind of ride where your dad or uncle takes out the family speedboat and does tight donuts on the lake while going super fast which is not really my thing. But this was great. It was a large, bright yellow boat and while we did go pretty fast, there were no sudden swerves or anything. We didn’t even get wet although it’s not guaranteed that you’ll stay dry. Our guide was entertaining as well. He had a fairly dry sense of humor so I’m not sure if the other passengers got his humor or were just waiting for the boat to start moving but my friends and I were cracking up listening to him go through his spiel.


Pizza Prosciutto e Rucola
Ricotta Vasi
Gnudi Pomodoro

Davanti Enoteca Italian Restaurant

Let me just start out by saying the food at this place was INCREDIBLE! Seriously, 10/10 would recommend. This is where we ate dinner on Saturday and honestly, we were just looking for something within walking distance of Howl at the Moon (btw, it’s like 2 blocks away). I take full credit for finding this place. It caught my eye not only because it was nearby but because it also boasted homemade pasta noodles. I will say, one thing we didn’t realize until we arrived is that it is a “share for the table” restaurant meaning that you order a handful of dishes for the table to share. This made the meal a bit more expensive than we had originally anticipated BUT it was totally worth it. We ended up ordering pretty much everything our waitress recommended and she did not steer us wrong. I was so full by the end of the meal but man, everything was so good.


the amazing fiddle player

Howl at the Moon (Dueling Piano Bar)

I didn’t realize at first that this bar was a franchise. I knew there was a Howl at the Moon in Indianapolis because I’ve heard good things about it, but I hadn’t realized that there were more locations until Tabitha forwarded me their link as a night out suggestion. It was pretty fun. We went with a birthday package that included a reserved table for 4, jump the line and waived cover charge privileges, a birthday drink and shot for the birthday celebrant, and a $40 gift card that could be put toward our drinks. All in all, it was a great deal and a fun night. The night that we went, we shared the place with about 5 bachelorette parties in addition to the other regular patrons.

The musicians were all pretty impressive as they began with just the dueling pianos but slowly added instruments (drums, guitar, etc.) as the night went on until there was a more complete set-up. The reason the musicians were impressive was because each musician seemed able to play at 2-3 instruments and appeared to all just switch instruments at random. By far the most impressive however, was the fiddle player. She was totally badass and an insanely good player.


our view at dinner
the personalized menu
filet with scallops (left), creme brûlée with cranberry pistachio shortbread (right)

The Signature Room Restaurant

So, I think at this point it’s safe to say that good food and one fancy restaurant per trip is quickly becoming a tradition among my friends and I. This restaurant, located on the 95th floor of the John Hancock Building in downtown Chicago, had an amazing view. This was our “fancy” dinner of the trip and it was definitely fancy. As I said, the view was great. We had a table with a good view of the water and Navy Pier so we were able to watch the sun set and the ferris wheel on Navy Pier light up as we ate dinner. Because we were celebrating a special occasion, I was also able to arrange for special menus to be printed for our party when I made the reservations.

That was a lovely surprise for Julia, who had no idea and was not expecting to open her menu to see “Happy Birthday Julia” printed across the top. After we ordered, our waiter took the menus and rolled the pieces with the birthday note on them into a scroll so she could take them home with her. If you specify when you make the reservation that it’s for a special occasion, the restaurant will send you a list of special add-ons that you have the option of choosing from if you wish. Tabitha and I talked it over and while some of the other things (like flowers, dessert, or chocolate-covered strawberries for the table) were nice, the menus seemed like the best and most special option for us. And, while I feel it goes without saying, the food was pretty damn good here too. We definitely enjoyed our meals.

What are some cool places you like when in Chicago?

❤ Rachel




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