For my birthday this year my boyfriend and I took a quick weekend trip to Chicago. We’ve both visited the Windy City before, so making an itinerary was much easier, and since I was feeling under the weather we decided to have a slow-paced weekend. I thought I would take a few moments and share the highlights of our trip.
Where We Stayed:
We stayed at the Silversmith Hotel located in the historic Jewelers Row District, which I didn’t realize until I noticed we were surrounded by jewelry shops. The location was amazing, with only one block between the hotel to Michigan Ave and Millennium Park. The hotel had a mix of Art Deco and Modern decor which gave it a distinct personality. When we first arrived on Friday evening, the Adamus lounge on the main floor was buzzing. We didn’t get to enjoy the space, but it looked very cozy with individual nooks and booths.
We stayed on the top floor which is always nice, facing the L train…which might be a sound issue for some, but since we have both lived in NYC I barely noticed it. I enjoyed that our Premium King room had a separate sitting area from the bed. I never spend that much time in hotel rooms when traveling, but its nice to have a dedicated space to unwind after a long day. The bathroom was quite large and came equipped with Molton Brown toiletries and a very cozy bathrobe.
Where We Ate:
I’ve noticed that over the years the highlight of any trip for me is the food. I am lucky that my boyfriend and I have similar tastes in food and he is always great at picking restaurants that don’t disappoint, so I let him take the lead on scoping out spots to check out in Chicago.
The Gage
We had some recommendations from several friends of spots to consider for my birthday dinner, but reservations were hard to come by and the earliest we could find was 9:30pm. Around 7pm we abandoned our reservation for The Gage restaurant conveniently located on Michigan Ave around the corner from our hotel. We were pleasantly surprised when we only had a short wait and we were able to grab a drink at the bar before being seated.
For our first course we tried the Oysters and Roasted Beet Salad, followed by a second course of their Fish of the Day Red Snapper and Seared Scallops. I was so thrilled when I could actually eat a dessert off the menu, especially since it was my birthday, and we devoured their Chocolate Almond Candy Bar. Everything we ate was not only beautiful, but so delicious! Coupled with the candlelight, our cozy table in the back, and the overall feel of the space, it made for a great birthday dinner spot.
The Purple Pig
On Saturday we had a definite plan for dinner. My boyfriend had his eye on going to The Purple Pig, and since they don’t take reservations, we knew to prepare for a wait. A few weeks before our trip I called the restaurant to get an idea of the average wait time for dinner on a Saturday night. We were quoted 30min to 1.5hrs, so we planned on eating a late lunch and heading right over from our Second City show to put our name on the wait list. It ended up being right at the 2.5hr mark, but we spent the time grabbing a snack at Sweetgreen and browsing in shops nearby.
The menu did not disappoint. Every dish was interesting and tasty, and I appreciated that everything on the menu came with a wine pairing recommendation. When I cook for myself I usually go for vegetarian or vegan recipes, but my boyfriend is a big pork lover and you can’t not try a pork dish at a restaurant named after the animal. We started out with the Smoked Pork Tongue and Charred Cauliflower paired with Vermentino, and then moved on to Octopus a la Plancha and their famous Milk Braised Berkshire Shoulder paired with Godello. The restaurant doesn’t have a dessert menu, but we had already stopped and grabbed some macaroons at Alliance Patisserie to munch on later that night.
Cindy’s
After working many brunch shifts in NYC and not getting a lot of opportunity to enjoy the cool spots the city has to offer, I am now an avid brunch enthusiast. So when my boyfriend suggested Cindy’s at the top of the Chicago Athletic Association Hotel for Sunday brunch it was a definite YES! What’s not to love about a bright rooftop with a cool vibe, beautiful views of Millennium Park and brunch?! We weren’t able to snag a reservation at the last minute, but we did put our name down for the cancellation list and arrived to line up before the restaurant even opened. I was feeling a bit crunched for time since we hadn’t yet checked out of our hotel and we weren’t given a time frame of expected wait to sit at a table. I was fully expecting to wait upwards of an hour, but after grabbing a drink at the bar, we were lucky enough to grab a counter table big enough for the two of us.
We munched on the Farm Egg Omelette, Seasonal Fruit Bowl and because apparently we didn’t get our fill of pork the night before, a side of bacon. I eyed our neighbor’s pancakes with sadness because they looked amazing, but unfortunately my gluten allergy wouldn’t let me eat them.
Kizuki Ramen
We popped into this ramen chain in-between secondhand shopping and I’m still thinking about it! I ordered the Spicy Ramen in medium spice with their gluten free yam noodle. It was the perfect dish, along with a few cups of complimentary green tea, on cold day to have while fighting a cold. I will definitely be checking out some ramen spots near me!
Where We Visited:
The Art Institute of Chicago
The Art Institute of Chicago is a must see when visiting the city. They have an impressive collection of works from iconic masters. I was pleasantly surprised they have a few spots to stop for a bite to eat or recharge with a coffee or tea, and a fun museum shop to pic up some souvenirs. We weren’t able to check out the entire museum, as it has so much to see, but the highlights for me were the Impressionists and the Arms & Armor collections.
Millennium Park
When you finish your visit at The Art Institute take a stroll through Millennium Park. Take a fun picture with the famous “Bean” sculpture, get your feet wet at Crown Fountain, take a stroll through Lurie Garden, grab a bite at
Park Grill or check out a show at the Jay Pritzker Pavillion.
Second City
For something fun and different, we decided to check out a comedy show. And what better place than the legendary The Second City. We bought tickets for their The Best of the Second City show and enjoyed the sketch and improv comedy. The venue was small and cozy with no bad seats in the house, and you were able to order snacks and drinks during the show. It was a great way to unwind during a busy siteseeing day.
Buffalo Exchange/Crossroads Trading
Secondhand shopping was high on my list of to-do’s in Chicago, so we dedicated our last afternoon in the city to checking out Buffalo Exchange and Crossroads Trading, both I’m familiar with since they also have locations in NYC. You never know if you will have success when you are secondhand shopping, but I was lucky enough to find two short-sleeve shirts and a bodysuit.
Chicago was a great city for a short weekend trip and I’m so glad we were able to get away for my birthday this year. I definitely will be looking forward to making another trip, but hopefully in the summer! I’d love to hear your fav Chicago spots to keep in mind for next time.