THE ULTIMATE ANNIVERSARY WEEKEND IN CHICAGO

Last month, in early December, Will and I celebrated 5 years of marriage together. We talked about how we wanted to do something really special and decided we would travel to Chicago to celebrate! We have always been curious about this major city in the Midwest + there were so many festive things to do during the month of December for the holidays. We figured it would be super romantic to spend the weekend in the cold windy city!

We had plans to visit super touristy spots and to try to see most of what the city had to offer— but we also were set on relaxing and having an easy going approach to our weekend. Chicago definitely has the some of the best restaurants, things to do, and hotels!

WHERE WE STAYED

THE BLACKSTONE HOTEL

We had a few accommodations in mind, but ultimately decided to go with Will’s pick of The Blackstone Hotel. This hotel was the perfect choice! It's located on Chicago's Cultural Mile and right down the street from Millennium Park and Lake Michigan. We had a perfect view of Grant Park, which made for an amazing view during sun rise!

The Blackstone is also known as the “Hotel of Presidents” and has hosted US presidents, foreign dignitaries, political and mob exchanges, actors and more! FUN FACT: It hosted Al Capone every time he was in the city. He even had his own barber chair where he used to get his grooming!

Upon arrival we were treated to complementary glasses of Champagne to begin our celebration after we checked in! Our room service was phenomenal—anything we needed at mostly any hour was accessible to us. We also loved the holiday decor and grand fireplace in the lobby. We were able to enjoy a few handcrafted cocktails while listening to live music played by an acoustic guitar player almost every night we were there. So relaxing.

WHERE WE ATE

WILDBERRY PANCAKES & CAFE

On our first morning in Chicago we ate breakfast at Wildberry Pancakes & Cafe. Our hotel was only about a 7 minute drive away. With an Uber ride, we were able to get there in no time. Located right across from Millennium Park, this cafe features an extensive menu offering breakfast fare, brunch, lunch, and more. While we waited for our table I recognized Erica Campbell of Gospel duo Mary Mary and after waiting for the right time, I walked over to say hello and introduce myself!

If you have a sweet tooth, order the Signature Berry Bliss pancakes! We were there pretty bright and early right at about 9am and although it was pretty busy we only had about a 15 minute wait time.

UMAI JAPANESE RESTURANT

We were in the mood for Japanese food for dinner so we stopped by Umai for sushi and ramen. The ambiance in Umai made for a intimate & cozy atmosphere with it’s modern lofty feel and dim lights. For an appetizer we had the Hamachi Kama (Grilled Yellow Tail Collar with sea salt. For dinner I ordered the Spicy Roasted Garlic Chicken Ramen and Will ordered 2 rounds of sushi.

THE ALLIS AT SOHO HOUSE CHICAGO

Saturday we headed over to Chicago’s West Loop and had brunch at The Allis At Soho House. The Allis is a must-visit locale. The Allis’ chic décor of velvet couches and marble tables makes for the perfect setting for a date or meeting over afternoon tea. The concrete ceilings are lined with Parisian chandeliers. I had the Allis Breakfast and Butterscotch Hot Toddy. This drink was perfect. It was so cold outside and this place made for the perfect escape to get cozy.

LOU MANALTI’S

Later Saturday evening we wanted to finally try the infamous deep dish pizza that Chicago is known for. It was so cold that evening, but we were bundled up pretty nicely and didn’t mind the 7 minute walk to the restaurant from our hotel. We were in for a 30 minute wait. As we waited and talked in the lobby we recognized a couple that we had met earlier that morning in our hotel lobby. We all ended up getting a table together and more of the couple’s friends came in to join us! It was pretty nice and kind of felt like a big family laughing and exchanging stories about where we were from over an Italian feast.

Will and I both underestimated the sizes of our pizzas. Keep in mind that these aren’t your averages sizes. Because I love veggies so much— I would highly recommend the ‘Lou’—- a spinach mix (enhanced with garlic, basil & onion), mushrooms and sliced Roma tomatoes covered with three cheeses, on a garlic Buttercrust. Too good!

We all decided to carry our party over to the Hilton Hotel (which was another short walk—as matter of fact right across the street from our hotel). We ordered more cocktails and sat by the fire near the hotel bar. Myself and the ladies had girl talk while our guys carried on with their own convo. We didn’t get back to our hotel until after Midnight. It’s so funny. Will and I always talk about how we end up almost always meeting other nice couples on vacation. Young or old we always hit it off with new people and end up having a great time naturally.

GARRETT POPCORN

This was by recommendation of one of our Uber drivers. Side Note: We found it super refreshing that the locals were so friendly. Once people heard we were visiting for our anniversary, they were all really excited about telling us the ‘must sees’ of Chicago. We made our way over to Garrett Popcorn to take a midnight snack back to the hotel with us. I got an assortment of flavors. I tasted the ‘Chicago Mix’ and Will liked the Cashew Caramel Crisp. We weren’t exactly wowed by the popcorn but we couldn’t complain too much about it.

WHAT WE DID

GRANT PARK + CLOUD GATE

You can’t plan a visit to Chicago without visiting Cloud Gate in Millennium Park. This was one of the things at the top our list of things to do! We ended up Ubering over to Millennium Park after we visited the Chicago location of my husband’s job. It was so cold this afternoon, but we enjoyed every minute of the park. A nice older couple ended up taking our photo and even suggested a few more places to see in the city. We decided to walk back to our hotel since it wasn’t too far but our phones ended up dying and we got lost. We walked to a Starbucks nearby and no one seemed to know where our hotel was located. Instead of wandering out in the cold, we charged up inside over a cup of coffee.

SKYDECK

Sky Deck Chicago was actually number one on my list of things we must do! The Skydeck is located in the Willis Tower- which is the tallest building in the Western Hemisphere! There is a glass floor balcony that extends 4 feet out so you can look over the city. It's a crazy feeling because you're 1,353 feet up in the air and it feels like you're floating! I wasn’t nervous about heights until we actually reached the top! The experience was wild. Will didn’t even want step out onto the glass once we saw how high we were. I decided to go for it! The minute I took a few steps out I had to ask myself why I was doing this! I’m surprised I was able to get the photos below because I was shaking so bad! My palms were so sweaty! Sitting down on that glass was a thrill to remember! What’s awesome is that because of the time of year we went, we didn’t have to deal with the super long lines we had heard about!

SHOPPING IN THE CITY

The plan was to head to the Christkindlmarket to drink mulled wine and Raclette. Unfortunately the market was jammed packed to the point that it was uncomfortable to even walk through the market. We ended up stopping to purchase a Stein for Will and after just walked over to the mall to do some light shopping.

WNDR MUSEUM

The WDR Museum was the absolute best. It’s an immersive art museum experience located in the Chicago West Loop. We called this our ‘Day Date’ on our last afternoon in Chicago. We took so many photos. My favorite part of the museum was definitely the Yayoi Kusama Infinity Mirror Room! After the museum we walked just down the block to Warm Belly Bakery for coffee and treats!

WARM BELLY BAKERY

Chicago is such a fun city and there is so much to do. It's guaranteed to be a good time no matter what you do. Celebrating our Anniversary here was an excellent choice. Many will shy away from the cold, but we embraced it and it was actually really romantic. Have you been to Chicago? How was your experience?