Chicago Anniversary Weekend

Every year my now fiance and I travel for our dating anniversary, February 12th. My school system always has an inclement weather day around that time, so we turn it into a 3-day adventure. This year, he chose Chicago as our destination and it was a fantastic weekend despite the cold.

Accommodation:

I went back and forth between hotels and landed on Embassy Suites Chicago Downtown Magnificent Mile due to the great price, location and free breakfast that was included. The room itself was very spacious and the location was prime since we could walk to everything. Unfortunately, the free breakfast was crazy. The line every day was very long and we were fearful they were going to run out of food. It was also very difficult to find a place to sit. I booked through hotels.com with my Capital One Venture Card so I could get 10 points per dollar I spend. If you sign up for hotels.com rewards you also get a night free after 10 nights booked. The only thing to be wary on is they send a lot of emails. Make sure you update your settings so you don’t get spammed.

Transportation:

The majority weekend we took either walked or took the CTA (Chicago Transit Authority). It’s very easy to navigate and very affordable. We took the Midway orange line and changed at Roosevelt to the red line and got off at Grand. When we didn’t use the train we walked to many of the local places we went to. Chicago does have Uber and Lyft readily available and the prices are very comparable to Atlanta’s.

Day 1:

Millennial Park/The Bean:

Since it was a Friday morning we thought we would hit the touristy spots at the beginning of the day. Walking from our hotel to Millenial Park took about 15 minutes. On our walk, you get to take in the stunning Chicago skyline. During the wintertime, there aren’t any Architecture Tours available, but I found the perfect solution. The WTTW App allows you to get all the historical information on a regular tour but on your own time and phone. The best part is this walking tour is free.

The park itself gives you gorgeous city views and of course, you have to take a picture with the iconic Bean. Did you know that the iconic sculpture is actually titled the Cloud Gate? Since it is such a large attraction, they actually have cleaners who come twice a day to shine it. If you are a big germaphobe, you might want to keep your hands off in this situation and stick with a mesmerizing photo.

Art Institute of Chicago:

While walking through the park we came upon this Art Institute and it was not originally on our list. We are normally not big museum people, we prefer activities but I’m glad we came upon this place. We were thoroughly surprised by this institute since it had a blend of many different types of art and exhibits that were very engaging. It was worth the price and I would recommend even if you weren’t an art person. We spent almost 2 hours in the museum and could have spent longer if we didn’t have other plans.

Small Cheval:

We headed a little northwest of the city to meet a friend and had burgers at the most amazing joint. Any restaurant that has a limited menu always seems to be 100 times better and this was no exception. I got a simple burger and fries with a chocolate shake and it all melted in my mouth. They have a sister restaurant called Au Cheval that is a little bit more upscale and has a winder menu. It would be a perfect date night spot inside the city.

Revolution Brew Pub:

Right down the street from Small Cheval is a great local brewery that we spent a few hours at. I loved that they also had wine options for non-beer drinkers. It was a very wide open space, a great vibe and it had this delicious parmesan popcorn.

The Vig:

This was a dinner reservation that I picked out before we left for our trip because it came highly recommended. Their 1950s decorated restaurant paired with curated cocktails and simplistic but delicious food was to die for. We were still super full from the burgers we had earlier, so we got a lot of smaller plates. We each got a chicken bao bun to start. I paired it with their fruitful “Caio Ciao Amore” cocktail. To make sure I didn’t get too hungry for the rest of the night, I ordered the Royal Isabela Roasted Corn salad and it was fantastic. I normally do not like mushrooms in a salad but these were wonderful.

Second City:

One of the top things we wanted to do in the city was experiencing one of the best comedy shows in the country. A lot of famous and great comedians have come through this theatre as up and coming artists. What I love most is that they have multiple theatres inside their locations. You can choose between 3 completely different types of shows. We chose a show called “Algorithm Nation or The Static Quo” and it was a mix between planned skits and improve. It was hysterical. Shows book up months in advance, especially on a Friday or Saturday night, so make sure to buy your tickets early. Also, get to the theatre early because seating is first come first serve to get close to the stage.

Signature Room at 95th:

We were wiped out after the comedy show at the end of the night so we headed back to the hotel. If you are a night owl, many of our friends recommended going to the top of the John Hancock building to grab a drink. Seating is on a first come first serve basis, and they do have a nice dress code (no flip flops/shorts/etc.). It offers stunning 360 views of the city and affordable drinks.

Day 2:

Hutch American Cafe:

We found this great brunch spot that we met some friends who were in the city for the weekend. Hutch American Cafe takes reservations and is very affordable, including $5 mimosas. I got the chilaquiles which was very different from my normal brunch choices but I devoured it.

WNDR Museum:

The WNDR museum was all over social media and we got sucked into it. It had an exhibit by the famous artist Yayoi Kusama which was a huge draw. It has many different colorful and interactive exhibits that were fun to experience as a group of friends. In total, we spent an hour in it, and 20 minutes of that was waiting in line for the Kusama exhibit. For the $32 price and short experience, I wouldn’t recommend going a second time.

Bar Siena:

After our WNDR museum experience, we decided to head down the street to the local bar scene. The west loop area is known for its food and drinks. With an industrial throughout, Bar Siena was the perfect place for an afternoon drink. I got the Number 5 cocktail which was very refreshing and delightful. My friends got other cocktails and beers as well and enjoyed them all.

Momotaro:

Food is a love language of mine, and sushi is part of that love language. Momotaro was recommended as the best sushi in town, but you have to put a reservation in at least a month out. We didn’t put a reservation in time, but when the doors opened right at 4:30 we were able to grab a seat at the bar. The sushi is pretty reasonably priced, but the hot dishes are expensive for their portion sizes. We each got a sushi roll, and one of the rice bowls. We got the Yakatori Don bowl and the soft poached egg on top was delectable.

Blackhawks Game:

Since this was our anniversary weekend, my gift to my now fiance was tickets to the Chicago Blackhawks game. I have talked about this before in other posts that sports are a big part of our lives. We took the red line to State/Lake and then hopped on the Greenline to Ashland. It was then about another 15-minute walk to the center once you get off the subway. I discovered the best way to get a good and fair deal on tickets is by joining a season ticket holder’s Facebook page. Season ticket holders who can’t attend the game always sell their seats for face value and easy transfer.

Day 3:

Magnificent Mile:

Since our flight was in the late afternoon we didn’t want to go crazy our last day there. We slept in and walked the 2 blocks to the Magnificent Mile which is a street full of shopping. This strip of Michigan Avenue has every story you could imagine to hop in and out of on a cold day. We didn’t do a lot of physical shopping but it was fun to look around.

Deep Dish Pizza:

We couldn’t leave the windy city until we got the famous deep-dish pizza. I’ll be honest, I wasn’t feeling very well this morning so I wasn’t super hungry. We decided to go to Gino’s East. We ordered half a burger and fries (surprisingly very good) and half meaty legend pizza. It was a good pizza, but I wasn’t floored by it. As I said, I wasn’t feeling well so that might have impacted it.

Chicago is a fantastic weekend getaway at any time of the year. Do not let the cold weather deter you during the winter season because it is still just as fun. We loved celebrating our 7 year anniversary in the windy city and can’t wait to head to Los Angeles next year to celebrate our last dating anniversary. Have you been to Chicago before? If so, drop your favorite activity you’ve done in the comment section below.