Travel With Me to Chicago - My First Experience as a Groomsman in a Wedding!

Since the day my best friend from college, John, got engaged to his fiancé, Tresa, I was pumped for the wedding! I knew it was going to be a special event, because when the Sears family does something they do it right!

@Morganannwood and I departed from the airport Thursday morning and arrived shortly after 6am. She looked a lot more presentable than I did, per usual.

Whenever we travel together, it doesn’t matter if we are going for a week or a weekend, her bag is always too heavy (It must be the scales at the airport). After shifting some stuff around her bag was good to go and we were off to the gate.

After a quick flight to Charlotte and a 45 minute layover we were off to Chicago, where the wedding and events would be held.

By 11am we touched down in Chicago and we arrived to the hotel shortly after 1pm. My other best friend from college was at the hotel with his fiancé waiting for us to get checked in. After getting settled, the four of us were starving.

Rosemont

Hofbrauhaus

We called an Uber and were off towards downtown Chicago. We ate lunch at Hofbrauhaus in Rosemont. This was my first time eating at this restaurant. The beers were good and the food was filling.

Big 10 Headquarters

I was completely unaware the Big 10 headquarters were in Chicago (Rosemont). After walking past it on our way to lunch we had to stop in and see what it was all about. They had interactive games for us to play and statistics about the conference in different sports. Best of all, we got in for Free.99.

Fashion Outlets of Chicago

Morgan is a shopping fanatic and if I told you how many separate times she came to this outlet you wouldn’t believe it. I lost count after the first 3 times. After salivating over this ring for nearly an hour, Morgan said she “had to have it” and it eventually ended up coming home with her.

Untitled Supper Club

If you have traveled to Chicago and haven’t gone to dinner here, I highly suggest it. Thursday nights they have burlesque type show that was unbeatable. The food, cocktails, and ambiance were superb!

Magnificent Mile

Friday was a leisure day for us until the rehearsal dinner so we decided to explore the city. After a 30 minute Uber ride we landed in Millennium Park.

Cloud Gate aka The Bean

Like most tourists, this is a must see! I don’t think I have ever seen so many selfies in my life! After taking a few selfies of our own we were off to start walking down the Magnificent Mile.

I saw my first Nutella café. Shout out to all of the Nutella lovers out there.

I saw the Trump Tower with 0 protesters outside.

I saw this odd statute with Abraham Lincoln and this guy who I had never seen before. I later found it was Perry Como (still kind of unsure who that guy is).

John Hancock Center

A few friends strongly suggested going up to the top of the John Hancock Center. On the 96th floor, they had a bar you could go get a drink at and overlook the city! The views were stunning!

They even had their own specialty Knob Creek.

Saturday aka John’s Wedding Day aka The Big Day

All of the groomsmen got together early in the afternoon on Saturday to start getting ready for the wedding!

Matt and I were looking fresh in our tuxedos with our purple tie and vests.

John Sears is literally “The King of Carpet” and there was no better way for them to give out the table seating requirements than on a carpet sample. This was genius! It even matched our tuxedos.

The Groomsmen had a small poker game prior to the wedding that I did not participate in. It was fitting that the Groom won the poker game. This was a hand he hit earlier in the night - Quad Queens.

The wedding itself was incredible! Both John and Tresa looked amazing! This might be my favorite shot of the night from them.

From the maid of honor speech to the groomsman speech, both of these could not have been better. I still can’t believe the reception had an open bar for 6 hours – some of us took FULL advantage of that, while others took advantage of the Hot Dog stand. How bad@$$ is that to have a legit hot dog stand at your wedding! Well done the Sears/Lentzen families.

Sunday – The travel day

Going home always seems to be the longest day on vacation. Our first flight did not leave until 5pm from Chicago, so what do you think we did to kill some time? If you guessed going to the Fashion Outlets of Chicago…. You are correct! My boredom was kicking in and I saw a mannequin at the front of Bloomingdale's and I had to take a picture with her.