Alex’s Chicago Bachelorette Party

I can’t believe my best friend Alex’s wedding is just a few months away!

I am honored to be joining her sister in standing as a co-Maid of Honor (she doesn’t like the word Matron, so we are both deemed Maids of Honor) on her big day come late December.

Taking advantage of a three-day weekend, we planned to whisk our bride-to-be and the other bridesmaids away for two and a half days of celebrations and pre-wedding shenanigans.

When searching for a destination, we wanted somewhere close enough to drive from the Detroit area that was safe for a group of girls to walk, shop, dine, and explore the city. Chicago sounded perfect, and we tried our best to keep the whereabouts a secret from the guest of honor. She absolutely loves the city, and tries to get over there as much as Scott and I do!

Before our arrival, the only thing our bride was in the loop on was a modified version of the invite I put together several weeks before:

(I created this image using Canva. You can put similar posters like this together to download online using the free software. I also use PicMonkey for similar graphics!)

Taking advantage of the (long) holiday weekend, we set out for the five hour drive to Chicago from the Detroit area around 11 a.m. Saturday. We didn’t hit too much traffic on the way, and had plenty of time to check-in and decorate the hotel room once we arrived.

Thanks to a generous family member’s elite status, we got a great deal on a hotel room at the Chicago Marriott Downtown right on Magnificent Mile. It was conveniently located on the main strip of the shopping and dining district, which helped us with costs getting to and from our destinations throughout the weekend!

Since we all drove together, we sent the bride down to the hotel bar for a quick toast with a bridesmaid while the rest of us went to work decorating the room. I purchased a Bachelorette Party sign and streamers from Party City…

Ordered a set of bridal party tattoos from the GoldTinselShop on Etsy, found light up rings (that turned out to be a hit for keeping each other in sight while going out!) at Party City, and picked up the boa (from the Halloween section – go figure) and bride-to-be sash from Michaels.

I did, however, want to jazz up the sash a bit. I found a strip of gold stoned ribbon, a big white bow, and had fun decorating with a glue gun. I also found a set of different colored wine tumbler glasses on my way up to the register and couldn’t pass them up!

The sister of the bride and my planning partner in crime, Dana, ordered her this customized bride wine glass from Twinkle Twinkle Lil Jar. (So cute, right?) Before long, the bride was knocking on the door and we were all ready to get the weekend started.

After months of planning, we were so excited to be in the room and take in the view!

We popped a bottle of champagne and lounged around in the room to discuss things we wanted to do while in the city for the weekend. We had the night ahead of us already planned out, but everything else was left free to be able to see what the bride wanted to do and be able to go with the flow.

Cheers!

We spent a couple of hours walking around the shops on Magnificent Mile, then walked back to our hotel room to get ready for the big night out. The group of us sported little black dresses (and rompers) and our bride-to-be was decked out in white with a pair of beautiful grey suede heels she picked up earlier that day.

Watch out, Chicago… here we come!

We originally planned to dine at The Purple Pig, but they don’t take reservations and you have to put your name on the waiting list in person. After hearing it would be over a three hour wait, we postponed those dinner plans until the next day and found a great restaurant across from the hotel called Bandera.

Bandera is a fantastic dinner spot for anyone looking. Dana had previously visited one in Scottsdale and raved about the menu and atmosphere of other Hillstone restaurants. Bandera is on the fancier side, and might be a dinner you leave the children at home for to enjoy with a group of girlfriends or on a date. I loved the big city feel to the space and live jazz music playing throughout our meal!

We put in our names in and had a quick thirty minute wait for a table for five. Not too shabby for a last-minute decision on a busy Saturday night! We enjoyed a round of artisan beverages at the bar and immediately started drooling over the menu.

If you ever get the chance to visit, you have to order the Iron Skillet Cornbread. It has just a kick of jalapeño spice to it and is seriously the best I’ve ever had at a restaurant. So good.

Wanting to keep it light (and knowing there were late-night snack options available if we needed them later on), both Alex and I ordered the Macho Salad with roasted chicken, mixed greens, avocado, dates, goat cheese, toasted almonds.

It was good, and surprisingly filling enough to skip dessert! Don’t worry though, we had plenty of sweets throughout the rest of the weekend. After the day of travel and afternoon of shopping, half of our group ordered coffees and we all geared up for the night ahead!

We had a little bit of downtime before our next outing, so we walked back to our hotel room and showered our bride with a panty party I’ll share more of, along with other party games tomorrow.

By 10:30 p.m., we were all set and ready to Uber over to our next stop, ROOF, a rooftop bar at The Wit Hotel.

ROOF is easily becoming one of my favorite late-night spots in Chicago. I visited once before, and instantly fell for the view of the city and variety of music. Scott’s best friend (who lives in Chicago) helped me put together a special table reservation for our party, and the group of us had a blast dancing the night away!

We arrived back at our hotel in the wee hours of the morning and my cheeks hurt from laughing more than my feet did. Our weekend celebrating the bachelorette was off to a great start!

 

Stay tuned for a recap of Day Two coming soon…