I just got home from such an epic weekend in Chicago celebrating my older sisters Bachelorette! My sister was a 2020 bride that has had to reschedule her wedding multiple times as well as her original Bachelorette. She is also a healthcare worker that has been through it this past year, so my younger sister and I really wanted to make this Bachelorette weekend PERFECT for her!
My older sister Gwen lives in Chicago and thought it would be easiest given the circumstances to have her Bachelorette weekend there vs Charleston, SC, which was the original idea. We found an AMAZING VRBO in Wriglyville that easily fit all 13 guests and it ended up being the perfect spot. I highly recommend if looking in the Chicago area! LINKED HERE.
Due to a lot of COVID restrictions still in place in Chicago (all 13 of us were/are vaccinated just an FYI!) we decided against any big group outings or dinners. It was really nice to actually just hang at the house and play games, laugh and have fun! We planned a few surprises throughout the evening like matching Pajamas, a professional photographer to capture memories (Jules Kennedy Photography – highly recommend in Chicago area) and pizza/a karaoke party!
LINK TO CANVAS TOTE MAKEUP BAGS – HERE
*I linked below all of the decorations we used for the weekend! I highly recommend this particular balloon arch over paying a company to come and make one! It was super easy to put together and use. I also recommend the Piggy Balloon Pump. It saved us from having to blow up every single balloon – TRULY AMAZING and probably the #1 thing you need to purchase!*
SHOP EVERYTHING BELOW
Saturday afternoon I put together a fun little pop up shop with Kendra Scott! The Kendra Scott team came to our Airbnb and set up on our outdoor lawn and it was the most beautiful day! I also always love planning a non-drinking activity, especially for a bachelorette weekend, and this was perfect! The girls loved getting to pick out jewelry for the wedding and get to do something different from their everyday. The Kendra Scott team was also LOVELY to work with!
Due to everyone being vaccinated we also planned a super fun Chicago Trolley to take us around. I had never done one before and it was a BLAST. We made one stop at an outdoor bar where we could spread out and drink safely (max 6 per table currently in Chicago). Otherwise we mostly stayed on the Trolley danced and had fun! They picked us up and dropped us off back at our VRBO.
For that night we hired a private chef to the VRBO to make dinner! Honestly avoiding big group dinners as a whole was the best idea. It made the weekend so much less stressful and cheaper. We did a taco bar (chicken & veggie) and it ended up being $30/per person – which was AMAZE. We hired a chef recommend to us by our VRBO owner – if you would like her email DM me!!
Overall it was such an amazing weekend and I highly recommend Chicago as a Bachelorette destination!

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