How to: Plan a Bachelorette Party in Chicago

So along the lines of unsurprising confessions, you guys can probably tell (if you don’t know me personally) that I am a planner.

I plan everything. (And then I usually blog about those plans.) From outfits, to vacations, to haircuts, to how I’m going to spend my time off. It’s a sickness, but I have embraced it as a part of my life that isn’t going anywhere.

And in some cases, it’s even a blessing. Take, for example, the time my best friend was getting married and needed someone to plan a bachelorette party/bridal shower for about 25 of her closest girl friends from all over the country in a state about 1,000 miles away from me.


Honestly, I was thrilled to do it. Annie is one of my oldest, dearest friends, and I’m so excited to be in her wedding in September. Her sister is her maid-of-honor, but since she’s only 19 and swamped with school and choir and other responsibilities that come with being an active college student, I offered to take care of the party planning.

And let’s be honest, my life makes more sense when I know what is going on (in detail), and what better way to know what’s happening than to plan it yourself? (Spoken like a true control freak. sigh…)

Obviously, there were some initial roadblocks. For one, the party would take place in Chicago, and I live in New York. For another, we were talking a fairly substantial group of girls (it ended up being about 25 people total). Fortunately, Annie has another bridesmaid who lives in the area who was on-hand to help with recommendations.

Here’s where we stayed, what we did, and how it held up (and a lot of photos that I stole from Susan’s Facebook album…ha):

Where we stayed: The Wyndham Chicago Downtown Hotel

{me preparing to do Annie’s makeup…Lauren doing…something ha}

Seven girls stayed in the hotel, so we booked two rooms. The hotel was nice enough to give us adjoining rooms, so we just propped open the doors and turned it into a giant suite. No complaints about the hotel! It was nicely located, fairly priced, and it even had nice soaps and stuff.They also let you order pizza and have it delivered to your room at two in the morning. Which might be a common occurrence in hotels, but this was the first time I had done it and was pleased to find there weren’t any issues.

Final grade: A

Where we ate: Cafe Ba-Ba-Reeba

{JAB reunites for dinner!}

One of Annie’s favorite restaurants in Chicago, Cafe Ba-Ba-Reeba was a natural choice for dinner. Plus, it’s one of the few places in town that could accommodate our large group. We could have booked a private room, but we opted for a standard reservation (two tables) to save everyone money. Everyone ordered about two tapas each, and we got four pitchers of sangria for the table. The price ended up breaking down to be extremely reasonable (about $25 per person…we were really glad we hadn’t sprung for the private room), the service was great, and the food (and sangria) was delicious.

I also recommend a quality light-up sash for the bride at all times.

Final grade: A

How we traveled: Chicago Trolley & Double Decker

{the passersby were big fans of us}
{so much trolley excitement}
{craziness…this photo courtesy of Nick Miller :)}

OK, I just need to say this: If you’re planning a party for a group in Chicago, get a trolley. We had so much fun aboard this thing. Plus, we got to visit a few different bars without having to hoof it around town in heels. (Plus, you can bring drinks and whatever you like on the trolley. Need I say more?) Our driver, Erica, was super sweet and took great care of us. Highly recommend!

Final grade: A+

Where we partied: Howl at the Moon

{reaching up and pulling it down was Annie’s signature move}

We stopped at a few bars on the trolley (I remember one was called Cans, but another girl planned the stops and I can’t remember the name of the second bar), but afterwards we had a reservation at Howl, a dueling piano bar. It’s a popular spot for brides-to-be (I think we counted 17 bachelorettes total that night), so it’s of course a bit cheesy, but definitely a great time. Our reservation (which cost about $25 per person) allowed our group to cut the line, paid each person’s cover, got them one drink, and got the bride a stage call. Meaning the lovely Annie was serenaded (I believe she picked “Party in the USA.” Because she’s classy like that.) in front of everyone. We danced, we sang, and we completely lost our voices. Fun times for all.

Final grade: A

What I’m saying is, the night went perfectly. No one got lost, there was zero drama (despite being a group of about 25 girls…), and everyone had a great time. Definitely makes the four(ish) months of planning all worth the effort!

Sunday afternoon, we had a little shower for Annie at her friend Kelly’s apartment. (For food, I went with Panera bagels, a fruit salad I chopped up that morning, and cake pops made by another bridesmaid, Linda. It was all a hit.) Annie got a few presents, and we lounged around recounting our favorite moments of the night before. A pretty good Sunday by any standard.

I am just so relieved everything went so smoothly and everyone had a great time! Planning a party for that many people (from half way across the country) is a bit stressful, but Annie had a lot of fun, so it was completely worth it.

{the lovely bride and me}

Have any of you ever planned one of these? Any disaster stories to share?

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7 thoughts on “How to: Plan a Bachelorette Party in Chicago

  1. You know what’s funny? I’m actually planning a bachelorette party in Chicago right now but when you asked for my help with this, which I know I hardly provided, I didn’t realize I’d be right behind you on this… maybe some of those suggestions will be repeated 🙂

  2. Weekend in totality – A+++


    I still have no voice and my body is sore from too much partying.

  3. My partner and I are starting to do some salon evenings that might be suitable for bachelorette parties- just testing it out for now. What do you think? Thanks!

  4. Do you remember about how much it cost each girl to chip in for the trolley? I’m planning on doing the same thing for a bachelorette party this June for about the same size group of girls and want to let them know what to expect to pay. Thanks!

    • The total cost was $530 for three hours, and I had about 24 girls chipping in, so it ended up being really reasonable. We brought our own drinks to have “on board.” Hope that helps!

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