Tips for planning a bombass bachelorette weekend in Chicago

Chicagoans love summer. To be fair, most people love summer, regardless of where they live, but Chicago is notorious for being at its best June through August. It’s beautiful here when it’s not freezing. There’s a lake and beaches and a world-class city and an overwhelming amount of things to do.

Whether you live here or are visiting, Chicago is a perfect place to go for a bachelorette weekend. Here are some planning takeaways from my recent “fling before the ring.”

Gross. Can we stop saying that?

Have fun!

Chicago so dreamy.

Book the hotel early and ask for extra towels

We stayed at the Crown Plaza in the West Loop. There’s a Whole Foods, Mariano’s, Walgreens and Starbucks all within one block, and the city’s main attractions are just a quick car ride away. For a few bones extra a day, they’ll valet park you in a hotel garage. It’s worth it. Trying to park down there for an extended period of time is a headache you can and should avoid.

Lots of mustache props. Not enough towels.

There were five of us staying in one room. That was fine. But I definitely didn’t predict how many towels we would need. Ladies love towels. While you’re at it, request a couple extra coffee packets too.

Reserve a table for brunch

This city is bumpin’ and if you’re trying to walk in for a table at a nice restaurant near Millennium Park on a Saturday morning, you’ll probably have to wait a while.

I love booking through Open Table. They’ll send you a confirmation email or text and the restaurants sometimes give you a call the day before to check on you/ give you some peace of mind that there’s really a table waiting with your name on it. Also, I’m a young-ish-person stereotype and hate calling and talking to real people; if I can book you online, I’ll choose your business first. Nails, hair, lunch reservations, doctor’s appointments, you name it.

We went to breakfast at The Gage, a sleek modern joint that has sweet and savory breakfast dishes worth swooning over. Our server recognized we were here celebrating something. (Definitely because of the sunglasses., baby! No penis accoutrements here. I don’t want a dick dangling from my head. Ever.)

Zero dicks.

When our server found out it was my bachelorette party, he brought us a celebratory glass of champagne and surprised us with dessert. A rhubarb and strawberry cheesecake with rhubarb sherbet. And a candle, because you gotta blow something on a weekend like this, riiiight? (My sentiment on the subject, not his.)

Day maker. Thanks, Archie.

Seriously though, his thoughtfulness kicked our day off better than I could have imagined.

Do get all touristy

I think there’s a hesitation to do the things all tourists do on weekends like this. Fair. Touristy things are often traps, like New Year’s Eve or Halloween parties: You exaggerate in your mind how freaking awesome the night is going to be only to find it’s kind of like any other party, but with more balls (dropping balls, popcorn balls, etc.).

You’ve set yourself up for failure.

But… tourist hot spots are big for a reason (except maybe Navy Pier… it’s disappointing, though Chicago magazine thinks that may be changing).

Chicago has so many amazing neighborhoods we could have explored, but I wanted my out-of-town visitors to experience some of the heavy-hitter attractions — the things that make Chicago Chicago. And, honestly, those are things I don’t do very often either, even though I live here.

We started in Millennium Park and just walked around. There were some great outdoor art exhibits, and walking through the flower garden across from the Art Institute was relaxing. We shamelessly snapped a million pics at the Bean.

Oh, and all that was free.

In Chicago, contrary to popular out-of-towner belief, you can get a lot in without spending a lot of money.

Video sculpture / fountain.

Bean. No balls.

The flower and herb garden across from the Art Institute is one of my favorite free things in Chicago. I dig the contrast of wild flowers with the soaring steel skyline.

Just walking through the cityscape was a great itinerary addition because it gave us time to hangout and talk, which is all I really wanted to do with my friends anyway.

Don’t over plan

Which brings me to my next point. Don’t over plan, lest you become a Clark Griswald type, shuffling your exhausted party from location to “fun” location.

On our Saturday in Chicago, we didn’t have any where we had to be at a certain time until that evening. This allowed us to stroll along Michigan Avenue and the down the Magnificent Mile at our own pace. We stopped into a few stores; Davids Tea (for a refreshing matcha cold brew) and Zara (for some honeymoon heels), what’s up?

Chicago’s Loop and Magnificent Mile are attractions in and of themselves. There was an art festival happening on the sidewalks. We hung out by the riverwalk. We got to sit in a Tesla. We watched boats go by from the bridge.

We gawked at this never-not-odd statue of Lincoln consulting the “every man.”

Things to do and see will organically present themselves here.

I did have one must-do on my to-do list. I wanted to walk to the Museum of Contemporary Art Chicago, one of many museums still on my Windy City bucket list. MCA offers discounts to teachers and students (two of my girls) and was hosting a Takashi Murakami retrospective.

So much color!

A caveat for visiting a museum in Chicago: Do your homework. The MCA has several floors and even more galleries. I knew we would be getting tired at this point, and while I didn’t want to over plan, I did want to make sure we were effective and saw the best stuff. We went in with the plan to hit up floors 3 and 4, then head out for food.

Floor 4 was dedicated to Murakami’s “The Octopus Eats its Own Leg.”

From the artist’s dark and muted early works about nuclear destruction and its psychological devastation…
To his disorienting, more recognizable colorful interpretations of painting and sculpture.

On floor 3 we explored the work of abstract painter Amanda Williams (who just happened to be there the same time we were and whom we all fan-girled over / stared at on the low).

Bricks from abandoned or foreclosed Chicago homes, painted in fake gold.

Williams developed paint colors that correlate with the Chicago South Side experience, like Flaming Hot Cheetos orange or Newport Squares teal. They evoke thoughts on how color so deeply defines Chicago and how segregated our neighborhood communities are. She then used this palette to cover abandoned and deteriorating buildings on the often-neglected South Side.

Why do we care about them only now that photos or pieces of these buildings are in a gallery? Now that they’re considered art?

How can you leave this place you’re visiting better than it was when you got here?

Thanks, MCA.

Eat Chicago pizza at some point

I mean, you gotta. It’s Chicago.

We walked over to Gino’s East after the MCA. Wherever you are here, there’s definitely probably a pizza place within walking distance.

Since Gino’s serves Chicago’s signature pizza, guests can leave their own signature on the restaurant walls.

Pro-tip 1: If you’re getting the true, original Chicago pizza experience (ie. deep dish), you’ll have to wait 45 minutes for it to cook. Get some apps, babe. And, perhaps this is sacrilege to the Chicago sauce gods, but the thin crust is awesome too, and you don’t have to wait as long or eat so much crust.

Pro-tip 2: Hot dogs and Italian beef sandwiches dripping in au jus are other famous Chicago foods you could substitute here. Just know if you put ketchup on your Chicago dog, a native will probably pick on you. Really. It’s a thing.

Just Uber

One of the life-changing aspects of living in Chicago, for me at least? Really solid public transportation. If I could take the L everywhere, I would.

(The L is for “elevated” and is the nickname for the subway trains here, although I call them “the trains” and often confuse people who think I’m talking about the Metra, the double-decker commuter lines that go out to the suburbs and the trains of which most people actually call “the trains.” A year and a half in and I’m still getting the lingo down.)

Chicago’s public transportation makes me more willing to go out and explore. I don’t have to drive or park or worry about a car. It democratizes getting around and makes nothing too far away. Chicago is physically huge, but the public transit makes it easy to get wherever you’re going. And I can read a book, answer emails or just dick around on Instagram while I ride. I love it.

However, it’s a little different when there’s a big group of you. I considered getting everyone in our group CTA cards so we could easily take the trains and buses around town, but doing that was more of a hassle than if we just split Uber rides (or Lyft, or cabs, or whatever rideshare you prefer).

Public transportation, while grand for daily life, isn’t really ideal if you don’t know how those in your group will handle what. You never know what you’re going to get on a train. It’s weird out there.

Plus, with those rideshares apps, you can know how long it will take you to get somewhere. It just makes planning easier and takes the stress out of traveling from place to place, especially if you don’t know the city very well.

That said, if you want to use the CTA, you can order passes and fares online. Use the Google Maps app day-of to see when the next train or bus is arriving and select the path that’s best for you group, with any combination of transportation types. It’s super helpful.

Support local art, music or comedy

We Ubered to Lincoln Hall for our Saturday night adventure.

Honey & the 45s. They played Lauryn Hill’s “Doo-Wop” AKA “That thing, that thing, that thaaa-aa-aaaaa-ng.” It was bachelorette party perfect.

Lincoln Hall always has a cool show happening and I love its upstairs and downstairs bars and seating. (We were there for Localpalooza, where a number of local bands played live and raised money for ALS research. Tickets were only $10 each.)

It’s also close to Kingston Mines, a fab, famous, dive-a-liscious blues club nearby that’s been around since the sixties. If you want to get sloppy and dance, that’s a fun place to go where your party-time will support local musicians and give you a taste of a sound that has helped make Chicago so famous.

Basically, the talent pool here is so deep that you don’t need to spend $100 on a ticket for talented entertainment. Check out Do312, Facebook and Red Eye’s Eat Drink Do to find cool, underground things coming up during your visit.

Rich Jones! He’s so good live.

Take photos at the lake

I don’t drink alcohol anymore and I guess that presupposed this aspect of our weekend. I don’t miss drinking but I do miss the camaraderie that can come from it. I was trying to think of something that could help create a similar bonding effect, but without the hangover.

A photoshoot with my friends seemed like an awesome solution. I wanted pictures that captured us in this moment of our lives. My female friendships have meant the world to me — they’re my OG love story — and it was worth having a professional take our pictures.

This was also a good solve for the fact that Justin and I aren’t having a wedding party and our ceremony is going to be super private. These photos are what we would have gotten at the wedding if we were doing something more traditional.

Our fantastic photographer, Jasmine Nicole, met us at Belmont Harbor. This location is special to Justin and I. We lived near here during our first year in Chicago together. And the lakefront is the gem of Chicago. Sorry, Willis Tower. It’s public and has the best views. Your photos could have a backdrop of the lake and the skyline. There’s parkland and Buddha heads and totem poles and beaches and all kinds of other interesting visuals you could pose in front of.

What I didn’t consider was that waking up and getting photo-shoot-ready for something that started at 8 am would be kind of shitty, hangover or not. Especially if you didn’t have enough towels (see point one) and needed to find parking.

Luckily we had solved for the latter the night before. You can order parking nearby online. We paid for a parking garage the night before and knew right where we were heading in the hectic, groggy morning. Again, totally worth it if you’re coming from out of town. It takes the stress out of trying to find a) a parking spot in Lakeview and b) a parking spot that doesn’t require a city permit.

As soon as we got started though, none of that mattered.

I now have photos with each of my best friends. The only props we brought were our heart-eye sunglasses and a quilt my mom made me for my sixth grade graduation, a nod to the other important women in my life who weren’t bachelorette party attendees.

Thanks, Ma.

Afterward we hit Broadway for lunch. Either direction you turn on to Broadway from Belmont is bound to lead you to a brunch spot. No reservations really necessary here.

I decided to do the photo shoot in East Lakeview because I know the neighborhood well and I knew we could find a lot to do if we wanted to hang out more. Some other great neighborhoods I considered for a lazy Sunday: Wicker Park (get your auras read!) or Pilsen (go on a thrift store and tamale binge) or you can’t go wrong just chilling by the lake in one of the parks or free beaches.

Just get here. You’ll find something incredible to do.

It’s Chicago <insert a million heart-eye sunglasses emojis>.

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