Friday, November 22, 2019

Pack Up + Go: Chicago! {Review}

For our anniversary this year, we opted to do a Pack Up + Go trip.  Friends of ours went on a trip and they highly recommended it, so I was like, why not?  Teh German was like, here's why not: you pay someone to plan your trip for you.. and I'm like, "EXACTLY."  Then he said, "We could just plan it ourselves."  And I laughed and laughed and caught my breath and laughed some more and finally choked out, "You mean, I could plan it."  He glared, my point was made, and then we filled out the form to start the process.

Our friends had explained the process and said that if they did another trip through Pack Up + Go, they would opt to fly somewhere instead of drive.  Makes sense, as we live in Charleston, SC and there's very few places worth visiting within driving distance.  So, we chose to fly.  This increased our budget.

Ultimately, we decided on a budget of $750 per person, which is $1500 for 2 people.  That's a lot more than I wanted to spend on a weekend, but I didn't have to plan it and adventures and shit, so fine.

If you're less interested in the process and more interested in the things we did, check out this link:

The process goes like this:

Pick your category.


Set your number of travelers and budget per person.


Fill out the info form.


Then you wait... for like, half your life or something to pass until it's a week before your trip.  And you tell everyone you know about this awesome trip you are taking, but you don't know where you're going and everyone is like DAFUQ?  Then you explain that's part of the appeal, but mostly the fact that you don't have to plan anything.

A week prior to your trip, you will receive an email with generalized information about your destination and your anxiety and excitement will start to build.


Honestly, I didn't bother to pack until the night prior because I wanted to wait for the updated forecast before making life choices.

There might be marital strife regarding the opening of the envelope.. or at least there was in our case.  I was chomping at the bit to open the envelope.  I wanted to wait, but I didn't.  We finally settled on opening the envelope the morning of the trip.  Teh German got pissed when I brought the envelope upstairs to potentially open it before we even went downstairs.  Siiiigh.  We ended up opening it right before we left, after I made the argument that I wanted to know where we were going so that way if we hadn't packed properly, we'd be able to grab stuff we needed.  Teh German struggles to argue with logic, so it was agreed.

Then I let Teh German open the envelope, poor life choice, because he took his time and I ripped his head off when he couldn't get the cardstock apart to see the destination page and I said, "JUST OPEN THE FOLDER ALREADY!"  Patience is not my strong suit, ok?  The envelope had been in our house for a week, to watch him stand there with the answer to the question we had been asked for an entire month right there and not just DO IT was physically painful for me.  I probably even grabbed at the stuff to do it myself.  I'm probably the worst.  Maybe.  Maybe not.  IDK.

Some of the contents of our folder:



Satisfied that I had packed everything for our location, we headed to the airport.  Once we got checked in and made it to our gate, we sorted through the folder.

We had:
-hotel reservation information
-tickets for a show
-a dinner reservation info sheet
-a few pages of facts about Chicago
-transportation info card
-3 pages of suggested things to do
-some other etc stuff

I knew that not all of our time would be planned, but I guess I expected more of our time to be planned.

From the suggested things to do, it didn't seem to be taken into account that it was a whopping ~35°F outside, which really eliminated a lot of "go check out this park" or "walk to ____".  Don't get me wrong, I said in the questionnaire that we liked the cold, but like, not to just be outside for extended periods of time without having an activity or purpose.  There's literally only so much cold a body can handle while the winds are whipping off the lake.

I also said that we were interested in breweries, cocktail bars, and eating.  Many places were suggested for us, but we cannot literally eat and drink all day.  We ended up doing breakfast most days, but not lunch, and then only kinda being hungry by dinner time.  If we stopped for drinks during the day, we ended up pushing dinner back because we weren't hungry.  It was weird and as people who thrive on a schedule, it was kinda difficult.  That's the downside about good food places, I want to eat all the things, and I cannot.  By the last day, we ended up sharing a meal because we were so full from eating other things.

I was disappointed that most of the suggested activities were food/beverage things.  I know that seems ironic since I had said we were interested in food/beverage, but we couldn't take advantage of most of the suggestions because we took a few of the suggestions and ended up being too full to take more of the suggestions.

Of the few non-food/beverage suggestions there were (music/comedy shows/museums/visit parks/boat tour), they provided tickets for a comedy show and we did the Chicago touristy things (Millennium Park/Navy Pier) and went to a suggested museum (which was an absolute blast) and did the boat tour (very interesting, although it was a bit chilly, which we tolerated without complaint until all the bridges kept dripping melting snow/ice on us as we passed under).  The only activities we did that weren't suggestions were the Gangsters and Ghosts tour (win) and going to the Maxwell Street Market (flop).

My goal had been to just go along with the suggested plans, but it was impossible because it was SO MUCH FOOD/BEVERAGE.  Truly.  Click on those photos and zoom in to read the sheets.  I spent at least an hour Saturday morning going through the provided suggestions and on my phone Googling things to do in Chicago that weren't food/beverage.  By Sunday afternoon, we had run out of things we really wanted to do.  We ended up spending hours at a brewery utilizing their free wifi and splitting a burger for dinner until it was time for us to head to the airport.  There were a few reasons for this.

We went to the planetarium and it didn't take nearly as long as we expected it to, so we had a lot more time to kill than we anticipated.  We didn't want to get to the airport too early since the beer options were better (and cheaper) by our hotel.  Additionally, we were tired.  It's exhausting packing as much as possible into 3 days.  Our schedule was wonky because our eating schedule was off and sleeping in beds that are not Teh Cloud is difficult.  I know that sounds "princess-y", but I'm just being honest.

So my overall opinion?

I would recommend Pack Up + Go to someone who wants a surprise, but personally, this was a once and done type of thing for me.  I had to plan more than I wanted to.  I wanted a few days worth of suggested agendas laid out.. but I guess I should caveat that with, reasonable agendas.  There's only so much food/beverage this human can consume.

We ended up spending a LOT on Lyft rides (~$160) because public transportation is overwhelming for me and Husband didn't want to figure it out either, I guess, because he never suggested taking the L for anything.  Our hotel was over a mile away from the touristy areas of downtown Chicago and I've watched enough Shameless to know that I'm not walking around Chicago in the dark.  Also, places like the Museum of Science and Industry and planetarium aren't close to the touristy areas NOR was it close to our hotel.

I did try to arrange our schedule so that things we did were kinda close to each other to minimize on Lyft costs, but by Sunday, we were having to debate on what to do in relation to having to pay for a Lyft to a destination/back vs not do anything and that's when I knew I was over it.  Having a rental car wouldn't have solved the problem because 1) traffic was horrible, 2) parking costs would have probably been about the same as the Lyft rides.

Was it worth it for the experience?
Yes.

Would I do it again?
No.

Total Money Spent:

Cost Activity
$1500 hotel, plane tickets, comedy show tickets
$160 Lyft
$50 Friday breakfast
$60 Architecture boat tour
$25 Afternoon brewery stop
$75 Friday dinner
$20 Pre-comedy show drinks
$15 Comedy show beverages
$40 Saturday brunch
$40 Museum of Science and Industry
$50 Lou Malnati's pizza
$60 Gangsters and Ghosts tour
$65 Breakfast in bed at the hotel
$32 Navy Pier Ferris Wheel
$45 Navy Pier time killing snacks/noms
$40 Planetarium tickets
$45 Afternoon brewery/dinner stop
$30 Airport beverages

$~2350

Total $$ Spent (+/-)


So yeah, it was A LOT of money for a weekend.  We had a good time though, so it was a worthy anniversary trip.  I can say that I would have never picked that hotel, so that was a pro and a con.  I am a Yelp Elite, so I am always using Yelp to determine our places to eat, I even do it in Charleston, so I probably would have ended up at a few of the places they suggested anyways.

I think the next time I want to go on a surprise trip, I'm going to trade planning services with a friend that knows us and our preferences.  I can still be surprised, the cost will be less, and they will know us personally to know that we can't eat all.day.long.


FYI: I was in no way compensated for this review, but I mean, if someone wanted to compensate me with free travels, I wouldn't say no.

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