I recently checked an extremely important item off my bucket list: I celebrated my birthday with a big, fat trolley party in Chicago and it was MAGICAL.
Firstly, if you have never heard of the concept of a trolley party I forgive you. But in all seriousness, in the case that haven’t, the concept is pretty straightforward: you rent a trolley for a certain block of time for you and a group of friends to make a series of stops (usually at local establishments, but you can really do whatever you want… you could even just have it stop at a bunch of different pizza places – they don’t judge) and the whole thing can be BYOB!
Whether you are local to Chicago or just visiting for the weekend, a trolley party is an excellent way to see the city and a unique way to celebrate a special occasion. Bachelorette party, birthday, you name it – this is a great idea. Trust me.
So, how to pull the thing off? Surprisingly there are a lot of moving parts to take into consideration, so I created this handy dandy 5-step guide for you (plus an amazeballs worksheet). There are a lot of trolley companies in Chicago, but for the purposes of this guide, we went with Second City Trolley. We had a great time and were very happy with our service!
Did you say worksheet?!
Sign up below to get this insanely easy to follow 2-page planning worksheet that will make you positively look like Mary Poppins and score you brownie points will all your friends. Were you put in charge of planning the bride’s bachelorette party or does your friend hate planning their birthday? This worksheet will make your life WAY more chill. And make you look super awesome.
Now go check your email! Got your worksheet handy? Okay, sweet. Now on to the good stuff. 5 easy steps to planning your trolley party:
Get a general head count & date.
Depending on the company you use, there are different sizes of trolleys for different capacities, usually starting with a minimum amount of 24 people (we used Second City Trolley and had a capacity of 25 people). Obviously, the closer you get to hitting the capacity, the most cost effective the trolley will be for everyone. Our trolley ended up at $30 a person (which included tip – we did ~20% of the total cost and split it up) and we had all 25 spots filled.
This is something to keep in mind when you are reserving the trolley – if some people are on the fence, it may be better to aim for the lower capacity so you don’t end up with a very expensive, partially empty trolley. Additionally, you’ll need to give the date to the company so it’s best to have one set prior to getting in touch.
Life Pro Tip: it may be a good idea to send out some initial correspondence (via email or text) to gather headcount and date information. This is also a good opportunity to take destination requests if you’d like your party to have some input or are having a tough time thinking of places. Check out the worksheet for a checklist of other info to include!
Create a loose itinerary (at least your pickup point).
When reserving the trolley, most places will want a loose itinerary – or at the very least, the address of where you are requesting to be picked up. Depending on where the company is located, some departure points can come with a fee. We were picked up at a residential address in downtown Chicago and had no fee.
Pick your trolley & reserve the date and time slot.
Decide which trolley company you will use. Some factors that can come into play here are cost, quality of amenities you are looking for (we had a no-frills, basic trolley, but there are trolley companies out there that have limo-like seating and other upgrades – depending on how fancy pants you want to get, this is something to keep in mind) and location of pickup. Again, we went with Second City Trolley based off a word of mouth referral and had a fabulous time.
It would also be a good idea to ask the trolley what their sound system set up is – if you need an aux cable to connect your phone or device to the speakers via the headphone jack (they usually have this, but sometimes it’s a good idea to bring your own – also, you’ll need to make sure your device has a headphone jack, or bring an adapter), if they will have garbage bags and ice buckets available, and how flexible they are with the itinerary if there are any last minute changes.
Finally, I recommend springing for the cleanup fee – unless you want to walk around with a garbage bag at the end of the night. The fee is totally worth it – especially if you are splitting up the cost amongst everyone!
Finalize itinerary and call ahead to any spots that might require a heads up.
This is where things get a little tricky. I started the planning process by making a list of my favorite nightlife spots – but there were about 87. In one neighborhood. Sooo seeing as we only had ours booked for three hours, I narrowed it down to 3 different checkpoints.
Like I said before, the driver will take you anywhere you want to go in a judgement-free zone (literally, you could take a Harry Potter-themed tour of Chicago and drink butterbeer all night), so it would be possible to hit more than 3, but trying to get everyone in and out of each destination is like herding a bunch of ADD zombie cats who like to party and you’ll need to factor in some additional time for each one. 3 spots gave us just enough time to unload, get a drink, use the restroom and get back on the trolley in a reasonable amount of time.
We also had everyone bring what they wanted with them to the initial pickup/meeting point, so we didn’t factor in any stops at the store. You could also have your initial pickup point be at a happy hour spot (like one of these!) or even start the day at the Lagunitas Brewery and then continue the party on the trolley. Up to you! If you’re not sure if a place will be able to accommodate your party on that specific day and time, it would be a good idea to call and give them a heads up. Also, I really wanted to make it to a karaoke spot, but it would have been near impossible to do as a stop in the middle of the evening – if you do want to hit up one, make sure it’s at the end!
Finally, you may also want to consider factoring in one spot for a picture op. The Adler Planetarium and Buckingham Fountain are crowd-pleasing favorites and the routes to get to them include gorgeous scenery!
As far as locations go, there are a few factors you’ll want to take into consideration:
- Proximity from pickup point.
- How long you want to be on the trolley to enjoy your BYOB bounty.
- Entry requirements (long line or password required? i.e. SafeHouse).
- Where you’d like your final destination to be.
We were being picked up near the loop, and we wanted a decent amount of time to get situated and crack open our beverages, so we chose to head to Emporium Arcade Bar in Logan Square first (about a 25 to 30-ish minute ride via side streets, which I had directed him to take to maximize our trolley time). We then hit up Fadó in River North (via Michigan Avenue, per my request, because it’s been a silly dream of mine for eternity) and finally ended the night at Kaiser Tiger in the West Loop.
These 3 choices were me to a T (I get really jazzed about being Irish and vintage video games, and Kaiser Tiger has bacon) so have some fun when you’re picking your spots!
Send out final details & info.
5 or so days before the event, you’ll want to send out final correspondence via email or text to confirm final numbers and other details. In this correspondence, you should include the following:
- Deadline to RSVP by.
- Initial pickup point/meeting place date, time and address.
- Instructions on what to bring – we let everyone know we would have a few things to share and cups, but that they should bring anything they wanted to drink with them. Note: most trolleys request that you stay away from glass bottles so you should communicate this to your guests.
- Food plans – we let them know we’d have some snackage but that they should plan to eat beforehand.
- Tentative range of cost per person based on the loose headcount & instructions on how to pay (i.e. Quickpay, Venmo & cash the day of).
Final Day-Of Information
You made it! On the day of your event or prior, you should plan to make a run for all the necessary items you’ll need. A few of the absolute basics are as follows:
- Cash for driver’s tip
- Device for playing music/aux cable
- Paper towels
- Spare trash bag
- Container for ice
It would also be a good idea to designate one person to take care of the music during the event and one person to take care of final payment and tipping to the driver. That way everything is smooth sailing and you can enjoy your event instead of worrying about the details. Finally, it also might be a good idea to start a group text message or chat with everyone on the trolley so you can easily communicate when it’s time to head out.
Don’t forget about this printable worksheet for easy party planning! Plus, you’ll also get list of some my favorite good-for-groups destinations for your next trolley party. Sign up below: