Hey there, Katie again. Back in July 2019 Tony and I signed up for a Gangster and Blues walking tour in Chicago. So more detail on my date planning. When I made the decision I wanted our dates to be more interesting and less generic, I needed ideas. Pinterest became my best friend and still is for date planning. I simply searched for “date ideas”. Out popped lists of dates. My favorite pins to research into were labeled A-Z dates. Basically, each letter of the alphabet has 2-3 correlated ideas. W for a walking tour. I take the idea and then research the idea with Chicagoland.

When I researched walking tours in my area there were numerous options. The benefit of living in a metropolitan area. Next was to actually decide on a tour. First I choose a tour company. I found one that seemed like an interesting concept. Free tours by foot. Basically, you reserve a time and you pay at the end of the tour what you believe is fair. I have come to hate this concept, lol, for the fact I judge myself. What if it wasn’t enough, what if they think I’m cheap? What if it’s too much, now I just wasted money? What if everyone else paid this much and I’m way off? Yeah, I personally prefer a set price.

Nevertheless, I went with that company. So next was choosing which kind of tour. They had about 4-5 different types of Chicago walking tours: Millennium Park, River Walk, The Westloop, Ghost Tour (always have to throw in a ghost tour option), Lincoln Park Gangster Tour. We choose the former. 

Day of the date. We leave and our drive is going well until we get into Lincoln Park. What originally was 5 minutes to arrive at our parking spot (I used spot hero), ended up talking 20 minutes! My 15 minute buffer time was taken away. We start to panic that we won’t make it to the meeting spot and even if we didn’t lose any money, we would have wasted over 2 hours driving. To top it off…I really needed to pee. We park and thank god the meeting spot was right outside the parking garage. As soon as we walked up to the tour it was ready to start. Literally the first words out of the guide’s mouth “Hope no one needs a restroom because there is nowhere to stop on this 1.5-hour tour”. NOOOO!!!! 

It was a beautiful day out, the tour was interesting. Overall Tony and I had a great time. I was able to keep my mind distracted enough I could forget I needed a restroom. Thankfully the tour ended at Lincoln Park Zoo, meaning available public restrooms. After the tour ends the group splits and you’re on your own to make your way back. So we took a nice walk back to the car discussing the things we learned on the tour. Overall I really liked this date. We will definitely try out another walking tour at a later date.

Hey guys! Tony here chiming in on this one..,

For me, this was a really fun one. While a lot of the buildings have been torn down and rebuilt we did see where the St. Valentine’s Day Massacre happened. As well as seeing where John Dillinger died. There were some great north side blues joints too. Overall any day in the sun walking around is a win, add in gangsters and history even better… all I needed was some festival food to walk around with lol. Though!! We did have the most annoying woman in our group, she was constantly trying to add to the tour and correct the guide. There is always one isn’t there lol.

Here is the link for the walking tour we took. If you are in the Chicago area it is totally worth it!

https://freetoursbyfoot.com/chicago-tours/walking-tours/lincoln-park-blues-tour/

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