Playing Tourist in Chicago This Summer

Chicago River bridge

I often joke that I only put up with Chicago winters in order to get to Chicago summers. Street festivals, rooftop bars, beer gardens and running along the lake front have been some of my favorite ways to spend summer weekends over the years.

This summer seemed to fly by – likely because the temperatures felt like spring through most of June and then I spent most of July over in Europe. So once August rolled around, I wanted to make the most of what summer remained and Viator stepped in just the right time.

Viator is a tour booking site with offerings all over the world. I started working with them during my career break trip, both to take some of their tours to review them, but also to write regularly for their “Things to Do” blog about both Russia and Chicago. When they approached me to work with them on an Instagram campaign to highlight must-do summer activities for locals in Chicago, I couldn’t resist (check out the hashtag #ViatorMyCity on Instagram). So over the course of two weekends, I checked out three different Chicago tours (all of my choosing), experiencing new parts of the city and learning a lot more about the placeI have called home for nearly 15 years.

Chicago activity list

First up was a Southside Neighborhoods Bicycle Tour on a sunny Saturday morning. The tour covered about 14 miles overall, with frequent stops along the way all focusing on Chicago’s infamous gangster past and the historical conflict between north side and south side gangs. We actually spent the first hour on the north side, stopping outside of the Holy Name Cathedral and again near Trump Tower overlooking the Chicago River. Then we headed down to the newly opened river walk and biked over to the lakefront path to Museum Campus. From Museum Campus, we made our way to Chinatown and Pim Tong Park, which sits right on the river. I had always wondered where the park was, as it is a stopping point for water taxis, so I was excited to finally stop there!

Pim Tong Park

Bike selfie

After Chinatown, we took a quick spin through Bridgeport to check out some old gangster haunts. We unfortunately weren’t able to stop for pictures because apparently some of the residents don’t appreciate the tours coming through, but I was impressed by the very cute neighborhood not far from US Cellular Field. Finally, we headed over to the 31st Street Beach, which offered great views of the skyline to the north, and then took the lakefront path all the way north again to the bike shop where we started. Overall, it was a great work out and a great way to see more of Chicago. It also gave me a chance to get a feel for biking in the city – something I haven’t done at all in 15 years!

31st Street Beach

The next weekend, I got to explore the Chicago River in a new way – by kayak! I’ll admit I was slightly terrified as I slid into my single kayak to start the Chicago River Kayak Tour. I hadn’t been in a kayak in more than a decade and I really wasn’t sure whether I’d be able to do it. Luckily, the three guides that joined our group of 20 or so were great and my fellow kayakers were understanding when I accidentally bumped into them because I couldn’t stop. The tour itself didn’t cover much of the river – we just went down the north branch to Wolf Point and then across to the main stem as far as Trump Tower. But we stopped several times to hear stories about the history of Chicago and the river.

Wolf Point view

Kayak tour guide

We also made a somewhat ill-timed stop along the river walk to photo bomb a wedding party. They took it in stride, though, eventually asking us to pose behind them with our paddles in the air as the photographer snapped away.

wedding party

By the time we returned to the kayak shop in the old Montgomery Ward’s building along the north branch of the river, my arms felt ready to fall off, but I had learned even more about my adopted hometown and I was confident enough in my kayaking skills to think about doing it again!

Willis Tower view

The next morning, my arms still sore, I headed to Water Tower Place to join the last of my three tours – the Chicago Crime and Mob Tour. This was just an hour and a half long bus tour (which proved to be a good thing as it looked like it could rain at any minute throughout the tour!) but it covered a lot. We cruised up Lake Shore Drive first to Lincoln Park, listening to stories of bank robber John Dillinger along the way. In Lincoln Park, we would stop at the old Biograph Theater to hear the story of how Dillinger was shot and killed by FBI agents in a nearby alley.

From there, we cruised through River North past the Rock’n’Roll McDonald’s, where apparently cashiers once sold crack out of the drive through window. We passed the site of the old jail and courthouse on our way to Harry Caray’s restaurant – a place I’ve been a number of times, but never knew a gangster named Frank Nitti once lived upstairs or that there were apparently tunnels underneath the restaurant connecting to other buildings in the neighborhood. In the basement of the restaurant, we got to visit “Frank Nitti’s Vault,” named for the vault that was found in Nitti’s upstairs apartment.

Harry Carays

Frank Nitti vault

Our last stop, of course, was the Holy Name Cathedral that I had already visited on my bike tour the previous weekend. It was fascinating to hear how two different tour guides approached the stops there, with one insisting that a small hole in the facade was a bullet hole from a gangster shootout and the other convincingly telling us that is all a myth.

Holy Name Cathedral

Bullet hole or not, I will never look at Holy Name Cathedral quite the same again (and to be honest, I had never really thought about it much before. And that was one of the great things about the three tours I took this summer with Viator and the ones I took in the past – no matter how long I have lived in Chicago or how well I think I know the city, there is always more to learn and more to do for the first time. Just because you’ve lived somewhere for a long time doesn’t mean you can’t take a step back to explore it with a tourist’s eyes every once in a while.

(Disclaimer: Viator and/or the local tour operators provided me with complimentary admission to the Chicago tours mentioned above and I was compensated for the Instagram campaign, but all opinions are my own).

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3 thoughts on “Playing Tourist in Chicago This Summer”

  1. Loved your post! This is first time I am visiting your website and I find your posts very very resourceful..
    Keep up the good work…I will love to visit your site from time to time…..
    By the way we have shared this post on Twitter

  2. Wow.. Chicago is my favorite spot.. really i enjoyed to reading this article and i am enjoyed to see these various locations.. really in my future plan i will cover those places

  3. I am determined to play tourist in Chicago this winter, starting with a tour of the Pullman District this Sunday. What a great city we live in, but it’s so easy to get caught up in day to day life!

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