Chicago fun: a review of Bobby’s Bike Tour.

One of the things I love to do on vacation is cruise around the city on a bike. It’s so fun.

Recently, I’ve done bike tours in Portland and New Orleans. Now I can add Chicago to that list. 🙂


My friend Ginger and I meet up once a year in a different city. This year, it was Chicago. We packed a lot into our three days! We ate, walked, shopped, biked, boated, and also just relaxed.

I was really looking forward to the bike tour, because I’ve had such great experiences in other cities…but I have to say that this one was a little disappointing.

We chose Bobby’s Bike Hike, because they got stellar reviews. While our guide was fantastic, there were several things about the tour that weren’t. Here’s the scoop:


Bobby’s Bike Hike was a little hard to find, so allow for a few extra minutes.


It’s kind of tucked into the center of a building, and you have to walk down an alley to get there.


Getting started.

Once we found it, the scene was a little chaotic. There were a couple of tours coming and going, people were milling around and yelling instructions, and it wasn’t really clear what we were supposed to do.


We eventually figured it out. We were supposed to sit in the office and wait as our tour assembled. This took longer than you would think. Everyone had to sign in and sign a waiver, fit themselves for a helmet, listen to instructions, and possibly buy water and use the restroom. Since there were about 20 people on our tour, you can do the math. 😉

After everyone was ready, we had to line up by height and file out of the office and back into the courtyard, where we got bikes. We couldn’t just go and get a bike – they had to give one to us. This took a long time as well.

At this point, we learned that there was a woman on our tour who didn’t know how to ride a bike. Her friends thought it would be “funny” to book the tour and see what happened. Luckily, one friend agreed to ride on a tandem bike with the non-biker, but I was surprised that Bobby’s Bikes let her ride.

The tour itself.

We biked for a total of about 6 miles, over a period of about 2 hours. Since it was such a large group, we biked very slowly and stopped often.

IMG_2366According to the website:

This tour is what made Bobby famous, taking you off the tourist beat and onto the quiet neighborhood streets, city parks, and packed beaches of the North Side of Chicago, giving you a glimpse as to how Chicagoans enjoy their beautiful city. Highlights include the Gold Coast Mansions, Oprah’s House, the Playboy Mansion, Lincoln Park Zoo, Old Town Historic District, North Avenue Beach, and the amazing Chicago Lakefront.

IMG_2372While all of this is true, the tour feels very “processed.” We felt like they were just checking these items off their list. I think the size of the group (20 or so) had a lot to do with this. With a smaller tour, I guess it’s possible to tailor it a little more to what the group wants to do.


The former Playboy Mansion

The spots we hit on the tour were interesting, but I feel like I didn’t really connect with any of them. Again, I think this is because we just stopped for a few minutes at a time and took pictures.

IMG_2368Would I do this again?

I might give this another try, but if I did, I would book a more specific tour. We booked the “Lakefront Neighborhoods” tour, but I would probably opt for the “Bites, Bikes and Brews” tour next time. I imagine that it would have a more personal feel and more of a point of view.

Have you done a bike tour before? Did you like it? Would you do this one?


  1. Have not done a bike tour but did a Segway tour in Washington D.C. which was a blast.

    But I am curious how they would mix “brews” into a bike tour. :{

    • Points Pixie says

      Anne – Segways sound fun!

      In terms of the brews – I hope the tour would stay on the quiet back streets?

  2. Have never done a bike tour. Running, I find is another great way to see a city, learn about a neighborhood. Bike tour sorta sounds interesting, if a smaller group. This one feels like it screams TOURIST. Cute pics, why does Ginger’s have a number? For a moment thought it might be a race 🙂


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