When I booked my flight to Chicago, I had no idea what I was going to do there. Even 2 days before going to Chicago – I had no idea what to do! I did a quick search on Tripadvisor, my all time favourite online travel advisor and the number #1 thing to do was Bobby’s Bike Hikes. Knowing that I would probably be doing a lot of eating in Chicago, I knew I needed to do something that required a great deal of exercise so the bike tour seemed like a good idea.
On the website was a 3 hour Lakefront Neighbourhood Tour which is the tour that made Bobby’s Bike Hikes famous. They promised to take you to quiet neighborhood streets, city parks, and packed beaches of the North Side of Chicago. The highlights of the tour are Gold Coast Mansions, Oprah’s House, the Playboy Mansion, Lincoln Park Zoo, Old Town Historic District, North Avenue Beach, and the Lakefront. I love cycling and haven’t done it in a long time so I signed up right away!
The morning after I arrived I woke up early, had my breakfast and walked over to the River East Docks which was only about a 10 minute walk from my hotel. The tour started at 9:30am and it was already a bright and sunny day!
Sammylicious TV: Bobby’s Bike Hike Tour Video
If you watch the clip above, you can see how we ride along the beach to this even more amazing spot where you can view the Chicago skyline in full view. So awesome!
I was a bit over ambitious and wanted to record a video with one hand and steer my bike with another. You’ll see how I end up riding through a puddle of dirt which I get completely splattered with. Lucky I cut the video just before that!
Bobby’s Bike Hike Tour Photos
I don’t recall my tour guide’s name but he was extremely enthusiastic and knowledgeable about the city of Chicago and all its neighbourhoods. He was also very mindful of all the riders in the pack and made sure everyone was safe and having a good time.
There were riders from all over the USA and of all different ages and fitness levels. It was really good that the tour wasn’t too difficult and was a comfortably easy ride that it was very enjoyable. It was so good to ride with the sun beaming on your face and arms and the wind in your hair.
Our first stop was the Museum of Contemporary Art which is also not far from where Oprah’s house is. I forgot to take a photo – sorry!
We then rode up to the Gold Coast, where many millionaire homes reside – thus why this neighbourhood is named the Gold Coast!
We rode up to Lincoln Park where there’s a lovely monument of Abraham Lincoln. It is said that this park used to be a graveyard and is thus now haunted. No one has been able to prove such a theory but no one has yet to prove the theory wrong either…..
We then stopped off at Old Town. Old Town is a beautiful little town with cute little bungalows. It’s a very quiet neighbourhood in Chicago.
See these cute houses in Old Town!
We paused for a break in Old Town by a church.
This church is the only surviving building from the Great Chicago Fire in 1871 which killed thousands of people and burnt down many buildings. While most of the char has been cleaned from the building, there are still some that remain in memory of the event.
Inside is a beautiful church.
This was one of my favourite parts of the tour – we got to visit Lincoln Park Zoo! Lincoln Park Zoo is not far from Lincoln Park and has free admission! Now just because it has free admission, doesn’t mean it’s a lousy zoo. It had some pretty awesome animals to check out. I didn’t have enough time to see the whole zoo but I still got to see plenty!
Deer!
Zebra!
Sichuan Takin
Alpaca!
Kangaroos!
Then, I bumped into a squirrel wondering around
From all the way at Lincoln Park Zoo – you get a pretty awesome view of the Chicago skyline!
Here’s me with my bike and Chicago!
After all of that, we were off to the beach. Look how amazing the sun was at this hour! Believe it was just 11am.
What a lovely peaceful beach. I love that you can ride along here. The path takes you all the way back downtown. Very cool!
Here’s the panorama I took from the spot. Chicago looks so nice. From here, we rode all along the water back to that black building situated on the very left. It looks far but it didn’t seem that far because it was such a lovely ride. There were a lot of people jogging and biking along the water as well.
Arrival back downtown! Here’s Chicago wasting water by spraying the harbour. Pretty though! Haha.
In all, I highly recommend Bobby’s Bike Hikes. I recommend all bike tours but in particular Bobby’s Bike Hikes! I recommend renting bikes! I recommend biking anywhere! I just love bikes now.. and I love Chicago!








































