Chicago in 24 hours

Yesterday Captain Seahorse and I got up super early and hit the road to Chicago. This was my first trip to Chicago, so I was a little excited. Along the way, we saw a few surprises like windmills for miles and Fair Oaks farm.

Bike Tour
Since I had never been to Chicago and we were on a time crunch, I had to maximize my time here and fill it with activities that allowed me to see as much of the city as possible. Our first activity was a bike tour with Bike and Roll-Chicago. We have found when visiting new cities, tours are a fun way to help us take in the sites and get a little knowledge of the layout of the city.
The bike and roll tours start in various places in the city depending on which your you decide to take. We thought the tour started at Millenium Park, which allowed us to check out the famous “bean” on the way to pick up our bikes. When we arrived at the bike place we were actually informed we were to start at Navy Pier. They allowed us to go ahead and get our bikes and gave us a map to get us to Navy Pier. 

Fortunately this ride was all downhill. We did however get a little confused on directions in this 10 minute ride. No one told us how to cross the river, but we figured out. We had to loop round and cross a bridge. Once we did this, getting to the Navy Pier was easy, finding the start of the tour was not. We sat at the entrance of the Navy Pier for about 3 or 4 minutes and had to call to find out where they were located. As we were pulling up to the kiosk, a group of people were leaving on bikes. Yup, you guessed it! Our tour was leaving. 

After talking to the girl, she called our tour guide, Matt, to see if he could come and get us or meet us. In the mean time I was looking at the tour route on a map and decided I knew where to go. So, we left. I was quite determined to catch up to the group so we wouldn’t miss much. Now, although I knew the direction of the route, I didn’t know the stops. So of course we rode right by the first stop, and wouldn’t you know that’s where they were. Luckily, the lady from Bike and Roll got in contact with Matt and he was looking for us.

The tour was a lot of fun. We saw various landmarks throughout the north side of Chicago, such as “Bunny Beach”, John Hancock Building, Lincoln Park and zoo, and one of the only wooden alleys left in the city after the Chicago Fire. 

We had an overcast for the majority of the day. It did rain a little while biking, but Matt was prepared. He had ponchos for everyone. We had to follow Matt back to Millenium Park to return our bikes after we dropped everyone off at Navy Pier. He took us through the bottom of a bunch of buildings to catch an elevator so we wouldn’t ride up hill-a little scary but very cool actually. 


After the tour it was lunch time. We asked Matt and the other lady at Bike and Roll for pizza suggestions because what is a trip to Chicago without pizza. They both said Giordano’s or Lou Malnati’s-apparently they taste a lot a like because two brothers ran one pizza place, one got mad at the other, left and started his own. 

So after a quick potty trip, we went looking for Giordano’s. It was only about a block and a half away. 

Giordano’s is a Chicago institute known for its deep dish stuffed pizzas. We had the small meat and more meat, a deep dish stuffed pizza with pepperoni, sausage, salami and there was one more but I don’t remember what it was. It was soooooo good! I did have a drink, but I don’t remember what it was called. It was just ok.

Giordano's Pizza on Urbanspoon

After Giodano’s, we did a little shopping, or looking actually. We had every intent to do some shopping on Michigan Avenue, also known as “the Magnificent Mile”, we checked out State Street on the south side of the river and ran out of time. State Street has Macy’s and Sears as well as a few other trendy stores, while Michigan Avenue is more high end with Coach, Tiffany & Company and other luxury shops and boutiques.

We checked into the Springhill Suites on Deerborn to give our feet a little rest. I could also tell Captain Seahorse was getting a little sleepy, so I hoped he would take a nap. He didn’t take a nap, we opened a window and listened to the sounds of Chicago and rain. 

As a surprise for Captain Seahorse, I bought tickets to the White Sox game against the Baltimore Orioles. So after our rest we got directions to US Cellular Field for the game and started on our journey. We walked about 4 blocks and caught the “L”, I’m assuming that’s how they spell it. 

It was quite the ride. It wasn’t as busy as I expected with it being about 545 on a weekday but our train was still kind of full. We did however see a little illegal activity, which was kind of mind blowing at the moment. Then we missed our stop, so we got off at the next stop and caught the next train back.

We were a little late to the game but not much. Neither of us are baseball fans, so we watched a little of the game but did more eating and people watching than anything. We both got kind of bored and left in the middle of the 7th inning. We found out later the “O’s” won.

Boys’ Town

After getting back to the hotel, catching our 2nd wind and showering we headed to Boys’ Town. Boys’ Town is ironically the gayborhood, gay neighborhood, of Chicago in Chicago’s Lake View area on the north side. The “L” put us right across the street from Wrigley Field and we walked a few blocks to find the rainbow flags hanging everywhere.

Boys’ Town was a lot of fun. We walked about 3 or 4 blocks hitting at least the top 3 clubs-Hydrate, Progress, and Roscoe’s. Hydrate, according to one of the sites I used while researching the area, is probably the most popular club on the strip. It has 2 bars and is home to Dida Ritz from Ru Paul’s Drag Race. The club was quite dead but had a great drag revue. Captain Seahorse was very happy to Dida Ritz in person. 

Roscoe’s is another top club in the area. When I did my research, it said it was kind of the spot to start the night off before hitting the other clubs in the area. With 3 bars, an outside patio and a dance floor, this place was crowded boots. It didn’t look like it would be dying down either. 

Progress is directly across the street from Roscoe’s. I am assuming this is a newer venue to the community because I didn’t find it during my research but it was a suggestion and seemed to be pretty packed when we arrived. The DJ was pretty cool. We stood and watched him for a while, seemed to be in his own little world and had the crowd going. Progress also has some of the coolest light fixtures I’ve seen. They are made from light bulbs. 

We headed back to the hotel to get some sleep for the night. We drove back to Indiana this morning for the family cookout. We packed a lot of things into 24 hours in Chicago and had a blast doing it.

One response to “Chicago in 24 hours

  1. Wow – you definitely packed a lot of Chicago into a very small time frame! But, as a Chi-town native I have to tell you, it's Hancock not “Handcock”… Don't even get me started on Willis/Sears!


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