Along with the two Cubs games we attended, my mom and I packed a lot into our short trip. She had given me a list of things that would be cool to do/see while in Chicago and we accomplished a good number of them. We loaded money on our Ventra cards, which is the key to getting around with public transportation that we were always using. You can get a new Ventra card or load money on an old one, at any of the train stations. My advice is to take the trains, they are very easy to follow and they also come pretty often. Using the Google Maps app is a must, since it will give you pretty accurate estimates of bus arrivals and there are a ton of buses in the city, so they can easily be used too. Just be careful riding the trains at night or alone; there are some strange characters out sometimes. My friends who live there prefer to Uber, but since my mom and I never get the chance to take trains that was our preferred travel method.

The first activity on her list was to ride bikes around Lake Michigan. This was my forte. Every single summer I have rented Divvy bikes to bike along the lake. Divvy bike stations are all over the city – I’m talking every couple of blocks. It’s nice because you rent them from one station and you can return them to a different one. They have a place to put your bag on the front and they’re easy to ride bikes, but a little bulky. You can sign up to use a bike for 24 hours, but the only part that is annoying is that you have to check the bike into a station every 30 minutes or sooner. If you don’t get to a station within the time frame it will start charging your card extra money. Having stations all over the city makes it doable, but when you want to take your time and maybe stop to take some pictures or put your feet in the lake you are on a time crunch. Thankfully there is a Divvy app that shows you the closest bike stations and how many bikes are available or how many empty docks there are. I’m on the app religiously when I am renting the bikes because I am not trying to get charged extra. I think it would make a world of a difference if they allowed you an hour without having to check in the bike.

My first summer here I went bike riding with my friend Sarah until she was getting annoyed at me for making her bike so far. Another summer I went bike riding with my boyfriend and after a few miles, he asked me if we could go back and take a nap, which was disappointing. I knew my mom was up for the challenge so we rented bikes at the Granville Station, up north, since that’s where my friends’ apartment is, and biked all the way down to Millennium Park. We biked Lakefront Trail and it was super easy to find since it’s the trail right on the lake. We biked about 9 miles, having to check our bikes in probably about 5 or 6 times during our ride. I took her past Oak Street Beach, which gives the best view of the city (I think) and we checked in our bikes at Lincoln Park Zoo to walk around the animal exhibits and grab some ice cream. This zoo is awesome because it’s free, open every day of the year, and has a good number of animals. I wanted to bike through Grant Park, but Lollapalooza was happening the week we were there so the park was all fenced off. While my mom was behind me the whole ride, I am extremely proud of her. Not even my boyfriend and friends want to do that whole bike ride and it was a hot and humid day.

We stopped at the iconic Cloud Gate (aka The Bean) briefly. The park was extremely crowded. Then we decided to check out Chicago’s Pedway, which is like a maze of tunnels, underground and above ground, that connects buildings to others through walkways with little shops. It is really practical when it is raining or freezing out since if you navigated it right you wouldn’t have to walk outside. We were attempting to walk through the tunnels, but after our first turn, we were lost so we decided to grab a light lunch above ground. We had tea and sliders at this tea chain called Argo Tea Cafe. It’s like a Starbucks, but all tea. We really enjoyed it. To finish off our busy day we went to the Cubs game.

Second on the list was kayaking on the Chicago River. We took the train as close as we could then we walked to Wateriders. It was $20 per hour for each person, whether you get a single kayak or a double kayak and $5 for every 15 minutes after. I liked that they charge by the quarter hour instead of the whole hour. We didn’t make any reservations, but we had no issues getting a kayak right away. My mom and I decided to go with a double kayak that way if one us got tired of paddling the other could make sure we didn’t start floating in the wrong direction. They gave us a brief safety presentation and we were off.

Thankfully it was an overcast day so we weren’t too hot because we definitely didn’t want to go swimming in the dirty river. We made sure we stayed on the correct side to avoid getting hit by the larger boats and we had a great time. The day before we were working our legs out on the bikes, now we were working our upper body by the constant paddling. I wanted to take some breaks for a couple minutes along the way, but my mom kept paddling behind me the whole time. She’s amazing. It was cool going under the bridges while the cars drove over you and to be surrounded by the beautiful skyscrapers of downtown. While I love nature, Chicago’s urban jungle is a stunning sight to behold. It was definitely a different kayaking experiencing for us. We went East towards the last bridge before Lake Michigan and then we turned around and headed back to where we rented the kayaks. We were out there for a little under 75 minutes, but they only charged us for an hour each so that was nice. We got back just in time too because it had started sprinkling and they weren’t allowing any more kayaks to go out in case it stormed. We lucked out.

We grabbed lunch at Ironside Bar and Galley downtown to sit and watch the Cubs game, but it was delayed due to rain. Thankfully we didn’t see any of that rain while we were downtown. The lobster bisque at this restaurant is so full of lobster chunks. Usually, places aren’t generous with lobster meat, but this place was the opposite. Also, the lobster tater tots were so delicious!

Next on the list was the Skydeck at Willis (Sears) Tower – the tallest building in America. I had never been up there even though I had been to Chicago three times before. It is kind of pricey at $23 per person, but it’s not just a view. You can read about the history of Chicago and interesting facts about the city on the lower level. There’s a short video you can watch, which shows you how Willis Tower came to be and even the elevator ride to the sky deck is fun and fact-filled. The Skydeck is full of windows and has a souvenir shop. On the West side of the tower they have thick glass that juts over the edge of the building, so you can stand on it and look directly 103 floors down upon streets and buildings. I’m not scared of heights, but when I walked out onto it, it made me feel a little anxious. There’s a short line to stand in to get on the glass floor. Since you paid $23 I’d recommend waiting and making sure you get some good photos. We went in the evening, so the sun was setting on the same side so there was some glare on the big glass box. Your best bet for the best views and pictures would be to go earlier in the afternoon or even morning so you won’t get those glares. Looking out over the East side we could see Lollapalooza going on at Grant Park. There was such a massive group of people at the main stage that it didn’t even look fun, but maybe that’s what EDC would look like from 103 floors up to.

Thursday night it was one of my friends’ birthdays so of course, we went out to celebrate. She loves Mexican food so we took her to Tuco and Blondie. This place had good food and even better drinks. The black cherry margarita was to die for! Then we went to Parlor Pizza Bar at Wicker Park for a few rounds of drinks, since my friend works at one of their locations and gets half off, and continued the night bar hopping down the street. While at Parlor I couldn’t help but look at their food menu (I love food!!) and, oh wow, they had some delicious looking pizzas. If we hadn’t just eaten I definitely would have ordered one. We went to a couple more bars briefly until we were quickly kicked out of one a little before 2 am. I forget that places outside of Vegas close so early. It was a great night with my friends and I’m thankful I was there to celebrate another birthday. Happy Birthday, Lucy!!