This page includes affiliate links. If you choose to buy through these links I may earn a small commission with no additional cost to you!
While Chicago is know for its windy and wild winters, its summers more than make up for the frosty seasons.
I took my first trip to Chicago in August, and the warm weather had me sticking close to the Chicago River for the entire day.
My first stop was Navy Pier. Half fairground and half public space, the waterfront promenade features a merry go round, a Ferris wheel, several museums, and enough food, drink, and seating to make the area an entertaining way to spend day out.
I made note of a summer schedule of events, including a weekly fireworks show and free yoga sessions. Unfortunately I wasn’t around for any of the scheduled events, but it was nice to know that there was community engagement.
I briefly debated taking a last minute tall ship cruise around the lake but nixed it in favor of beginning a lazy rooftop bar crawl.
Offshore Rooftop Bar is located right at the end of the pier, so it was a convenient way to begin my trip. Plus- I’d walked here from the metro, so I was just about ready to sit down. I was originally a little confused by the entrance to the bar- I’d tried to take the stairs, but they didn’t seem to go up to the rooftop. Instead, I was compelled to take the elevator- at least it’s wheelchair friendly.
While I imagine that reservations to this bar fill up quickly, I was able to get away with a drink at the bar right away since I was on my own. Offshore has two sections- one is an enclosed glass area, and the remainder of the rooftop is taken up by comfortable looking outdoor seating with a great view of the surrounding shoreline. Despite the air conditioning doing its best, the summer heat had me feeling like I was in a greenhouse, but the bartenders were as quick with the ice water as they were with tourist recommendations.
When I finished my drink, I headed back down the pier, picked up a snack from one of the many vendors, and began making my way down Chicago’s famous Riverwalk. The multi-use area is located low along the Chicago River, out of the way of the busy nearby roads. There are a few bars and restaurants along the walk, with playgrounds for kids and bike lanes for those looking to move a little quicker. I loved seeing the skyscrapers loom over the river from this perspective. I made note of a sports shop that was renting out kayaks and have jumped that to the top of my to-do list on my next visit to the city.
As it was, I was already getting overwhelmed by the heat and decided to make my way to the LH Rooftop Bar for another drink. Again, I was lucky enough to zip right on up to the small rooftop on my own, while larger groups were redirected to the interior bar to wait. While I feel like LH Rooftop has a more iconic view of the Chicago River, it was definitely a much smaller space and more crowded than the previous rooftop- especially with more than half of the area blocked off for “VIP Guests”.
Although there was a pitcher full of ice water available to the public, there was also no coverage from the blazing sun and I quickly found myself sliding into heat exhaustion. I ended up having to quickly finish my drink and head down a level to to the covered and air conditioned bar below. The bartender was very patient with me chugging down about six glasses of ice water in quick succession and even helped me decide which of Chicago’s famous viewpoints to check out.
Through the power of asking literally everyone I came across, I eventually decided to book a ticket to the 360 Chicago Observation Deck rather than the Skydeck. Willis Tower is such an iconic building in Chicago, and I wanted to be able to see it from the tower I chose. Unfortunately, almost immediately after I booked this non-refundable ticket, I was informed that the Hancock Building (where 360 Chicago is located) has a Signature Lounge one floor up from the observation deck. While the cocktails are almost the same price as a ticket to 360 Chicago, you get nearly the same view and you can always “change your mind” and head out before buying a drink (but don’t tell them I told you!). Moral of the story- Ferris Bueller is always right and I should have gone to the Willis Tower.
As I was already committed to 360 Chicago, I did end up having an excellent time. Since the tickets are based on a timed entry, it’s a quick line to the elevator. The staff takes a picture of you with a fake background to purchase later and then you get rocketed up 94 floors at 20mph.
When the elevator arrives about 60 seconds later, you’re immediately faced with the gift shop, a bar, and enormous floor-to-ceiling windows, some of which allow you to tilt out over the airspace below for an extra fee and a dose of vertigo. The side opposite the elevators has a nice seating area to relax and look out over the city. One of the things that I really liked about this view is that it was so close to the lake that it had uninterrupted views of the shoreline as well as the city behind it. It really emphasized the dichotomy of the sunny sandy beaches, and the concrete and steal skyscrapers right on top of one another.
As my last stop on my admittedly packed day, I hopped on an Architecture Boat Tour. Let me tell you- this was the number one thing that was recommended to me by literally everyone I came across. The bartender at Offshore? “Definitely make sure to do an architecture cruise”. The couple I met at LH Rooftop? Rave reviews about their architecture tour. My friend from Chicago? “I’ve been on this cruise three times”.
It was a little expensive, but with such praise how could I resist? The tour took about an hour and half and the live commentary from our onboard guide finally put into perspective the buildings that I’d been running around all day. Chicago has some really unique skyscrapers (St. Regis is my personal favorite), and this cruise took me much further than I’d walked on my own, pointing out even more interesting buildings and the historical context behind them. The cruise ended with a fantastic view of the Chicago Skyline from Lake Michigan, though since we were on a sunset cruise, I was mostly blinded by the sun for this bit. Overall, I’m now an architecture cruise believer- make time for this on your own visit!
With so much to do and see along the river, I think I have developed a really romanticized, summery, idea of what Chicago is like as a city- but summer adventures like these are exactly what makes visiting Chicago in the Spring and Summer such a good idea. I spent an entire day in and around this very specific part of the city and still managed to leave with more things to do than when I arrived!