For a first time visitor to USA Chicago, you may consider to purchase a tourist pass to visit some of the common attractions. I was choosing between the Chicago CityPASS and the Explorer Pass by Go City.

I purchased the Go City Explorer 5-choice Pass for $118.75 after 5% discount off $125 (Use discount code ‘DESTINATION’). I think you can get 10% off if you use my referral link.

The 5 attractions I chose, in order of priority, were:

  1. Shoreline Architecture River Tour
  2. 360 Chicago
  3. Field Museum
  4. Adler Planetarium
  5. Hop-on-hop-off Bus

I had originally wanted to purchase the 3 or 4-choice pass as I was mainly interested in #1-#3, and #4 was nice to have due to a Mars Occultation event during my stay. I bought the 5-choice pass because the price difference was small after discount. After going through the experiences, I would say #1-#4 were worth the trip, but you should skip the hop-on-hop-off bus in Chicago.

Shoreline Architecture River Tour

The Architecture River Tour was recommended by a friend who studied near the area, because Chicago is supposedly the birthplace of highrise skyscrapers. The cruise on Chicago River was a nice way to look at the city and the architectures over different periods. For example, the buildings built after the Great Depression in the 1930s were modular and boxy, the most no-frills way to get the economy started again, and things start to get more modern and fancy as the economy become more prosperous. The guide also spoke about the architecture tricks used to stabilize the buildings in the Windy City, so that you don’t feel seasick in your high-rise apartment.

For a first-time visitor, I recommend the River Tour too. The guide would usually give some recommendations of nice things to do or eat in Chicago. No prior booking is required under the Go City pass. However, on the day of my visit, I went to the station at Navy Pier to realize that it was not opened that day, so I had to take a bus to the Michigan Avenue station. Tipping is encouraged so do prepare some cash.

The cruise for Architecture Tour on Chicago River. The prominent building in front is Trump Tower.

360 Chicago

I was choosing between 360 Chicago and Chicago Skydeck, but I chose the former because of the “TILT” and that it was near my hotel. I chose a slot at 9pm because I wanted to avoid the crowd and I think the night view is nicer.

The Go City Pass only covers the entry to 360 Chicago and does not cover the TILT ride, but it gives a $1 discount to purchase the ride at $8 or $9. The TILT was quite fun but it was more scary than it seems. It leans outwards towards 45 degree or so over an impressive view of Chicago City. It feels like holding the low plank in a Chaturanga pose over a glass on 94th floor.

Me on the TILT ride with trembling hands
360 Chicago is quite empty at 9pm, which is pleasant to sit around and take in the view.
The Ferries Wheel at Navy Pier switches off somewhere before 9:15. This picture was taken at 9:08pm and the wheel was no longer visible after 9:15pm.

Field Museum

I had very high expectations of the Chicago Field Museum, after reading the reviews and also having visited a great Natural History Museum in UK Newcastle few months ago, and it did not disappoint too! My favourite exhibition was the Griffin Hall of Evolving Planet, where it takes you through the geological time scale and the Mass Extinction events which precedes a new era. You can also find SUE, the largest T. rex fossil ever found in this section. I walked through this section several times, because the first time through there were some kids on an excursion and I could not fully enjoy the exhibits. Being with screaming kids in a small enclosed space can drive you crazy.

SUE, the largest and most complete T-rex fossil ever found

I spent 6 hours in the museum, even though I did not watch the movies! That was partly attributed to the initial haphazard routes I took to avoid the school kids. I had lunch in the cafe too, and it was decent and not too expensive. My Go City pass included one special exhibit, which I chose the “Life after Death”. It was not interesting though, I don’t know about other exhibits but if you had to choose you can skip this.

Adler Planetarium

I visited the Adler Planetarium on a Wednesday, where the opening hours was from 4pm-10pm. One reason I wanted to visit the Planetarium was because of a Mars Occultation event where the Mars would disappear behind the Moon and reappear one hour later, and there was a live-viewing event on that day. However, it was a cloudy night and we did not get to see it live. Instead we watched on youtube which streamed live from Griffin Observatory at Los Angeles.

The Go City Pass comes with two sky shows to choose from, of which I chose the “Planet Nine” and “Destination Solar System”. I enjoyed both the shows very much, especially Planet Nine. I was quite tired after the visit at Field Museum, so the exhibits did not leave a deep impression.

I did not visit the Doane Observatory because I wasn’t issued an entry ticket during registration, and I was not sure if I could still come back in for my show if I went outside. However I read that there is a nice view of Lake Michigan and the Chicago skyline up there.

Hop-On-Hop-Off Bus

I decided to try out the Hop-On-Hop-Off bus since I had an extra attraction to choose from, but I regretted it very much. The bus frequency was 30 minutes and there is a schedule at the bus stops to board from, but the bus can not come and skip a scheduled run. The customer service was unhelpful as well.

Do skip the Hop-on-hop-off bus in Chicago because the bus and metro systems were quite decent, compared to many other USA states. The day pass cost $5 for both the metro and the bus. In fact, the bus route 146 is so similar to the Hop-on-hop-off bus route that you can use it as the sightseeing bus instead, and the frequency is better and a lot more predictable.

Other Things I did at Chicago

I visited the Medieval Torture Museum, which is worth a visit especially if you watch horror movies. For example, you can see the Pendulum from the SAW movie. The museum was decorated with elaborate details, and there is a ghost-hunting game at the end which was quite fun. I recommend bringing along a earpiece and powerbank because the audioguide is played on your phone. WIFI is provided. 1 minute walk from RTA Lake Red Line.

I visited the Navy Pier but it was surprisingly empty the day I went, felt like a ghost town! It was the day that the Shoreline Sightseeing booth was also closed so I could not take the Architecture River Tour from there. I’m not sure if it is normal.

One of my favourite way to explore a city is to spend an aimless day around and see how the day unfolds. I visited a German Christmas Market called “Christkindlmarket” and tried a hot spiced apple cidar with a 25th anniversary souvenir mug. It tastes like hot cinnamon with apple cidar, and feels good to drink in the winter.

The guided tours from the River Tour and Hop-on-hop-off bus mentioned the Chicago Hot Dog and Deep Dish Pizza, so I thought of trying out one of them. One thing they emphasized was that you should not take Chicago hot dog with ketchup, you would be frowned upon. I later found out that the Chicago Hot Dog contains beef which I do not take, so I tried the Plant-based Garden Dog from Portillo’s Hot Dog. It was quite tasty.

I fell sick on the day I arrived Chicago, so I slept a day away. I missed an investor meetup and cashflow game that I signed up for. However, I was grateful that I recovered quickly and managed to have some fun in Chicago. This trip was a very last-minute trip so most of my itineraries were planned in Chicago itself, which was not optimal but good enough.