Chicago
Two days in the Windy City
It was just a short stop on Charlie’s trip around the states and she only had two days in Chicago. She arrived on a Saturday morning after a night on the train at Union Station. She brought her luggage to a shop that offered hourly storage and walked over to the stop for the Hop-on-hop-off-tour in front of the Willis Tower. She was lucky and there was immediately a bus available. She had booked her ticket online in advance.
Big Bus Tour in Chicago
Hop-on-hop-off-tours are probably the most touristy thing one can do anywhere in the world and it usually is the most efficient way to get an overview of everything there is to see and a first impression of a city.
The Willis Tower was already the second stop of the bus; the first stop is by the river front in the heart of the city. The bus drove from the Willis Tower further down towards Millennium Park and Charlie got a first glimpse over the iconic overground trains that mark the city centre, also called “The Loop”. The bus also passed by the Federal Reserve which houses the Money Museum. Entrance is free.
From the bus, Charlie spotted the Millennium bean in between the trees and got a good view of The Art Institute of Chicago as well as the skyline. The route led further on towards the Planetarium and the Aquarium from where Charlie had a good view over Lake Michigan and the sailing boats. The weather was still warm like summer days in early October and a lot of sailing boats were out on the lake. Charlie enjoyed the open top bus, although she quickly noticed why they call Chicago the “Windy City”.
The bus drove along the lake towards Navy Pier and then back into down town. It crossed one of the many bridges, drove along the Magnificent Mile, a paradise for anybody who loves shopping, and passed by the Chicago Watertowers, the only two buildings that survived the Chicago Fire in 1871.
The last few stops of the bus were near the Hard Rock Café and River North, a popular outside dining part of Chicago. Charlie then stayed on the bus as it started another loop and since she still had some time until the time of her booking at the Willis Tower, she decided to get off at Millennium Park to see the Bean from a bit closer. There were a lot of people though and Charlie only got some snapshots and moved on. She walked from there to the Willis Tower.
Chicago – the city of sky scrapers
Before the Chicago Fire in 1871, the city was built out of wood which had disastrous consequences. After the fire, it was a clean canvas and was completely rebuilt from the ashes. The World Fair in 1893 was another opportunity to give this city an iconic skyline and Chicago became the birthplace of the skyscraper. If you’re interested in architecture, you can do a river cruise where they tell you everything about the downtown architecture where no skyscraper looks like the other.
Willis Tower
Charlie had booked for that afternoon a ticket for the Willis Tower (formerly Sears Tower). You can get tickets there, however, they are for a particular time slot. So if you want a specific time, you should get your ticket online.
At the bottom of the tower is an interactive experience that presents the history of Chicago and shows all the sights and landmarks worth seeing. You could also take a selfie with some of Chicago’s most favourite sons and daughters, e.g. Barack Obama, Michael Jordan and Oprah Winfrey. There is also a video explaining the architecture and particularities of the different skyscrapers.
You then take an elevator up to Skydeck on the 103rd floor. You can see Chicago from above in all 4 directions and step onto one of the famous ledges that make it look as if you’re floating in the air. There is a separate queue for the ledges and you only get 90 seconds because they are so popular. The photo is worth the wait though.
Depending on how intensely you take the interactive experience in, you should plan 90 minutes to 2 hours for your visit at the Willis Tower. At the entrance to the building is a food court too in case you want to get lunch.
Chicago River Cruises
If Charlie hadn’t had spent the previous night on a train and was desperate to wash her clothes, she would have booked a Sunset Cruise on the Chicago River for that first day. That seems to be a popular activity. There are multiple tour providers you could explore the river with at any time during the day. You can also choose between an architecture tour, a simple River Cruise or a party boat. You could also hire a smaller boat, a bike boat or a kayak. The latter also offers guided tours.
If you don’t want to get on the water, you can enjoy the river from the River Walk. There are also plenty of bars and restaurants. Charlie had lunch there on her second day in Chicago.
Chicago – the city of gangsters
Apart from the iconic skyline, there are other things Chicago is known for: Al Capone and the musical and film “Chicago”. There are two different tours offered that show this aspect of the city, a bus tour and a walking tour. Charlie had booked the walking tour for the afternoon on her second day in Chicago. In the morning, she did a street art tour and she walked along the river to get lunch in between.
The Gangsters & Ghosts Walking tour started close to the river walk opposite the spot where the Big Bus Tour would take off too.
Al Capone in Chicago
The recurring theme throughout the tour was, of course, Al Capone. The son of Italian immigrants had grown up in New York and was exposed to the scene early on in his life. He learned the “business” guarding the doors in brothels before Johnny Torrio took him to Chicago to support the business activities in the Windy City. It was the time of the prohibition and there are several stops along the tour where the guide points out places, often in the upper floors of skyscrapers, where Al Capone ran a speakeasy. The tunnels below the city were used for alcohol smuggling.
Other stops along the tour often refer to the rivalling Irish-polish gang in Northern Chicago and the Italian gang under Al Capone in the South. There have been incidents of shootings and murder ultimately leading to the Valentine’s massacre.
The Palmer House Hotel & Chicago Broadway
Not far from the River Walk is the theatre district of Chicago where one can enjoy some great Broadway productions. Unfortunately, a great tragedy happened in this location in 1903. A fire at the Iroquois Theatre (today the Nederlander Theatre) caused more than 600 deaths and gave the small alley the name “Death Alley”. This tragedy also led to the modern health and safety protocols for entertainment venues, starting from seat assignments and maximum occupancy, to push bars on doors and fire escapes.
Across the street is the Chicago theatre, showing the name in flashing lights for all to see. This made Charlie think immediately of the movie “Chicago”. The story is based on real events: A prostitute who had shot her boyfriend and got off with a slap on the wrist. The bullet holes can still be seen at the Palmer House Hotel. The interior reminds of a majestic hall and you can go inside and enjoy a coffee even if you’re not a resident of the hotel. Whilst you’re already on it, you should also try a brownie. After all, it is the place where the brownie was invented.
The Gangsters & Ghosts tour finished near the Buckingham Fountain and it was about 30 minutes before sunset. Charlie walked over to the waterfront of Lake Michigan to catch the evening light. The sun sets behind the skyscrapers in the other direction. The light over the lake is still amazing though and the foot- and cycle path invite for a stroll. Charlie followed the path back to the River Walk and took a bus to her accommodation from there. If she had had more time in Chicago, she probably would have hired a bike or a Segway to explore more of the waterfront trails.
Accommodation and public transport in Chicago
As in any big city, downtown hotels are a pricey option. Charlie stayed at Chicago Getaway Hostel where you could stay in a shared dorm or get your own room. They serve breakfast, and, what made Charlie the happiest, they have washing machines that are free to use for guests. The hostel is near Lincoln Park in the North of Chicago and it took by bus about 30 minutes into the city centre.
To get to the airport, Charlie had to take a bus and then the blue line which took a little over an hour.
Public transport is very affordable in Chicago. You can get a 24-hour-ticket for USD 5 at any of the ticket machines at the train line. A single ride costs USD 2.50. You could tap your debit card, however, that wasn’t working for Charlie on the bus because her card isn’t connected to a US-bank-account. If you plan to take the bus whilst in Chicago, it is best to get a Ventra card right away. There are ticket machines at the airport too.
