Chicago, Illinois, the starting point of the classic road trip, Route 66. Over 2400 miles of historic Americana running from the corner of Michigan and Adams through 8 states to the warm shores of Santa Monica California. We completed the drive over 3 weeks during the summer and as soon as the opportunity arises, we’ll be doing it again, this time from the west back to Chicago.
As well as the start of Route 66, Chicago was also the final destination to many Africa-Americans heading north in search of better lives. This time on another classic road, Highway 61, ‘The Blues Highway’. The migrants brought their traditional music with them which developed into the distinct ‘Chicago Blues’ style and artists such as Muddy Waters, Buddy Guy and Howlin’ Wolf.
So, before you embark on your great American road trip make sure you allow time to explore the ‘Windy City‘ itself and soak up its unique culture and identity. We had a couple of days before our road trip began so here is what we got up to during our short stay in Chicago.
Cloud Gate And Millennium Park
Cloud Gate or as it is better known ‘The Bean’, the remarkable and very popular public sculpture by artist Anish Kapoor. Movie fans will recognise it from many films including the 2011 sci-fi thriller starring Jake Gyllenhaal, Source Code.
You can find the sculpture in Chicago’s Millennium Park, a relaxing green oasis in downtown Chicago. As well as gardens, outdoor art exhibitions and play areas for kids the centrepiece of the park is the Jay Pritzker Pavilion designed by the renowned architect Frank Gehry. If you’re visiting in the summer months try and catch one of the outdoor concerts. One of the highlights is June’s Chicago Blues Festival with stages around the park and headline acts performing at the Pavilion.
The Art Institute Of Chicago
The Art Institute of Chicago is one of America’s oldest and largest art museum, we spent 3 hours there and only saw a fraction of the collection. However, we did get to see the instantly recognisable ‘American Gothic‘ by Grant Wood. The classic painting first came to our attention when it was recreated at the start of the Rocky Horror Picture Show.
The institute is also home to the greatest collection of Impressionist art outside Paris, it includes paintings by Renoir, Monet, Seurat, and Van Gogh.
The Chicago Architecture
A large part of Chicago was destroyed by fire in 1871, the resulting rebuild created a unique opportunity for architects to experiment and make their mark. One of the world’s most famous architect, Frank Lloyd Wright started his career in Chicago when he arrived in the city in 1887 to look for work in the rebuild.
Chicago was the birthplace to the skyscraper and driven by an unofficial competition with New York the city’s skyline continues to grow. The two cities account for more than half of America’s tallest buildings. Chicago is home to the Willis Tower (still better known by its former name, the Sears Tower), the 1920’s neo-Gothic Tribune Tower and the Wrigley Building. The Chicago Water Tower is also worth a visit, it’s one of the few buildings to have survived the 1871 fire.
We recommend taking a guided Chicago boat tour along the river. We found it a great way to view the architecture and to see many of these iconic buildings without having to walk miles.
The Willis Tower Skydeck
With all these incredible skyscrapers around you at some point, you have to go up one of them. From the 103rd floor of the Willis Tower, you can enjoy a 360-degree view of Chicago and apparently 4 states. Although the visibility wasn’t brilliant during our visit it was still an amazing sight and for those who aren’t too afraid of heights, try the ‘Ledge’. This is a glass-floored balcony which looks straight down 1,353 feet to the streets below.
Another great view can be found from the observation deck of the John Hancock Center, they also have a cocktail bar where you can sit back with a drink and enjoy the sunset.
Chicago Food
From classic Italian food to all-beef hot dogs and of course, the famous Chicago Deep Dish pizza, there is plenty of hearty comfort food on offer. They certainly like their meat in Chicago, after all, it is the meatpacking capital of the USA. For a reasonably priced meal which you can easily share between 3 or 4 of you, try a large deep dish pizza from Chicago’s own Lou Malnati’s.
Also, as you would expect from America’s second city, there’s no shortage of fine dining restaurants and cool cocktail bars.
One place to try before you embark on Route 66 is Lou Mitchell’s diner on Jackson Boulevard founded in 1923. It may be a bit touristy but it’s a definitive part of the Route 66 heritage. In 2006, it was listed on the National Register of Historic Places.
Why not see how we got on, you can watch the whole of our Route 66 trip from Chicago to LA here.
ashleigh allan
April 1, 2020 at 4:33 pmLooks a great place!
Mr and Mrs W
April 2, 2020 at 9:51 amIt was, wished we had more time.
Susan B
April 1, 2020 at 5:18 pmI had no idea that Chicago marked the start (or end) of Route 66. An interesting city. Hope to visit one day. Thanks for the informative post.
Mr and Mrs W
April 2, 2020 at 9:53 amYes, there’s always plenty of people taking photographs of the Route 66 start sign.
Fiona jk42
April 1, 2020 at 9:19 pmIt’s odd how your feelings about a city can forever be coloured by experiences you had there. I lived and worked in the US for almost 12 years, and have really unpleasant memories of being in Chicago in the middle of winter, working with a really unpleasant client. As a result if asked I always said I hated Chicago. Then about 5 years ago, I had to go there for business again. This time it was summer, and although the client was again someone I didn’t like, the other people I was working with were great, meaning I came away with a much nicer feeling about the city.
Mr and Mrs W
April 2, 2020 at 9:55 amSame feelings for us about London but we love going there now.
Years ago we used to live there in a really horrible place, damp, no money and a dull job and hated the place.
Jayne Townson
April 5, 2020 at 2:56 pmWow, some fantastic photos there, looks like you had a lovely time.