Finally I’m posting some travel tips and pics for America. Read about New York, Boston and Philadelphia first!

I had a great couple of days in the Windy City. I found it prettier, more characterful, less blocky and less claustrophobic than New York. My top 5 must-sees are marked with a ⭐

Millennium Park & the ‘Bean’ ⭐

Millennium Park is in the centre of Chicago and a good place to start, as it houses the iconic ‘Bean’ or Cloud Gate. Walk around it and see the sky, skyscrapers and yourself beautifully reflected. Make your way through the park towards the Art Institute of Chicago and you’ll find the Floating Walkway going up to the museum (great views). At the top was this sculpture, Bronze Bowl with Lace, like a striated tree with a sheeny green-brown surface. Top marks for the public art.

The Bean

Lakefront Trail & Lake Michigan ⭐

Take the Lakefront Trail northwards from the seafront at Grant Park, and turn in when you get to the river (where the Riverwalk starts). It’s a short walk in a lovely green area with great views of the Chicago skyline, the harbour, and Navy Pier.

Dusable Harbour
Why are there no boats, you say? Look closely and you’ll see that’s ICE. For 20 feet out.

The Loop seen from the Lakefront Trail. More ice!

Riverwalk ⭐

The Riverwalk runs along the north side of the Loop. Incredible vistas of the Chicago architecture and the identical metal bridges from a lovely clean waterfront walkway. The corn-on-the-cobs in the picture below are Marina Towers, the first cylindrical apartment buildings ever, built in the 60s.


The Loop ⭐

The Loop is downtown Chicago’s business centre. It has pretty buildings and more cool public art, like this flamingo sculpture, and the unnamed ‘Chicago Picasso’ nearby.

The Flamingo
I’m cheating with the pictures below, because they’re actually taken just north of the Loop on the north side of the river, just at the start of the Magnificent Mile. The Wrigley Building, with its oh-so-cute diagonal bridges, was built in 1924 as a HQ for the chewing-gum company, and the Tribune Tower opposite, with its beautiful Gothic-imitation details, was completed a year later to house the Chicago Tribune. But they give you a feel for downtown Chicago.

Magnificent Mile

Wander northwards from Tribune Tower for high-end shopping, restauration and hotellerie, and landmarks such as the Chicago Water Tower, an incongruous castle-like structure that looks like it was made on Minecraft.

Water Tower

Willis Tower ⭐

No city break is complete without a trip up a skyscraper, right? New York has Top of the Rock and the Empire State, Chicago has the Willis Tower (sometimes still known as the Sears Tower). It was the tallest building in the world on completion in 1973 and houses the Skydeck observatory on the 103rd floor. You have to pay and queue, but it’s worth it for the views:


View from the Willis Tower
It’s funny how proud cities all are of their scrapers, charging you for the view and making it into a sort of ritual, a guided procession between the ticket hall and the lifts. Then there’s the incessant competition over size … 

Museum of Contemporary Art

Not far from the Water Tower is this modern art museum, which houses fun pieces such as a giant fabric fried egg slapped onto the floor, that famous sofa that looks like a pair of cherubic lips, and some Andy Warhols.

Holy Name Cathedral

Also near the Water Tower is this cathedral, which I stumbled across by chance. It’s beautiful and unusual inside, with a wooden ceiling, a beautiful organ, a cell-like glass back wall, and modern stained glass. A feast for the eyes!

Navy Pier

Event venues, restaurants, an IMAX, a ferris wheel … Navy Pier is the slightly tacky entertainment hub of Chicago. My favourite part of it was the view out to the abandoned Chicago Harbour Lighthouse illuminated in the pinky-blue twilight.

The lighthouse from Navy Pier

Roscoe Village

I stayed in Roscoe Village, a suburb on the Brown Line. Chicago doesn’t have a subway, just ‘the L’, a number of elevated train lines running in from the suburbs towards the Loop. Above the suburban houses, under the clear sky, the receding tracks held a certain promise and excitement …

Since I’d stayed in the Upper West Side in NYC, I hadn’t seen an American suburb before. I think I was expecting a Desperate Housewives situation. Instead of white picket fences, I found grid upon grid of large detached homesteads with a few features in common:

  • Elevation: front doors were as much as a whole storey off the ground. Does it flood a lot here?
  • No garden! Just a patch of ‘yard’ around the house, built slap bang in the middle of the plot
  • Every front door has a porch, sometimes even a terrace
  • Gables!
  • Slatted wood!


And I don’t know anyone in Britain who would fly the Union Jack outside their home …

That’s all for Chicago: stay tuned for Miami & Florida Keys!


2 thoughts on “Chicago

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