A Flying Visit to Chicago

by | Destinations, USA | 3 comments

We just flew in from the windy city….! Actually, Chicago was not so much windy as freezing cold. Bright blue skies, fabulous sunshine, but teeth-clenchingly cold! And we did not fly in for this flying visit to Chicago; we drove!

I had preconceived ideas about Chicago before we visited. First up were the crime and the murders which feature so much in the press these days; secondly, I tended to think of prohibition, Al Capone and Eliot Ness; and then of course, there was Doris Day on a mission to the windy city!

What I found was a shiny, modern city with futuristic and beautiful architecture, great character and fabulous food. I know that there are problems, but in downtown Chicago where we stayed for the 36 hours we were there, we saw none of this. In fact, we felt very safe wandering around. Chicago exceeded all my expectations as a city to explore.

View of Chicago

The city viewed from the Chicago river

Two Days in Chicago: where to go, what to see, advice and top tips

This visit to Chicago really was a whistle-stop tour though: we had two days. We had delivered our campervan to Elkhart, Indiana to have the troublesome slide fixed and took the opportunity to drive the hour and a half to visit Chicago whilst it was in the workshop. Once there, the hire car stayed in the parking lot for the duration and we walked everywhere.

So what did we see during our two days in Chicago?

Lake Michigan

That is a little obvious really, but it would be a shame to visit Chicago without checking out the Great Lake on which it sits. Chicago sits on the shore of Lake Michigan, the only one of the Great Lakes to be located in the USA in its entirety. The lake is enormous, of course, so the city feels like it is on the coast. This adds to its appeal in my view. With the piers, the harbours, the marinas, the boats and the beaches, it feels like a seaside town. (I have checked incidentally…..the lake is definitely a lake and not saltwater!) There are some lovely walks along the shore of the lake in the city.

Chicago skyline

The Chicago skyline viewed from Lake Michigan


The Chicago shoreline

Chicago Architecture

After the lake, the other standout feature of Chicago is the architecture. It has a planned, organised feel to it in the way it has developed over time. The buildings all fit together in a beautiful mosaic of glass and steel. They have stretched higher and higher over the years, but most of the buildings are not featureless concrete skyscrapers as one often finds in cities; they are imaginative, attractive and quirky. Some are like giant Jenga constructions; others are wavy and elegant, including the multi-storey carpark near our hotel. Even the Trump Tower is beautiful, though it pains me to admit it.

Parking lot

Even the car parks are imaginative in Chicago

Trump Tower

The Trump Tower seen from the Architectural Tour Boat

Trump Tower

Trump Tower by night

A River Cruise

We took the Architectural River Cruise on the Chicago River through the centre of the city. This opened up a different perspective from that observed on the street. I would highly recommend it. The tour lasted an hour and a half and the guide was very informative, pointing out the various architectural styles and how they had changed over the years, as well as providing some of the background stories.

Top Tip: there is a Groupon voucher for the Architectural Tour. This offers a fairly significant saving (34%), but don’t wait until you actually arrive at the ticket office before downloading it as we did. We almost missed the boat – literally!

The Magnificent Mile and the Hancock Tower

Most of our exploring was on foot and we found Chicago to be a great walking city. First up was the Hancock Tower on the Magnificent Mile (downtown Chicago’s premier street). The Hancock Building has 100 floors, but is only the third tallest building in Chicago (and it is likely to be demoted fairly soon as more building takes place). There is a 360 observation deck on the 94th floor. We had to check it out, but fortunately, there is a super-fast lift to get there – and a cocktail lounge waiting at the top! The views are superb, especially when it is as clear as it was the day we visited.

Hancock Tower

Cocktails at the top of the Hancock Tower

View from Hancock Building

The view from the 96th floor of the Hancock Building

View from the Hancock Building

And from another direction!

The Tilt

“The Tilt”! Get a different perspective as the windows tilt out over the street far below

Our exploration continued at the bottom of the Hancock Tower in the Cheesecake Factory. We were hungry, it was there and we are  great fans of The Big Bang Theory so in we went! Inside it was decked out to look like  visitors were in a giant cheesecake, but it reminded me of Jabba the Hutt! The Cheesecake Factory is an American Chain, but the food was great – and we ate rather too much. I had a burger (I love burgers in the US!) and Peter had crispy roast Brussel sprouts (?!) and tuna tartar. We were too full for cheesecake.

Cheesecake Factory

Lunch in the Cheesecake Factory


Navy Pier

We went down to the shore and wandered along Navy Pier. Originally called Municipal Pier, it was re-named in honour of the naval veterans after WW1. With shops, exhibitions and other attractions, I imagine it is very busy in warm weather, but on this cold, sunny day, it was quite empty. The Centennial Wheel, a giant ferris wheel, was running and I think it offers great views over the city and Lake Michigan, but we did not go up on this occasion.

Nave Pier

Taking a seat on Navy Pier

Millennium Park

One of my favourite places on this visit to Chicago was Millennium Park. It is in the middle of downtown Chicago and is adorned with beautiful sculptures and architecture. The most eye-catching is Cloud Gate, also known affectionately as the “Chicago Bean”. No visit to Chicago would be complete without visiting the Chicago Bean!

Cloud Gate

Cloud Gate in Millennium Park

This beautiful piece of public art by Anish Kapoor is interactive in that the observer becomes part of the sculpture, reflected in its seamless, polished, mirror-surface, along with the Chicago skyline. Visitors can walk around it and observe it from all angles, but one can also walk beneath and through it, still reflected in the surface above.

Chicago Bean

The “Chicago Bean”


There we are!

Under the bean

Under the bean


The skyline in the bean

Other pieces of architecture, the BP bridge and the pavilion, both designed by Frank Gehry, continue the theme of curved shiny surfaces and make this whole park unique and attractive. The pavilion with its ribbons of stainless steel curving high above, serves as an outdoor auditorium for concerts and performances.


The Pavilion in Millennium Park

The Pavilion

The Pavilion

The bridge, constructed from more stainless steel, provides a long, elegant, curvaceous pathway over the highway below. It is both functional and a piece of art.

BP Bridge

The BP Bridge designed by Frank Gehry

Eating out in Chicago

We really enjoyed the food in Chicago. I have already mentioned the Cheesecake factory, but that is not unique to Chicago. We had been told that any visit to Chicago must include Chicago Deep-Dish Pizza and that the place to go was Lou Malnati’s. So we went!

The place was heaving but there was a great atmosphere and we did not mind waiting the 45 minutes (plus) for a table. Still full from the Cheesecake factory, we were probably not in a position to do Chicago Deep-Dish the justice it deserved, but we ordered a small classic to share. We should have pre-ordered as the pizza then took another 45 minutes to prepare. Deep-dish pizza is very different from Italian style pizza in that it is more of a pie, albeit an open pie. The crust is firmer, more like a pastry and the cheese is on the bottom beneath the sausage and other toppings, the opposite of what we expect with traditional pizza.  Crushed tomatoes smother the top of the pizza.  It was very tasty, but would I order it over more traditional Italian pizza? Mmm…..Further taste tests required!


Chicago Deep Dish Pizza

We could not eat it all so took the remainder back to our hotel, thinking we might eat it the following evening back in the camper. Unfortunately, we put it in the drinks fridge ….. and forgot about it. Presumably it has been discovered by now!

The second evening we ate at Shaw’s Crab House and Oyster Bar. This, frankly, was wonderful. The seafood was superb. Peter had oysters, six different kinds, whilst I had a selection of shrimp, scallops and crabcakes. It was all beautifully cooked and absolutely delicious. The place was really busy again, but we got a table straight away and there was a great atmosphere, more so because of the 3 man blues band that was playing. A meal to remember.



Oyster Bar

Shaw’s Oyster Bar


And great music too!

Goodbye Chicago – you were great!

The phone call came the next morning to say the camper was fixed and ready for collection. That was the end of our two days in Chicago! We retrieved the rental car from the carpark where we had left it and headed back to Indiana. We enjoyed our flying visit to Chicago and would definitely recommend it as a city to visit.


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  1. This was great! I cannot wait to visit Chicago and get some of that delicious looking pizza!!!

  2. Fascinating report on a terrific city. Last year my boss left London to go and work there, so it must have a lot going for it.
    Crimes & misdemeanours… you forgot to mention the 20,000 deceased citizens who voted for JFK in 1960! And 30(!) years ago on my one and only visit, the hotel concierge very firmly told me to turn right, not left, when exiting the hotel!
    Safe travels!

    • Yes, I think Chicago has quite an “interesting” history!


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Hello!  I’m Jane. I live in the Lake District in the north of England with my husband, Peter. We love to travel, but this is a great place to call home.

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