72 Hours in Chicago

Where did I go: Chicago, Illinois, USA

When did I go: July 2015

Friday – 3rd July

0905: Landed in Dublin, on my way to Chicago. Dublin airport has US pre-clearance, which means that you go through US customs and immigration before boarding a plane to US. This seems like a great idea. Transit passengers have a couple of hours to wait around anyway and now you can put that waiting time to good use.

1130: On board Aer Lingus. First time I’m flying with this airline. The plane is an Airbus A330 in a 2-4-2 configuration. Food is acceptable. Alcohol is not free. Selection of inflight entertainment ok, but not as a wide or up-to-date selection as you would get from some of the more up-market airlines. However, on this 7 hour flight I manage to watch: The Second Best Exotic Marigold Hotel, Jupiter Rising, Kingsman and When Harry met Sally. Two out of the four films (Jupiter Rising and When Harry met Sally) have scenes set in Chicago, which reminds me how much of a popular destination it is for film makers.

1334:  Landed in Chicago, Illinois.

1345: No immigration, no customs. It’s baggage claim and straight out of the door. Now, this, I could get used to.

1412: With some help from the friendly official on the platform, I get on the CTA (Chicago Transport Authority) train towards the city.

1600: Arrive at our home for the weekend. It’s an apartment in a waterfront high rise and has great views. We are on floor 29 and onto the right you can see Lake Michigan and the Navy Pier and on to the left,  many Chicago skyscrapers. At the bottom, the green Chicago river flows by. A fantastic location.

1630: Walking down the magnificent mile. Incredible collection of buildings, both old and new.

1715: Walking all the way down magnificent mile (actually 7/8ths of a mile according to the tour guide) brings you to the water front of Lake Michigan. The water goes on all the way to the horizon and its easy to forget that this is only a lake. There’s the man-made white sandy North beach – with people sunbathing and paddling in the water. We walk South along the water front. Many others are doing the same. Some are cycling and others on peddle carts. There are many boats, cruisers and yatchs out in the water. Each with dozens of people on board, with music blaring. It’s the start of July the 4th weekend!

1730: Arrive at the South beach – like the North beach, its entirely man-made. We paddle in the water for a bit, but the water is freezing.

1745: Walk back to the apartment along the river.

2100:  A quick dinner, and I’m done for the day.

Saturday – 4th July

0300: Suddenly woken by a noise that sound a lot like  gunshots – it carries on. I take a quick peek out of our 29th floor window. Somebody is setting off fire works on the other side of the river. Grrrr! Back to sleep.

0915: Started our city tour with the big tour trolley company. Along the way we see many famous Chicago landmarks and start to put names to the buildings we saw yesterday. The Wrigley building, the Water tower, John Hancock building, Drake hotel and many others.

Interesting fact of the day: the Wrigley building and the Wrigley field are both named after the chewing gum magnate William Wrigley Jr. In 1892, William Wrigley started to give away packets of chewing gum in cans of baking soda, only for the gum to become more popular than the baking soda.

1100: At the world famous Sears Tower – only it is not the Sears tower anymore, but the Willis tower. London based insurance firm Willis became the main tenant of the tower in 2009, giving them the right to rename the tower. But as the tour guide on the bus said, to Chicagoans “it’ll always be the Sears Tower”.
With 108 floors and 527.3m height to the top of its highest antennae, it is the 2nd tallest structure in the US and the 12th tallest in the world.

1215: After much queuing and waiting and buying our tickets, we are shown a 9 minute film about the tower. Then it’s a bit more queuing and we are whisked upto floor 103 in one of the fastest lifts I’ve ever been on.  The observatory deck on floor 103 offers great views – specially to the south and east. Although sunny, it is not the clearest of days so it is not possible to see very far.

On the west side of the floor there is a glass ledge that protrudes outward and you can walk on to it. There is much queuing here too. 

1330: Back down to ground level. For lunch we head over to Giodarno’s , Chicago pizzeria chain. There is a 45 minute wait for a table, so we book a table and order the pizza at the same time. So by the time the table is ready, so is the pizza. We have a signature Chicago deep dish pizza. It’s really more of a giant quiche with lots of cheese. The frozen strawberry lemonade is very nice though.

1500:  Lunch over. Back on the tour bus and we take the North city tour. This takes us through some nice areas, past the Lincoln Zoo and lots of green spaces, full of people celebrating 4th of July with picnics and barbecues. The highlight of the tour is the Wrigley field – the home of the Chicago cubs baseball team. There’s a game on today, so the whole area is packed. Residents in the nearby neighbourhoods are standing outside advertising parking spaces for $40.

1645: Finished with North city tour and walking down the magnificent mile. Pop in to the Hershey store, which is on the ground floor of the Hershey building. The front façade of the building is meant to look like a Hershey bar.

1835: Head over to navy pier for our fireworks cruise. It is extremely busy. Bags are searched on entry and there is a visible police presence. We head inside to get some food, but its hopeless – it’s completely packed with people and you really can’t move.

1925: Got some Aunty Anne’s pretzels with great difficulty. Head back to the queue for the cruise.

2025: We’ve boarded the shoreline fireworks cruise and it’s just about to push off. All of a sudden, there is screaming and people running away on the pier. It stops after 30s or so, but no one seems to know why. The boat crew however decide to push off and head out into the water.

2045: Out on lake Michigan now. The view of the Chicago night skyline from the water is superb. There are many boats out on the water, from very small dinghies carrying a family of four to three deck yachts hosting 4th July dinner/dance cruises.

 2120: Almost time for the fireworks. The captain of our boat finds a nice spot and drops anchor. Many other boats are doing the same.

2130: And off we go – I’m watching July the 4th fireworks in Chicago!!! 

2145: Fireworks over. Big applause from everyone and all the boats sound their foghorns.

2200: Boat docks at the navy pier. We disembark and join the sea of people leaving the pier.

2230: Back to the flat after another great day in a great city!

Sunday – 5th July

1000: Getting ready for my 2nd full day in Chicago. Quick browse on the internet tells me that the screaming and running on the Navy Pier last night was due to someone letting off a firework inside the restaurant.

1145: On a tour of the Greek town and Little Italy suburbs of Chicago. On the way, we see where the famous 1871 Chicago fire supposedly started – in a farmer’s barn. The story is that a cow kicked a lantern, which set fire to the hay. This started a fire that went on for 3 days and burnt down 90% of the town. The water tower and water palace are the only pre-fire buildings which are still standing. But, every cloud has a silver lining and the outcome of the fire is the well planned city we see today. In fact, it is so well planned, that there are upper level roads and lower level roads. The lower roads lead to basements of buildings for deliveries and services etc. leaving the upper level roads free for access.

1215: On tour in Greek-town and Little Italy – it’s not the most well to do area of town. The tour guide tells us that the great fire did not spread this far, so most houses in this area date from before the fire. There are many murals as well.

1245: On tour of South side of Chicago. This is a leafy green well-heeled area of Chicago. We also see the Chicago residence of Michelle and Barack Obama. There is a heavy Secret Service presence all around the house and the tour guide tells us that cars cannot be parked in the vicinity. Infact, event the tour bus is not allowed to hang around for more than a minute or two.  The Obama house is a stone’s throw from the home of Mohammed Ali.

Home of Mohammed Ali

1330: After a quick stop at the museum of science and industry, we head back to the city. There’s lots of traffic as many cars are heading to the (supposedly the last ever) “Grateful Dead” concert at Soldier Fields stadium.

Museum of Science and Industry

1400: Starting to think about lunch. I really want a Chicago hot dog, but being a vegetarian, I’m looking for a veggie version, which is hard to come by. We see a hot dog stand on the side of the road and ask the lady whether they do  a vegetarian version of the hot dog. “Of course” she says. “Great. What’s in it?” I ask. “It’s the same as the normal hot dog, but with just the vegetables” comes the reply. Okay. Think I’ll pass on that.

1430: (Temporarily) given up on the quest for a veggie hot dog and having lunch at Corner bakery cafe. Good food, nice atmosphere. Even more “deadheads” heading toward Soldier Fields.

Soldier Fields Stadium and traffic going to the Grateful Dead Concert

1530: Walking around the Millennium park, which is sandwiched between lake Michigan and the city front. There are a number of fountains and artworks scattered around – The Cloud Gate (aka Chicago Bean) is by far the most popular.

The Chicago Bean

1930: Dinner at Cheesecake factory. I’ve been wanting to give this place a try ever since I first watched The Big Bang Theory. The menu is massive – about 15 pages. Portions are huge. Even sharing the starter, I can’t finish the main course (a veggie burger). There is absolutely no room for desserts, but I’m not giving up. We’re having the strawberry cheesecake and peanut butter cheese cakes “to go”.

Desserts “to go”

2130: Dinner finished just in time to catch the Chicago city night tour. The tour takes almost the same route as the day tour, but by night, it’s a different city. Many of the tall skyscrapers are lit up for the 4th of July weekend in red, white and blue; and even with one cheering on the US women’s football team who are playing Japan with Ladies football world cup final.

 2300: Night tour done, and so am I.

Monday – 6th July

0900: My last day in Chicago 😦 Walking to Navy pier.

0950: At Navy pier. It’s practically empty and a lot more enjoyable without the crowds. Many yachts and cruises are docked along the pier. What catches my eye is the “tall windy”. A pirate ship with real sails. You can get a ticket for $30 for a tour, but there’s no time to fit that in today. Need to add it to the list for my next visit.

The Tall Windy

1130: Lunch. Finally! A Chicago (veggie) hot dog. A Chicago-style hot dog will contain: a Vienna beef frankfurter, a poppy seed bun, two tomato wedges, yellow mustard, relish, chopped onion, a dill pickle spear, two Vienna sport peppers, and a dash of celery salt, but NO KETCHUP (a key feautre of the Chicago Hot Dog).

What a Chicago hot dog is supposed to look like

We find the veggie option in the “American Dog” takeaway in the navy pier, and I have to say it looks reasonably close to the one in the advertising. Tastes great too!

What a Chicago hot dog actually looks like

1230: Walk back to the apartment and pack bag. Time to head home.

1315: Get the blue line metro to O’hare airport.

1400: Arrive at O’hare.

1430: Checked in.

1500: Massive queues at departures.  Any longer here and I’m going to miss the flight.

1700: Flight takes off after 1hr delay. Goodbye Chicago, can’t wait to see you again.

Linking to:

Packing my Suitcase




  1. A great time to visit Chicago! You certainly saw a lot of the city. I would love to revisit in the summer (it’s pretty cold in winter). The cheesecake factory portions are ridiculous! It’s pretty good food though. Thanks for linking to #citytripping

    Liked by 1 person

    1. I had hear that summer is a great time to visit, as there’s lots going on. I enjoyed my first visit to the cheesecake factory. Thanks for stopping by and commenting! #citytripping


  2. I really want to visit Chicago- topping my list after having been to San Francisco, so this is a great starting point for a long weekend. It must have been incredible to visit on July 4… though busy. And such a good idea to go through immigration in Dublin rather than on arrival. #citytripping

    Liked by 1 person

    1. July the 4th was busy, but not too bad. I loved going through Dublin, such a timesaver when you arrive! Thank you for stopping by and commenting #citytripping


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