My wife and I wanted to get out of town for a few days, and thought my birthday weekend would be a good opportunity. Now that we knew the when, we had to decide the where.

Last year my wife came along with me when I went to Chicago for a frequent flyers seminar put on by some of the experts from FlyerTalk. We were staying at an O’Hare hotel, but took the train to downtown Chicago one afternoon, saw some of the sites and ate some great pizza. We had such a good time that we decided the Windy City would be a perfect destination for us.

I began the planning process and found one problem with our choice of dates: the NATO summit was taking place in Chicago at the same time we’d be there. That might not only make it difficult for us to find a room at a downtown hotel, but there would also be thousands of protestors,, street marches, etc. We had enough of that in Rome last year and did not want to deal with it again. so we moved the trip back a week, arriving in Chicago the day after the end of the Summit.

We had an easy trip from Austin to Chicago, taking a non-stop flight that departed at 11:30 a.m. This was my first trip after earning Executive Platinum Status, my wife and I were both upgraded to first class. We had an uneventful flight (uneventful = good!) to O’Hare where we took a van to our hotel, the Chicago Wyndham, located downtown, just a block from Michigan Avenue and the Magnificent Mile.

Although I had no elite status with Wyndham they treated us well, giving us a room on the 16th floor looking out on downtown.

I’ve seen some reviews of the property on TripAdvisor where people complain about the hospital next door and the noise from the ambulances. All I can say to these people is that if they want a room with no noise, don’t stay in downtown Chicago. The noise of cars, trucks, and sometimes ambulances is constant — that’s what happens when you stay downtown in the middle of one of the world’s great cities. After the first night, we did not even notice the noise any more.

A Corner Bakery Café was located across the street from the hotel, and provided a n easy source to affordable food.

The location of our hotel could not have been better. We were one block from Michigan Avenue, just a few blocks from the John Hancock Tower, and walking distance to the Navy Pier.

We visited the Hancock Tower on our first day. The views are stunning.

The Chicago lakeshore, looking north from the Hancock Tower

Looking south towards the Loop area of Chicago.

We were fortunate to visit the Hancock Tower on a day with clear skies and breathtaking views. My goal, on our next visit, is to be in the tower at sunset and then see all the lights of the city come on.

We soon left the tower and took advantage of the wonderful weather to walk along Michigan Avenue, the Magnificent Mile.

We got as far south as the Chicago River, where we saw the drawbridge at Wabash Avenue had been raised to let some sailboats go through.


All traffic came to a stop on Michigan Avenue when they raised the bridge over the river.

That evening we went to dinner at Gioradano’s Pizza. Chicago is justifiably famous for its pizza, and Giordano’s is an excellent practitioner of the art. Chicago has two major styles of pizza: deep dish and stuffed crust. While the former is good, we much prefer the latter.

A slice of stuffed crust pizza at Giordano’s in Chicago.

The pizza at Giordano’s is delicious but very filling. We ordered their smallest pie, it came with six slices. Between the two of us we were able to eat three. The rest came back to the room and into the refrigerator. They were great leftovers the following day.

We got a great view of the Wrigley Building at night as we walked back to the hotel..

The next day we took an Architecture History Cruise of Chicago. This 90 minute cruise along the Chicago River highlighted the many architectural styles of the buildings along the river. That may be interesting to some, but not to us. We simply enjoyed a nice cruise around town on a beautiful day.

The Willis Tower from the Chicago River. At one time, the Willis Tower (originally the Sears Tower) was the tallest building in the world. However, it is now dwarfed by the Burj Khalifa in Dubai.

One of the recent additions to the Willis Tower is the Ledge, At 1,353 feet up, The Ledge’s glass boxes extend out 4.3 feet from the skyscraper’s Skydeck on the 103rd floor, providing never-before-seen views of the city. You can see people in the boxes, looking down on the city.

We passed the Chicago Merchandise Mart, said by some to be Chicago’s most historic building. Constructed in the late 1920s, It was the world’s largest building when it opened, with more than 4,000,000 square feet (372,000 square meters) of floorspace. The Merchandise Mart majestically sits in the heart of city on the Chicago River, anchoring the lively River North District.

One of our last views on the cruise before we returned to the doc near Navy Pier was the John Hancock Observatory that we had visited earlier in the trip.

After the cruise we visited the Navy Pier for dinner then returned to the hotel.

Our final day in Chicago was a quiet one. We visited Millennium Park to see the Bean.

The Bean in Millennium Park. I recently read an article that said that British artist Anish Kapoor, who sculpted it, hates the Bean name, and wishes people would call it by its official name, Cloud Gate. It weighs over 110-tons, and is 66 feet long and 33 feet high.

Under the Bean, looking up. The multiple reflective surfaces provide a variety of images.

We also had the chance to visit the Crown Fountain, which consist of two 50 foot towers, each covered with LEDs, which make is possible for them to display images of people’s faces.

One face on a tower at Crown Fountain.

Children play in the water,waiting for the fountain in the tower to spray them with water.

We waled back to our hotel along Michigan Avenue. The NATO Summit Conference had taken place in Chicago a week earlier, but there we still saw reminders of the conference.

US and NATO Flags flew along the Michigan Avenue Bridge.

Signs announced the Conference, even though it had been over for more than a week.

We got back to the hotel and started to pack for our departure the next day.

We got up early the next morning, ate breakfast at the Corner Café, then checked out. We took the advice of the concierge — he told us it would cost less to take a cab to O’Hare than to pay for two tickets on the Shuttle and he was right. The cab was $5 less than the two Shuttle tickets had been, and were were not crowded into a van that had to make stops at several hotels along the way.

We arrived at O’Hare, checked in, and then spent a few hours at the Admirals Club before boarding our 4:00 flight to Austin.

We were both upgraded to first for the flight on an MD-80. We would not arrive in Austin until after 6 p.m., so I assumed we would get a meal in first class, but I was wrong. We were served beverages, heated nuts, and a cookie. It was not the meal I hoed for, but was certainly better than anything we woudl have gotten in Coach.

We landed in Austin on time and as we got off the plane I left one of my bags in the overhead bin and did not realize this until after I had left the terminal. Fortunately, great service from the AA staff in Austin helped me to get my bag back promptly.

All in all, our trip to Chicago was a lot of fun. We agreed that our time in Chicago was much more pleasant and less hectic than our trip to Rome the year before.  We’d be very happy to visit Chicago again, as long as it is not in the middle of winter. If you are looking for a city that is fun, easy to get to, lots of public transportation, and many fabulous sites, take a look at Chicago. You’ll be glad you did!