Weekend in the Windy City


Chicago Labor Day Weekend 2016

My husband and I spent Labor Day weekend in Chicago. I had lived there during my high school years but had not been back since. We like to take long weekends away and especially like it when we can incorporate some live music into the trip. Chicago was a wonderful choice! The public transportation is great, so we didn’t need to rent a car. There is an amazing variety of things to do. We sampled quite a few over the weekend but are planning a return visit soon.

We flew into Midway and took the train to our hotel. You should be aware that there are several different transit systems in Chicago. The Chicago Transit Authority runs from Midway to the Loop and offers several reasonable fare prices. A one day pass is $10, 3 days cost $20 and you can ride for a week for $28. The trains run continuously from 4 am to 1 am 7 days a week. Our hotel was conveniently located at the stop for State and Lake streets.

We stayed at the Wit, a Hilton hotel. We had a gorgeous 2 rooms suite with a small    kitchenette. We look for rooms with sitting areas when we travel since both my husband and I generally end up doing some work while we are away. It is also an asset when we travel with friends or our now grown children. No need to sit in the hotel lobby or bar when you want to chat. You can get together for a cup of coffee in the morning or an adult beverage at happy hour.

The Wit had a roof top bar with spectacular views as well as a wide variety of wines and spirits (a particularly good selection of bourbons and ryes) and tasty tapas style food.


There was also an excellent restaurant, The State and Lake Chicago Tavern. We got complimentary continental breakfast each day with our stay. We chose to use the credit toward a full breakfast and certainly had plenty to choose from. I had a delicious andouille pimento cheese omelet the first day and then the veggie frittata with manchego cheese the last two days. We also had the house made mini muffins, four different flavors and all were absolutely decadent.

We don’t typically plan activities for the first day of our trips. We like to get the lay of the land and explore the area. We had a great time walking down to the lake and exploring the parks.  We arrived about lunch time and checked Yelp for a good spot to grab a bite. We ended up at the Dearborn at Dearborn and Randolph streets. It was about a 5 minute walk from the hotel and worth every step! I had the French Onion Panini. A decadent sandwich of Gruyere cheese and onions that have been cooked for 9 hours. It is served with a Shiitake Onion broth which keeps it from being too salty. It was so good that I have considered trying to replicate it at home. My husband had a pastrami Reuben  and thought the sauerkraut was some of the best he has ever had. We needed a long walk after lunch to work off all the deliciousness.

Our first night we had dinner reservations at Smith and Wollensky right down State St from our hotel. It is situated on the river in Marina City and has the same architectural style of the restaurant in New York. While the steaks were some of the best we have ever had, my husband was not happy with his baked potato and the meal overall was A LOT heavier than we usually eat. Of course, we did chose to go to a steak house!

Ok, let’s take a break from food. On our second day, we went on an architectural river cruise. The cruise lasts an hour and an half and boards at Michigan Ave and Wacker Dr. It costs $44 per person. I recommend you get reservations and highly recommend taking this cruise. The views of the buildings are outstanding and the docent (all volunteers) are extremely knowledgable and bring their personal style to the tour.


After the river cruise, we walked to the Art Institute of Chicago located on South Michigan Avenue. It was about a 15 – 20 minute walk. We did not purchase tickets in advance but the line moved very quickly. It was $25 for general admission. There is a combination ticket that includes access to the SkyDeck, a 4 foot wide glass deck around the 103 floor of the Willis Tower. You can visit the SkyDeck any day within 7 days of your museum visit. We spent about 3 hours wandering from room to room seeing exhibits ranging from Ancient Chinese art to Modern American Art. I particularly enjoyed the Impressionists. The collection of Van Gogh and Monet were quite large and contained some of their iconic works such as the WaterLilies and Van Gogh’s Self Portrait.

On our third and last day we visited the Museum of Science and Industry located on South Lake Shore Drive. We took a train from the Millennium Park station and got off at the 56th street station just two blocks from the museum. This was not the same CTA service that we took from Midway to the hotel. The train does not run continuously so you need to check the schedule and plan your trip accordingly. The website RTAChicago.com has a trip planner that will help you with times. The trip takes about 40 minutes. I enjoyed seeing other parts of Chicago including Soldier’s Field. The cost was $7.50 per person but there is an $8 weekend pass. The downside for us was that we didn’t watch our time and ended up taking a cab back to the hotel. That was about $30 and VERY SCARY!!! It reminded me of an amusement park ride. I certainly could never drive in Chicago.

Once we arrived at the museum we had many choices of tickets again. The base price is $18 per person with each additional experience costing $12. There are several to choose from: Brick by Brick Lego exhibit, Coal Mine, Great White Shark, National Parks, and Future Energy Chicago.  We chose general admission but the Coal Mine exhibit is on my list for our next trip. That being said, we found plenty to do with the general admission. There is a massive model train that simulate the journey from Chicago to Seattle and an interactive exhibit that explores the science of storms that made my inner geek joyous! Last but not least, we (ok me) were enthralled by Colleen Moore’s FairyTale Castle. Colleen Moore, a famous film star, began construction on the castle in 1928. It has been housed in the museum since 1949. It is filled with wonders from inch square books signed by their authors to miniature statues 2000 years old. Apart from the fairy tale fantasy the construction and engineering of this castle are a wonder.


For our last evening in Chicago, we attended a concert at Ravinia, located in Highland Park and the oldest outdoor music festival in the United States. It was founded in 1904 and presents over 140 events each summer. The events range from classical to current music. We saw OAR and thoroughly enjoyed it. I really wish we had a venue like this in our area.  You can either bring a picnic or purchase food at the park and enjoy the concert from the beautiful treed lawn or get a seat in the pavilion which seats 3400 people. Smoking in not allowed anywhere on the grounds and while beer and wine are plentiful, typically food and drink are not allowed in the pavilion. There are limited terrace seats available at two restaurants on property which provide table service throughout the concert.  The park also has smaller indoor theaters such as the Martin Theatre, the only building remaining from the original park. It seats 850 people and events include chamber music and soloists.

Again, we took the train to Ravinia. Each ticket was $8 and the train went from Ogilvie Station directly to the park gates. This is a special express train that makes no stops on the way out but stops at all locations on the way back. It was so convenient and really nice not to have to worry about parking or driving. Word of warning, there is very limited parking at Ravinia and the police will ticket you for street parking.


Our Labor Day weekend in Chicago was certainly not laborious. We thoroughly enjoyed the public transportation and commented frequently how we wished these services were available in our area. There was an abundance of activities within walking distance of hotel. Chicago has a beautiful riverwalk with plenty of restaurants and bars. City Winery has a location on the Riverwalk. We are watching their schedule for upcoming concerts and planing a return visit. We were located in the theatre district and saw so many shows advertised that we hated to leave. Early September was a great time to visit Chicago. It was warm but not unpleasantly hot. My husband is not a fan of cold weather at ALL so our return trips will need to be scheduled from May to mid October. I am planning already!



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