Chicago is an architectural delight, with a mix of old and new buildings. They all have interesting histories and are within walking distance to take in the views and the cuisine. A river cruise is a must do and there are a lot of options to choose from. Chicago is also a place to visit if you like food.
Friday
We flew into O’Hare airport and used the transit train service between the Airport and downtown which took around 45 minutes. However, if you fly into Midway, the train ride is a bit shorter at 25 minutes.
We stayed at the Blackstone Hotel at 636 South Michigan Avenue which is a short 4 minute walk from the Harrison stop on the Red Line. However, from O’Hare, it’s probably better to stay on the Blue Line to LaSalle and have a 10 minute walk. The hotel is part of the Autograph Collection of hotels which we love to stay in as they always have a unique, boutique feel. I always enjoy going floor to floor to see all the art work.
The hotel opened its doors in 1910 and was once the tallest building in Chicago and has been recently renovated to combine its history with modern furnishings. The location is within walking distance for all of downtown Chicago. For example, it’s opposite Grant Park that fronts the lake and just 10 minutes from the Art Institute of Chicago if the art in the hotel gallery isn’t sufficient to fill your artistic needs. We arrived fairly late so we headed to the downstairs bar which serves authentic Catelan tapas from Mercat a la Planxa, the hotel restaurant.
Saturday
Millennium Park and the Magnificent Mile
We walked along the Lakefront trail from Grant Park to see the views of the Chicago skyline and visit the Millennium Park – Cloud Gate (a.k.a. the Bean). There are usually crowds taking photos of the Bean, but it’s worth the wait to get the reflections in the photo. We saw some of the free workout sessions performed in the lawn in front of the Jay Pritzker Pavilion. Close by is the Crown Fountain that’s fascinating to wait and see the water coming out of someone’s mouth. The people are videotaped from the crowd.
We were fascinated by the architectural backdrop of the city. There is such a variety of the old and new and no building looks the same. We then headed to the Magnificent Mile for some window shopping and architecture gawking, including the historic Water Tower, one of the few buildings to survive the Great Chicago Fire of 1871. Just by the river we marveled at the gothic Tribune Tower, home to the Chicago Tribune. The façade has over 120 stone fragments that reporters collected from around the world.
Chicago Riverwalk
We then strolled along the Chicago Riverwalk where we could preview more of the city’s architecture. This helped align us in the city when we were on the architecture boat tour. For lunch we stopped at the Sheraton Grand Chicago to get a snack at their cafe and sit in the airconditioned lobby watching the crowd walk past.
The 1.25 mile long pedestrian only walkway gives a riverside perspective of the city. You can watch the tour boats, kayaks and pleasure boats on the river. There’s also the fasciation of people watching at the riverside cafes, meeting places and unexpected fountains. Each bridge has different characteristics and a birds eye view of the traffic on the water.
At night several of the buildings are lit up and you can see the Art on the Mart, a public art installation that projects images on the side of Merchandise Mart every evening.
Chicago Architecture River Cruise
The riverwalk took us in the right direction to reach Navy Pier where you can view the Ferris Wheel and other attractions. This is the place where we met up with our pre-booked Chicago Architecture river cruise that provided background on Chicago’s famous skyscrapers like the Willis Tower, the Wrigley Building, the Leo Burnett Building, the Fulton House and Tribune Tower. This is one of the highlights of the weekend so get a seat near the front to see all the sights.
We walked back to the hotel via the Lakefront Trail and Grant Park and the Buckingham fountain light and show. Then another trip to the Art Institute of Chicago to see the Miniature Gallery. We had joined the gallery to get a discount on admission and I was able to fit in a quick look around the Manet exhibit. It’s so fascinating to see the brush or pen work of the masters.
Dinner that night was at the downstairs bar for some more delicious tapas and to watch the Wimbledon Tennis on the television.
Sunday
Art Institute and Riding the Loop
The whole day can be happily spent at the Art Institute of Chicago seeing the permanent installations or exhibits. There are so many marvels including the history of photography, a fascinating paperweight collection and viewing the Marc Chagall stained glass window.
TIP: A benefit of joining the Art Institute was access to the members lounge for a much needed cup of tea. Later we went to the café for lunch. I remember my spritzer had some lovely flowers as well to make it feel special!
Afterwards travel the Loop – the elevated train tracks for a loop around the downtown area. This is a great alternative view of the city than walking. If there’s time, you could take other lines to see different Chicago Neighbourhoods. Or do a 3 hour walking tour of the Loop for some deep dish pizza tasting and Chicago stories.
TIP: We had walked to get some deep dish pizza but the line was too long for our patience. So we found Au Bon Pain, a quiet sandwich place, and ate in peace on the patio.
Then it is back to the hotel to pick up your luggage and return home.
Other things to do in Chicago
Along the Lakeside walk you could stop at the American Writers Museum with a collection of five centuries of writing. Or at the other end of the Lakeside walk there are several Museums such as the Field Museum and Adler Planetarium.
TIP: This is a great place to take sunset photos of the Chicago Skyline. Or take one of the boat tours out on the lake to get views of the city and Navy Pier from a different perspective.
Once you have seen all the buildings on the architecture cruise, you could visit the Willis Tower, 360 CHICAGO or Skydeck Chicago for a good overview of the city’s layout.
There’s also the 606 a nearly 3 mile stretch of an abandoned elevated rail line that has been transformed into a pedestrian path that connects Logan Square, Humboldt Park, Bucktown and Wicker Park. Take transit via the CTA Blue Line.
Or head to Goose Island Beer Company for an hour long tour and tastings. Close by is OZ Park where you can see statues of the characters from the Wizard of Oz.
Best Chicago Photo Spots
- Millennium Park and Cloud Gate - best time to photograph is sunrise, especially to avoid the crowds.
- Jay Pritzker Pavilion - designed by Frank Gehry it has sheets and rods of steel framing the stage.
- Cindy’s Bar - located at the top of the Chicago Athletic Association Hotel with great Millennium Park
- Milton Lee Olive Park - a quiet park just north of Navy Pier with a great view of the Chicago Skyline
- Willis Tower Skydeck - not only can you see 4 states on a clear day, there is also a glass floor with views of the street below.
Chicago Inspirations
- The Blues Brothers
- Chicago
- The Trial of the Chicago 7
- Bad, Bad Leroy Brown • Jim Croce
- Chicago Blues • Oscar Peterson
- Divergent • Veronica Roth
- The Time Traveler's Wife • Audrey Niffenegger
- Humboldt’s Gift • Saul Bellow
- The Devil in the White City • Erik Larson
- Indemnity Only • Sara Paretsky
When to visit Chicago
We were there at the end of August and enjoyed the warm weather.
In Fall the foliage in Chicago is amazing and the colours peak around the end of October. The Open House Chicago gives you entry to the inside of some of the wonderful buildings that otherwise you can only see from the outside.
St. Patricks Day – the weekend before St. Patrick’s Day in March is a big time to visit the city, including when they dye the Chicago river green. It’s busy and cool at about 45’F at the parades on Saturday and Sunday.
Events of Note:
May / June – Chicago Blues Festival
June / July – Taste of Chicago
July – Lollapalooza Rock Festival
August – Chicago Air and Water Show
August / September – Chicago Jazz Festival
September – World Music Festival
November / December – Magnificent Mile Holiday Lights Festival
