This is my personal wrap up of the best things to do in Chicago. There’s so much to experience in this fascinating city by the lake. I still have a lot I want to see even after living here for over 30 years. Chicago is always evolving so it’s impossible to get bored.
Chicago – My kind of town
Chicago’s nickname is the Windy City. The nickname dates back to the late 1870s. Then editor Charles A. Dan of the newspaper the “New York Sun”, wrote that “Chicago was windy because of its politicians being full of hot air.” If you were to ask someone from Chicago, if that reputation has changed, the answer would be no. Although known for it strong political ideology, Chicago is also known for its beautiful skyline, its diverse neighborhoods, amazing food scene and its architecture.
Where to stay while in Chicago
If you really want to get to know this fine city, up-close and personal, I suggest staying in the downtown Chicago area, within walking distance of a number of tours, attractions, and Lake Michigan. Click here to explore hotel rates in downtown Chicago.
The Best Things to Do in Chicago
Purchase a Go Chicago Card
- I recommend the all-inclusive Go Chicago Card pass for $135. The all-inclusive pass allows admission to 26 tours and attractions without having to stand in long ticket lines at each attraction/tour. Download the Go Card App for easy access to your Go Chicago Pass.
Chicago Architecture River Tour
- This is an awesome way to view the city. I chose to use my Go Chicago Card and jump aboard the Shoreline Sightseeing “Chicago Architecture River Tour”. It is a 1-hour tour of the Chicago River and the architectural landmarks that are along the river. There are 2 departure points – Navy Pier or Michigan Avenue Riverwalk (401 N Michigan Ave Plaza – look for the signs).
Recommendation: board at the Michigan Avenue location. There’s usually a long wait at the Navy Pier location.
Where to stay: InterContinental Hotel Chicago, 505 North Michigan Ave – Click here for rates.
BigBus Tour (Double Decker)
- I absolutely love double-decker tours. It is usually my first tour choice when visiting a city. It’s a great way to get a lay of the city and provides transportation to most tours and attraction.
I like to catch the BigBus Tour on Columbus Drive, right in front of the Sheraton Chicago. There’s seating while you wait for your BigBus and a great place to people watch – my favorite pass time. I flashed my Go Chicago Card and upgraded to a second day for $15.
Big Bus Chicago is a great way to get a feel for the city and provides transportation to most of tours and attraction on your two-day quest. You can hop on and hop off to explore the city’s attractions such as the Field Museum, Millennium Park, Navy Pier and much more. The panoramic top-deck view is perfect for taking amazing photos of the city.
Recommendation: If you decide to sit up top, enjoy the breeze from Lake Michigan. Bring a jacket, hat, and shades just in case.
- Completed in 1916, Navy Pier has been repurposed several times as a jail for draft dodgers, a training center for the U.S.Navy, and facilities for the University of Illinois at Chicago. Navy Pier has now evolved into a major tourist attraction that includes a children’s museum, a Ferris wheel, a concert venue and tons of places to eat. One day I will get the nerve to try the Ferris wheel. Well, maybe I will.
Recommendation: catch a movie at the IMAX theater or a free performance at Polk Brothers Park. Check out Navy Pier’s Calendar of Events.
Museum of Contemporary Arts (MCA)
- I use my Go Chicago Card (membership has its benefits) for admission into the MCA. Founded in 1957, this museum features provocative art and exhibitions meant to inspire the artist in all of us.
Recommendation: Before your visit, the MCA go online to get a heads up about the ever-changing exhibitions.
Poster Outside of MCA
The Robie House
- The Robie House is located at 5757 S. Woodlawn in the neighborhood of Hyde Park. The architect Frank Lloyd Wright designed this prairie-style home that has become an icon in the architecture world for a businessman by the name of Frederick C. Robie. It was completed in 1910. Click here for tour times.
Recommendation: After the tour, stop at Plein Air Cafe (right next door to Robie House) for a refreshing cup of tea.
Museum of Science and Industry
- The Museum of Science and Industry is located at 5700 S Lake Shore Drive, is the last remaining building of the 1893 World Columbian Exposition. It is now home to the largest science museum in the western hemisphere. What’s great about this museum is there’s something of interest for people of all ages.
Recommendation: Check out the Coal Mine and U-505 submarine exhibit. After you finish up at the Museum of Science and Industry, Uber it to Medici on 57th for pizza – 327 E. 57th St.
Willis Tower (233 S Wacker)
- This tower will always be known to me and most Chicagoans as the Sears Tower. The former Sears Tower is now the Willis Tower; so named since 2009, for a global insurance brokerage company.
On a clear day in, you can see 4 states – Illinois, Michigan, Wisconsin, and Indiana. It is the 12th tallest building in the world and is home to the highest public viewing area in the United States. The Skydeck located on the 103rd floor of the Willis Tower features the LEDGE. It is four glass boxes on the western side of the Skydeck for observing the street underfoot.
Recommendation: You will have a long wait for the elevator ride to up to the Skydeck. Get your belly full of breakfast at the Original Pancake House (22 E Bellevue Pl) before tackling this attraction. There’s no vending machine or snack area once you get to the Skydeck. You will be on your feet the whole time so wear comfortable shoes. The only seating is a metal bench near the bathroom.
Art Institute of Chicago (111 S Michigan Ave)
- The Art Institute of Chicago was founded as both a museum and a school of fine arts in 1871. However, the Art Institute didn’t find it’s present home until 1893 when the building, flanked by 2 lions, was built for the World’s Columbian Exposition. The Art Institute of Chicago houses a permanent collection of more than 300,000 paintings, exhibits, and artifacts. There is something for the art lover in all of us at this museum. Expect to spend at least a couple hours in this large museum.
- Recommendation: if you get hungry stop by the Terzo Piano for a light lunch and glass of wine.
Field Museum (1400 S Lake Shore Drive)
- Founded in 1893 as part of the World’s Columbian Exposition, the Field Museum is home to world-class scientific researchers, extraordinary exhibits and Sue, the T-Rex.
Recommendation: If you’re not all museum-ed out by now, check out Shedd Aquarium and the Adler Planetarium. All three museums (and Soldier’s Field – Home of the Chicago Bears) are part of the Museum Campus (1400-1562 S. Lake Shore Drive).
The Hancock Building
- This 100 story skyscraper is the 4th largest building in Chicago. The 360 Observation Deck at the Hancock building has the TILT attraction which is a series of floor to ceiling windows that slowly tilt outside the building to 30 degrees. The charge for that is $7.00. If you pre-purchase your tickets online (which I recommend) the cost is $6.30. On my visit to the Hancock Building, I decided to skip the TILT because of the long lines. Instead, I grabbed an alcoholic beverage and found a seat to one of the best views Chicago has to offer.
Recommendation: If you are looking for more of a chilled-out experience the observation deck has wide-wooden bleacher-like seating. Perfect for taking in the breathtaking views of Chicago.