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This is my personal wrap up of the perfect 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.
Click here to book your hotel in downtown Chicago.
Chicago’s nickname, Windy City, 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.” The city is still very political. But we also know how to have fun.
A visit to Chicago is a visit to a city known for its beautiful skyline that frames Lake Michigan, its sports teams and its relationship to hot dogs and pizza.
Looking for a guide to Las Vegas? Click here.
There are a lot of things to do in Chicago for the older woman solo traveler. Chicago is so huge and diverse that it’s impossible to capture all of it in one post or travel guide.
Chicago Solo Travel Guide
Yes, parts of Chicago can be dangerous. But don’t most cities (both U.S. and abroad) have parts that are considered not safe. But with a little street-savvy and awareness of how you’re presenting yourself, you will be fine.
- Just like any city that you visit, always be aware of your environment.
- Try not to appear touristy.
- If you’re like me and love carrying huge-ass purses, make sure the purse has a shoulder strap that you can wear across your body.
- Never leave your purse on the back of your chair. Especially if you are enjoying a meal at one of Chicago’s many sidewalk cafes/restaurants.
- Do not take shortcuts through alleys. No matter how tempting.
- When going out at night, stick to well-lit sidewalks, main streets, and parks. The lakefront is gorgeous at night. Full of good people with neighborly and friendly mid-western values. Join them and enjoy the amazingly beautiful city that is Chicago. I never get tired of the welcoming energy of my city.
- Enjoy yourself. Stick to downtown and the popular neighborhoods such as (the list is not all-inclusive):
- Hyde Park
- Lincoln Park
- South Loop
- West Loop
- If you do decide to rent a car, parking downtown is very, VERY expensive. Most street parking in Chicago is metered. If you can do without rented wheels, do so. Public transportation is a good cheap option if you’re visiting Chicago on a budget and there’s always Uber and Lyft.
The downtown area and all neighborhoods are heavily patrolled by the City of Chicago Police. Some neighborhoods such as Hyde Park and parts of Lincoln Park are also patrolled by University Police. So like I said…feel free to enjoy yourself but do it safely.
Where to stay: Downtown Chicago
If you really want to get to know this fine city, up-close and personal, I suggest staying in the downtown area. I mean any hotel downtown will just about do. You will be within walking distance of shopping, tours, attractions, and the lakefront.
Going to San Francisco? Not without reading “Perfect Things to Do this Weekend in San Francisco“
The Best Things to Do in Chicago: The best value for your money
- I recommend the all-inclusive Go Chicago Card pass. 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.
Click here to purchase 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”. Use the Go Chicago Card to save money. 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 to book your room.
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. No long lines to hop on at this stop. 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.
Click here to purchase your seat on the BigBus Tour or use your Go Chicago Card for better value.
Recommendation: If you decide to sit up top, enjoy the breeze from Lake Michigan. Bring a jacket, hat, and shades just in case.
Where to stay: Sheraton Grand, 301 E North Water Street – Click here to book your room at the Sheraton.
Big Bus Tour riding along State Street
- 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.
Where to stay: Embassy Suites Chicago Downtown Mag Mile, 511 N Columbus Dr – Click here for current rates.
Museum of Contemporary Arts (MCA)
- Use your 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.
Where to stay: Shop and stay at the Ritz Carlton Chicago, 160 East Pearson St. – It’s location inside the Water Tower Place and near the Magnificent Mile makes it the perfect place to stay if you’re a shopaholic.
Click here to book your stay at the Ritz.
*Little known fact for you Oprah Winfrey fans…She had a condo in this building before she kicked Chicago to the curb for California. I ain’t mad at her though. Chicago winters can be tough.
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 for a businessman by the name of Frederick C. Robie. It was completed in 1910. Mr. Wright’s vision was to build a house that was sleeker with an open space architectural design. The Robie House is the precursor to architectural modernism. Click here for tour times. You can use the Chicago Go Card to gain entry into the Robie House Tour.
Click here to purchase the Go Chicago Card.
Click here to book hotels near the Robie House
Museum of Science and Industry
- In 1933 a building that was the Palace of Fine Arts for the 1893 Columbian Exposition became the Museum of Science and Industry It is located at 5700 S Lake Shore Drive, and not to be missed on your visit to Chicago. It is 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.
What’s great about this museum is there’s something of interest for people of all ages. Many of the exhibits are hands-on with the intention of sparking scientific creativity within.
Exhibits range from subjects such as energy, chemistry, design, transportation, environmental science and so much more!
Recommendation: Use your Go Chicago Card to get in Click here to purchase. MSI is so huge and contains so many exhibits that you should schedule a whole day for visiting all 400,000 square feet of this museum. Don’t rush and take plenty of breaks. What’s so great about MIS is that a lot of exhibits requires sitting….thank God! My favorite is the exhibits in the Transportation Gallery.
Where to stay: Hyatt Place Chicago-South/University Medical Center – 5225 South Harper Avenue.
Click here to book your stay at the Hyatt Place
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.
To experience the Skydeck, click here for the current price.
Recommendation: To save money use your Go Chicago Card to gain entry to the Skydeck. Click here to purchase. You will be on your feet the whole time so wear comfortable shoes. The only seating is a metal bench near the bathroom.
Where to stay: J.W. Marriott Chicago, 151 West Adams. Click here to book your room.
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.
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.
Where to stay: The Palmer House, 17 East Monroe. Click here to book your room.
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). To gain entry and to save money use your Go Chicago Card.
Where to stay: Chicago Hilton and Towers, 720 South Michigan Avenue. Click here to book your room.
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.
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.
Me, chillin’ on the bleacher seating at 360 Observation Deck