Chicago, located in the state of Illinois, is the third largest city in the United States of America. It is also commonly known as the Windy City due to the strong gusts of wind that blow in from Lake Michigan. Chicago is a city that is renowned for its stunning architecture, vibrant culture, and diverse neighborhoods. From the towering skyscrapers of downtown to the picturesque beaches along the lakefront, Chicago is a city that never fails to amaze.
If you’re keen on exploring the wonders of this city, I’d be delighted to provide you with a sample itinerary of the local attractions and experiences that make Chicago such a unique and exciting destination. Additionally, for more comprehensive information, you can peruse my blog, where I offer my personal insights and recommendations on the finest things to see and do while visiting Chicago.
My Sample Itinerary to Start (If you haven’t been to Chicago)
Day 1
- Morning walk at the Chicago River (known as the Riverwalk). Sure, it will be worth trying to get some exercise, like living in Chicago.
- Lunch at the Chicago Pizza, which is a must-try Chicago-style pizza. Another option is to try eating hot dogs with these onions and pickles.
IPT Tips: Chicagoans have their own way of eating hot dogs, and one of their rules is to avoid using ketchup. It is not recommended to put ketchup on your hot dog if you want to eat it like a true Chicagoan.
Following my midday meal, I decided to go for a leisurely stroll to take in some fresh air and explore the renowned North Michigan Avenue, also known as the Magnificent Mile. The street is famous for its upscale shopping outlets and iconic landmarks, making it a popular destination for both tourists and locals alike. As I walked, I couldn’t help but admire the architectural beauty of the surrounding buildings and the vibrant energy of the bustling street. It was the perfect way to spend a relaxing afternoon.
Tips: If you plan to shop at Michigan Avenue, it’s advisable to exercise some extra caution, especially if you are a tourist. This is because the area is known for its high-end brand-name stores, and dressing like a tourist can make you more vulnerable to scams and pickpocketing. Instead, try to blend in with the locals and avoid shopping at the more conspicuous stores. This will help you stay safe while still enjoying all that Michigan Avenue has to offer.
- Millennium Park
Following my lunch, I decided to visit the famous Millennium Park, which had been on my list of must-visit places during my trip to Chicago. While exploring the park, my eyes were immediately drawn to the magnificent Cloud Gate, a bean-like sculpture that had become one of the most recognizable icons of the city. As I stood there admiring its beauty, I couldn’t help but wonder what made the Cloud Gate so special.
Upon further research, I learned that the Cloud Gate, which was established in 2006, was created by the renowned artist Anish Kapoor. The sculpture was designed to symbolize the city of Chicago and its diverse culture and was named after its bean-like shape. The Cloud Gate has since become a popular tourist attraction and has earned widespread acclaim for its unique design and artistic significance.
Spotting something, I put my phone inside my bag. I kept walking, enjoying a lovely, sunny afternoon, and trying to blend in with the locals.
Here are other pictures I took when I visited a favorite place, Millennium Park.
After 1.5 hours in Millennium Park, where am I headed?
- Navy Pier (with a purpose of riding a Seadog for an architectural tour)
When I was in Chicago, I decided to visit Navy Pier, which is a popular tourist attraction that offers a variety of activities and experiences. One of the most popular activities at Navy Pier is the Seadog architectural tour, which takes you on a cruise along the Chicago River and offers stunning views of the city’s skyline. Another popular attraction at Navy Pier is the Centennial Wheel, which is a giant Ferris wheel that offers breathtaking views of Lake Michigan and the city. However, I believe that visiting Navy Pier should have a purpose, such as exploring the city’s architecture or enjoying a fun day out with friends and family. If you simply visit Navy Pier as a tourist, you may miss out on the true essence of the place and its cultural significance.
After joining a mix of travelers and tourists, I was excited to experience what riding on a speeding boat in an open area is like.
During my recent trip to Chicago, I had the pleasure of spending approximately 75 minutes exploring the city’s famous architecture and chatting with both locals and tourists. The experience was truly remarkable as I learned about the history and significance of some of the city’s most iconic buildings. The guides were extremely knowledgeable and passionate about their city, and I found myself engrossed in the conversation. As the tour came to an end, we were treated to a thrilling speedboat ride that left us all exhilarated. The ride was short but unforgettable, and it added a fun and exciting element to an already fantastic experience. Overall, I would highly recommend this tour to anyone looking to explore Chicago’s stunning architecture and learn more about this incredible city.
- Chinatown
As it was already time to head to Chinatown, I decided to gather up my courage and join the group of fellow travelers. We walked along the bustling streets, taking in the vibrant sights and sounds of the lively neighborhood. Amidst the hustle and bustle, I paused to take a picture, capturing a moment of joy and excitement during our visit.
One of the highlights of our trip was discovering the 12 animal zodiacs that adorned South Archon Avenue. Each statue depicted a different animal from the Chinese zodiac, such as the dragon, rat, and tiger. As we strolled along the avenue, we marveled at the intricate details of each statue and learned more about the symbolism behind them. It was a truly unforgettable experience, and I felt grateful to have shared it with such wonderful companions.
Day 2
- Morning at the Willis Tower, known as the Skydeck Observatory.
Built in 1973, it took 3 years with 2,000 construction workers to build the skyscraper. It remains the tallest indoor observatory in the US, 2nd tallest behind One World Trade Center. You can also step onto the 3 layered glass, including the general admission ticket.
Spotted at the Color Factory, taking a photo, it was a “hidden gem.” Hence, the entrance was also a paid fee, costing around $35 to $50, depending on the time and day. I highly recommend spending at least 1 hour in the Color Factory.
IPT (Solo Travel Expert) Tip: When visiting the Skydeck, leave any large bags, weapons, and self-defense items at the hotel. You are subject to random searches at security checkpoints, and carrying larger bags can make you a “tourist.”
Since the general admission ticket is timed, arriving at the ticket counter 15 minutes before your scheduled time is essential. It is highly recommended that you print your ticket before arriving.
Since I arrived early in the day, I decided to choose 8:30 to beat the crowd, and it was on the weekend.
After scanning the ticket, there was a security checkpoint, just like when I caught the flight at the airport. You will place any bags or wallets into the conveyor belt.
As some customers had the photos taken by the Skydeck employees, I highly skipped it. I moved on to learn what Chicago culture looked like in the beginning.
I thought, “I believe that people assume that purchasing additional photo packages can make you a “tourist” rather than “traveler.” Hence, you can ask someone to take your picture, which is cheaper.”
IPT Money Tip: I do not recommend any expedited ticket or additional condiments due to costs, making you a “tourist.” Instead, I highly skip any other fees and photo packages. Instead, have someone take a photo of you, or you can take a picture of yourself.
And yes, there are L’ Train simulators when you pass by.
As I learned what it is like in Chicago, I finally realized that Chicagoans have a unique culture, including performance arts and architectural culture.
I also learned that local cuisine includes Chicago-style pizza and Chicago-style hot dogs.
As I entered the stunning music performance, someone took me, singing on the musical stage.
IPT Tip: The elevator has wait times, so pack your patience.
Elevator: Seeing how each building compared to major landmarks’ height was stunning.
As I boarded the elevator, it zoomed up for about 60 seconds.
IPT Tip: Your ear may pop when ascending and descending on the elevator at Willis Tower. My best advice is to chew gum, eat hard candy, and/or massage your ear tragus.
Here, I arrive 1,353 feet above the ground.
Hint: On a clear day, you will see 4 states: Illinois, Wisconsin, Indiana, and Michigan, with a visibility of 40 to 50 miles.
You must step onto the glass pavement if you want to see the west side. The glass experience is included in the admission ticket.
After a while in the building, I took my time to reflect and recap my overall Chicago trip and…
…there were lines, dreaming of standing on the glass panel.
Since I purchased a general admission ticket, I must wait until it is my turn to stand on a 3-layered .5-inch thick glass.
Fact: The glass you will be standing in is 1,353 feet above, known as the Ledge. It can hold up to 10,000 pounds (5 tons).
Now, it was my turn to step onto the glass. When asked if you have an additional card, I replied I didn’t have one and decided to take my picture.
Since some people were reluctant to step onto the glass, I wasn’t frightened because the glass was “well-protected.”
After about 90 seconds, it was time to reflect on another activity through a writing assignment. And that is the end of the visit.
After viewing, you can visit and relax at the Catalog at Willis Tower. Many restaurants include Sushi San, Starbucks, Do-Rite and Chicken Doughnuts, Sweet Green, etc. Be mindful when selecting a restaurant so you don’t become a tourist.
Chicago Water Tower
Unfortunately, it was raining, making it harder to take pictures while finding landmarks, and I started to blog simultaneously. But it worked when I had to carry my umbrella.
Visiting the shopping mall like the locals, I relaxed and took some time to reflect on how I enjoyed a trip to Chicago and learn about the culture and daily life.
Since I loved shopping, I went there near the tower since it was raining. It was known as the Water Tower Place.
What else to see when you plan a trip to Chicago?
Here is a list of things you can do while on a trip.
- Lincoln Park (duration is 3 to 4 hours), including a visit to Old City.
- Shopping at the Woodfield Mall (Tips: Take the Blue Line Train to O’hare, then take the 606 bus.)
- The Second City comedy show (better to check for upcoming show schedules)
- Visit Chicago Cultural Center (if you love to learn the history)
- Enjoy a visit to the Museum of Contemporary Art Chicago and Adler Planetarium
- Plan a day trip in suburban Chicago (with safety conditions)
- South Side’s Hyde Park, home of the University of Chicago
Or you can plan your itinerary but customize your activities based on your interests and wishes you want to experience and connections.
How will you get around in Chicago?
The best bet to get around Chicago is by public transportation. I researched how much each person is:
- Bus: $2.50 with a free transfer within a 2-hour window
- Subway (The L’): $2.25 with a free transfer within a 2-hour window
- Commuter Rail (Metra): Varies by zone
Chicago Transportation Authority is America’s 2nd most extensive public transportation system, behind the New York City MTA.
IPT Tip: I recommend purchasing an unlimited pass depending on the itinerary you create. If you have a multi-stop, you will save time and money by taking the bus and subway hassle-free.
With a new Ventra Card, you can tap onto any L’ Train Stations and buses within Chicago. The Ventra Card can be purchased at any L’ Train Station.
What should you wear when you are in Chicago?
They mostly wear casual clothes but do dress for the weather. Chicagoans mostly do not dress in brand-name puffy jackets. Try a jacket or coat (during the cold weather instead). Also, I do not recommend dressing in a jersey or sport-themed outfits (unless you travel for sport-related events).
Is Chicago Safe for Solo Travel?
Chicago is a fantastic place to visit if you’re traveling solo. However, it’s important to note that there are certain areas of the city that should be avoided due to safety concerns. As a responsible traveler, it’s essential to do your research and plan ahead to ensure a safe and enjoyable trip.
According to Chicago residents and travel experts, certain neighborhoods located south of Chicago are known for having a high crime rate. Therefore, it’s best to avoid traveling or planning any itineraries that include these areas, even if you’re traveling with a group or a buddy. Safety should always be the top priority, and it’s better to be cautious than to put yourself in a potentially dangerous situation.
If you’re a solo traveler, it’s especially important to be aware of your surroundings and to plan your itinerary carefully. Solo travel experts recommend doing your research ahead of time to find safe and welcoming areas of the city to explore. It’s also a good idea to stay in well-lit areas, avoid walking alone at night, and to keep your valuables secure. With a little bit of planning and common sense, you can have a wonderful solo travel experience in Chicago while staying safe and secure.
Warnings from the Solo Travel Experts: Stay with others at night, even downtown. Do not walk alone. Avoid isolated alleys, deserted areas, or areas with poorer lit. Instead, always stick to well-lit areas where there are lots of people. When possible, have an escort back to the hotel. Try to be back at the hotel/hostel by the sunset.
When is the best time to visit Chicago?
I could say the best time to visit Chicago depends on the circumstances:
- On a budget (including flights and train tickets): November to April
- Best Weather: April to October
- Fewer Crowds: Mid-March to May or Early September to October
- Entertainment (Theater) and Performing Arts: July-August (check the website)
Here are visual pictures of my overall trip to Chicago.
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