While on my solo trip through the heart of the Midwest, I couldn’t resist the magnetic pull of Chicago. With 48 hours to spend, I embarked on a solo escapade to the Windy City. Join me on a delightful journey, discovering over 15 captivating things to do in Chicago and crafting your perfect day itinerary.
Traveling to Chicago: Gateway to the Midwest
Chicago O’Hare International Airport (ORD) stands as the bustling gateway to the city, connecting to numerous domestic and international flights. For those craving a scenic entrance, consider driving into the city or catching a train to soak in the Midwest landscapes.
Getting Around in Chicago: Effortless City Exploration
Upon arrival, navigate the city with ease. Chicago’s well-connected public transportation, including buses and the iconic “L” train, ensures a seamless journey through its diverse neighborhoods.
Grab a Chicago Transit Authority (CTA) pass for unlimited rides and download the Transit app for convenient ticketing. You can also take shared rides such as Uber, Lyft, or taxis they are all available in Chicago.
Where to Stay During Your Perfect 3 Day Chicago Trip
For a solo explorer seeking both comfort and proximity to the city’s heartbeat, I found solace at Intercontinental Magnificient Mile.
Nestled in the heart of the city, this urban oasis offers a perfect blend of modern design and warm hospitality. With Intercontinental Magnificient Mile’s central location, I felt the pulse of Chicago right at my doorstep.
Staying at Magnificent Mile can be expensive however can be worth it. Magnificent Mile is located close to many Chicago tourist attractions such as The Art Institute of Chicago, 360 Chicago, Museum of Ice Cream, Museum of Contemporary Art Chicago, and many more. Most of these places are within walking distance.
Places to Eat In Chicago
Diverse Culinary Options in Chicago:
- Chicago offers a plethora of dining choices, catering to various preferences and cravings, ranging from international cuisines to casual and fine dining.
- Whether you’re a fan of trying new restaurants or prefer non-chain establishments, the city has a vibrant food scene that caters to all tastes.
- From the E. Illinois St. and Michigan Ave area to Portage Park, Chicago boasts a variety of dining experiences, including brunch at Egg Harbor Cafe and authentic deep-dish pizza at Lou Malnati’s.
Iconic Chicago Eats:
- Indulge in iconic Chicago eats at Portillos, known for Chicago-style hot dogs and Italian beef sandwiches, as well as the famous chocolate cake shake.
- For a unique burger experience, visit the historic Billy Goat Tavern and savor their renowned “cheezborger.”
- Immerse yourself in the blues and jazz scene while enjoying BBQ at Kingston Mines, providing a distinct Chicago dining experience.
Fine Dining and Steakhouses:
- Explore fine dining options in Chicago, with steakhouses like Gibsons Bar & Steakhouse and Michael Jordan Steakhouse offering a memorable but relatively pricey experience.
- Whether you’re in the mood for a steak dinner or looking to savor Polish and Mexican cuisines in Portage Park, Chicago’s culinary landscape caters to diverse tastes.
- The city’s culinary richness extends beyond its renowned deep-dish pizza, ensuring a delightful and varied dining adventure for every palate.
Things to do during your 3 day Chicago trip
Millennium Park: Art and Greenery
Begin your Chicago odyssey at Millennium Park, where art seamlessly blends with nature. Marvel at the iconic Cloud Gate sculpture, affectionately known as “The Bean,” and enjoy a leisurely stroll through the lush gardens. Unfortunately, the Bean, Chicago’s popular photo spot is temporarily closed to the public from August 15, 2023, until Spring 2024. However, you can still enjoy Millennium Park and its surroundings.
The Art Institute of Chicago: A Masterpiece Haven
Immerse yourself in artistic brilliance at The Art Institute of Chicago. From timeless classics to contemporary marvels, the museum promises a captivating journey through the world of art. This is one of the oldest and largest museums in the world.
It’s really big, and I was not able to finish the entire museum due to time. If you like art and a little bit of history this is your place. There is an entrance fee which is $32 for adults, $26 for seniors, students (college/university), and Teens aged 14-17 and free for children aged 13 and under. Per the website, for Chicago residents with valid IDs and addresses, the entrance fee is $14. Check more about tickets, pricing, and specials here.
An architecture boat tour
- Architectural Boat Tours:
- Wendella Boats offers an informative and entertaining perspective on Chicago’s history and design.
- Ideal for architecture enthusiasts and those seeking a unique experience in the Windy City.
- Booking Tips:
- Advance booking is recommended, especially during peak tourist seasons, to secure preferred time slots.
- Wendella Boat Tours provides options like the 90-minute Lake & River tour for $42 and the 45-minute Chicago River Tour for $27.
- Enhance Your Experience:
- Enjoy the tour with the convenience of a boat bar, offering drinks for purchase during the journey.
- Explore more about tour options and prices here.
Chicago Crime Tours
- Discover Chicago’s Dark History:
- Crime tours unveil the city’s notorious past, exploring gangsters, speakeasies, and organized crime, including the stories of Al Capone and John Dillinger.
- Chicago Crime Tours, priced at $41, provides an immersive experience on a tour bus, stopping at significant locations and offering engaging storytelling.
- Tour Highlights:
- Visit former speakeasies, crime scenes, and notorious hangouts with interactive elements, including the spot where John Dillinger was shot.
- Consider Before Booking:
- Approach crime tours with a historical perspective, avoiding the glorification of crimes.
- Delve into Chicago’s transformation and the impact of organized crime during different eras, but consider your interests and comfort level before booking. For details, check here.
360 Chicago The Tilt
- Iconic 360 Chicago Observation Deck:
- Formerly known as the John Hancock Observatory, this attraction on the 94th floor offers breathtaking 360-degree panoramic views of Chicago.
- Marvel at the city skyline, Lake Michigan, and beyond while enjoying drinks at the Cloud Bar.
- TILT Experience:
- Experience the thrill of TILT, a glass-enclosed platform that tilts outward over 1000 feet, perfect for the adventurous.
- Different ticket packages are available, such as Sip, Tilt & View, Sip & View, Tilt & View, and General Admission, starting at various price points for adults and youths.
- Ticket Packages and Pricing:
- Explore options like Sip, Tilt & View starting at $52 for adults, Sip & View at $43, Tilt & View at $39 for adults, and General Admission at $30.
- Prices vary based on factors like the day of the week. For more details and reservations, check here.
The Chicago Fed Money Museum
- Engaging Money Museum Experience:
- Located within the Federal Reserve Bank of Chicago, the Money Museum offers an educational journey into money, economics, and the functions of the Federal Reserve.
- Explore interactive exhibits, rare historic currency, and presentations, including the famous $1 million cube of cash.
- Free and Family-Friendly:
- Admission to the Money Museum is free, making it a family-friendly attraction in the heart of the downtown Chicago financial district.
- Check the official website for hours of operation and any special events, ensuring an informative visit for both individuals and educational groups.
Plan Your Visit
- Located within the Federal Reserve Bank of Chicago, it’s a valuable stop for those curious about monetary systems and their functions.
- For more information and updates, visit The Fed Museum Chicago.
The Magnificent Mile
- The Magnificent Mile: Chicago’s Premier District:
- Renowned shopping and entertainment hub in the heart of Chicago, attracting both tourists and locals.
- Famous for upscale shopping, featuring high-end department stores, luxury boutiques, flagship stores, and specialty shops.
- Offers diverse dining options, from fine dining to casual cafes and food trucks, creating a vibrant and accessible experience.
- Shopping Extravaganza:
- Explore designer fashion, jewelry, electronics, and home goods, making The Magnificent Mile a go-to destination for a variety of shopping needs.
- Easy Access:
- Easily accessible by public transportation, with nearby bus stops, train stations, and a well-connected network of roads, ensuring a convenient visit.
Weather and Time Constraints during your perfect 3 day Chicago trip
- Rain affected plans for outdoor attractions like Navy Pier, impacting the overall enjoyment.
- Advisable to book tickets early for popular sites like Willis Tower and the Museum of Ice Cream due to high demand.
- Crowds in Millennium Park led to skipping The Bean, but exploring the Magnificent Mile and visiting stores and restaurants provided alternative experiences.
Timely Visits Matter
- Importance of securing time slots in advance, especially for crowded attractions like Willis Tower and popular spots like The largest Starbucks.
- Early visits to busy places can enhance the experience before larger crowds gather.
Adapting to Conditions
- Flexibility in plans due to weather conditions, such as avoiding outdoor locations during rain.
- Despite challenges, exploring alternative attractions and visiting popular sites strategically can still make the trip enjoyable.
One thing I realized on this trip to Chicago I need to make arrangements in advance and I also need more time because there are too many things to do and too many people are visiting Chicago.
Not every place you can go and show up and get tickets, some can be sold out or not match your schedule/availability. Also, I feel like summer will be a good time to go visit, you will be able to enjoy a lot of activities especially the tours most of which are outdoors.
Overall all the places I visited its what I expected, I have been in some cities where what I see on the websites, and social media is different from what I encountered. Chicago is the place I can see myself going back to again because it has a lot to offer but it has to be summertime.
If you’ve explored Chicago before, we’d love to hear about your favorite spots and stories in the comments below. Have questions or need more tips for your upcoming trip? Don’t hesitate to ask. The best journeys often begin with shared experiences and helpful advice, so let’s keep the conversation going!”
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