Chicago is an absolutely amazing city, known for its striking skyline, world-class food, and deep cultural history. It’s a city that perfectly balances its bustling urban energy with beautiful parks and the stunning backdrop of Lake Michigan. Even with only 3 days in Chicago, you can do and see so much—and there are endless festivals, museums, shops, restaurants, parks, and cafes to explore.
Historically, Chicago has played a huge role in shaping the U.S. Known as “The Windy City,” it was founded in 1837 and grew rapidly due to its prime location as a transportation hub between the East and West. Despite the Great Chicago Fire of 1871, which destroyed much of the city, Chicago rose from the ashes to become one of the world’s great architectural cities.
I’ve been to Chicago several times, so let me introduce you to some of the must-see activities and sights in this 3 days in Chicago travel guide and itinerary!
Where to Stay in Chicago
If there’s one place I’ll keep coming back to again and again, it’s the Langham Chicago. Our stay at the Langham was nothing short of spectacular. The views alone are worth the stay—absolutely stunning! Whether you’re looking out over the river or the city skyline, the scenery is breathtaking from every angle. If you’re interested in getting this same view, book the Lake View Suite.
The service is impeccable and truly sets The Langham apart. Every staff member I interacted with went above and beyond to ensure my comfort and satisfaction. I also have to rave about the Langham’s club—the rotating food offerings were phenomenal. We did breakfast in the sky, afternoon tea, and kept coming back for great snacks and views into the night. I can confidently say this hotel defines luxury in Chicago.
If you’re looking for something a little bit more on a budget, here are some other suggestions for staying in Chicago.
Mid-Range Hotels in Chicago
- The Allegro Royal Sonesta Hotel: A stylish and historic hotel located in Chicago’s Theater District. It offers modern amenities with an art-deco vibe, making it a great choice for those who want comfort and proximity to downtown attractions.
- Cambria Hotel Chicago Loop – Theatre District: This trendy hotel offers spacious rooms and is just steps from iconic Chicago landmarks. It’s perfect for visitors looking for a chic stay in the heart of the city without breaking the bank.
Budget Hotels in Chicago
- Chicago Getaway Hostel: Located in the vibrant Lincoln Park neighborhood, this budget-friendly option offers private rooms and shared dorms. It’s ideal for travelers who want a comfortable, social atmosphere close to popular sites and parks.
- Freehand Chicago: A stylish, budget hotel/hostel hybrid in the River North area. With its artsy vibe, communal spaces, and great location, it’s a perfect option for budget-conscious travelers looking to stay near the city’s nightlife and cultural spots.
How to Get Around Chicago
When I visit Chicago, I always rely on the Chicago Transit Authority (CTA) to get around. It’s the most convenient way to explore the city, especially if you’re sticking to the downtown area. I recommend getting a Ventra Pass or multi-day transit card, which you can use on both trains and buses.
The L trains or Chicago Loop trains are super easy to navigate and connect most of the downtown area, making it really simple to get from one spot to another. If you’re planning to visit neighborhoods outside the city center, the bus system is a great option and gets you to those slightly further spots with ease.
While the CTA covers most of the city, supplement with Uber or Lyft for trips that are a bit out of the way. I don’t recommend driving in downtown Chicago because parking can be tough to find, not to mention expensive. Since this itinerary is centered around downtown, you’ll have no trouble sticking to public transportation and ride-sharing apps without needing a car.
With logistics out of the way, let’s dive into the actual itinerary for a wonderful 3 days in Chicago for first-time visitors!
Day 1: Exploring the Iconic Sights
Morning
Start your 3 days in Chicago by getting familiar with the city’s lively and bustling downtown area. Wake up leisurely and have a slow morning—my favorite!
Walk along the iconic Chicago Riverwalk, a beautiful pedestrian path that lines the Chicago River. Along the way, you’ll find plenty of photo opportunities, so take your time snapping pictures of the city’s towering architecture and bridges. A lot of these buildings and bridges are historic and an iconic part of the Chicago skyline!
Afternoon
For a relaxing midday break, indulge in afternoon tea at the Langham. The parlor here is so beautiful and even features a live harpist. Savor delicate finger sandwiches, scones, and pastries in one of the most luxurious settings in the city. I will say that the seasonal afternoon tea at the Langham is definitely not your typical afternoon tea—enjoy all the surprises along the way!
Next, head to one of Chicago’s most popular attractions: the Chicago Skydeck. Located at the Willis Tower, it’s the highest observatory in the city. While the views are great, the main draw here is the Ledge—a glass skybox that extends out from the building, giving you the thrilling experience of standing 1,353 feet above the city with a clear view below your feet.
Each group gets only about 90 seconds on the Ledge, but if you’re keen to take more photos, you can hop back in line for another turn. It gets extremely busy here, especially on the weekends, so I recommend allocating plenty of time here!
Evening
In the evening, take in Chicago’s world-renowned architecture from the water with a Chicago river cruise. I recommend booking a timeslot for 6:30 p.m. to get stunning sunset views over the skyline (though of course the time of sunset will change throughout the year—I took it in August). The Chicago Architecture Foundation Center River Cruise, operated by Chicago’s First Lady, is one of the best ways to learn about the city’s iconic buildings and their history.
Seriously, if you’re into architecture or urbanism, this cruise is not to be missed. The guides are incredibly knowledgeable about Chicago’s history and how human geography and nature have shaped the urban landscape. And even if you’re not into those things, the views from the boat are just fantastic—so don’t skip it! I rate this one of the absolute best experiences to include in your 3 days in Chicago.
Cap off your day with dinner at Au Cheval, an upscale burger restaurant that’s gained iconic status in Chicago. Known for serving one of the best burgers in the country, it’s well worth the wait—just be prepared for a long one, especially on weekends. We once waited two hours during a holiday weekend! Make sure to get the burger with extra bacon and a sunny-side up egg.
Day 2: Parks, Views, and Chicago-Style Pizza
Morning
On the second day of your 3 days in Chicago, start your morning with a walk along the Lakefront Trail. This scenic path runs along Lake Michigan and offers beautiful views of both the water and the city skyline. It’s a perfect way to start your day while soaking up some fresh air. I can never believe that the shore is actually a lake—it’s so vast, it looks just like the ocean!
After working up an appetite, head to Venteux for brunch. With its giant windows and lush green surroundings, this chic French restaurant offers a relaxed vibe and delicious food. The ambiance and natural light make it a top brunch stop during your 3 days in Chicago.
I highly recommend getting the crab eggs benedict—thank me later! Venteux is also famous for their oysters and they were delicious, even for someone who doesn’t really like oysters (sorry).
Afternoon
Next, take a stroll to the Nature Boardwalk at Lincoln Park Zoo. The boardwalk here is surrounded by lush greenery, making it a great spot to unwind! The fascinating honeycomb-shaped structure in the middle of the park is one of my favorite photo spots in all of Chicago—there are just so many cool angles to take from it.
Next, head to 360 Chicago, the city’s second-highest observatory, located in the John Hancock building. I know it might seem redundant to have two observatories in one Chicago itinerary, but it’s a must-see during your 3 days in Chicago. Don’t miss the TILT experience, where you lean 30 degrees over the edge of the building for a thrilling view. It’s actually a bit scary even if you aren’t afraid of heights, but I still loved it and would definitely do it again!
360 Chicago also offers a Cloud Bar as part of their observatory. I recommend staying to have a drink during golden hour or sunset! The colors of the sky are just unforgettable and this was one of my favorite memories from our 3 days in Chicago.
Evening
Your 3 days in Chicago wouldn’t be complete without trying some authentic Chicago deep-dish pizza! There’s always a huge debate about which is the better spot: Lou Malnati’s or Giordano’s. Locals seems to prefer Lou Malnati’s, so it’s my go-to as well. There are several Lou Malnati’s locations across Chicago, so if you want to avoid wait times, pick one that’s a little further from central downtown.
End your day at Buckingham Fountain. The nightly light and water show is the perfect way to wrap up day two of your 3 days in Chicago, offering a peaceful and beautiful scene in the park!
Day 3: Cafes, Art, and Rooftop Views
Morning
Your final day of exploring 3 days in Chicago is all about relaxation and art. Spend the morning cafe hopping or mural hunting in some of the city’s trendiest neighborhoods. Chicago has a busy street art scene, and you have quite the pick of murals—though it’s easier to get to most of them if you have a car.
For lunch, visit the stunning 3 Arts Club Cafe. Housed in the Restoration Hardware building, this beautiful space is filled with greenery, chandeliers, and marble details. It’s one of the most picturesque dining experiences in the city and a great addition to your 3 days in Chicago.
☕ Read more: The Most Beautiful Restaurants & Cafes in NYC
Afternoon
After lunch, head to Millennium Park, home to the famous Cloud Gate, affectionately known as “The Bean.” Created by British-Indian and widely disliked artist Anish Kapoor, it was unveiled in 2004 and has since become a symbol of the city. The sculpture is made from 168 stainless steel plates that are seamlessly welded together, giving it a smooth, mirror-like surface.
The Bean is one of the most recognizable landmarks in Chicago and a must-see during your visit. Don’t forget to explore the park’s green spaces, art installations, and the peaceful Lurie Garden. This park is a highlight of any 3 days in Chicago itinerary.
Another fun part of the park is the Crown Fountain, a unique and interactive public art installation. Designed by Spanish artist Jaume Plensa and also completed in 2004, the Crown Fountain consists of two 50-foot tall glass block towers at each end of a shallow reflecting pool. The fountain’s unique feature is the LED video displays that project the faces of over 1,000 Chicago residents “spitting” water into the pool below.
Evening
As the sun sets, head to the LondonHouse Chicago rooftop for panoramic views of the city. Half the rooftop is reserved seating only, so I recommend making a reservation in advance. While cameras aren’t allowed, you’ll enjoy golden views over the Chicago River with the light reflecting off the multitude of glassy buildings. If you have the budget for it, the food at LondonHouse is also excellent (though admittedly very expensive). If you can only get one item, I have to recommend the seared scallops—I had two plates!
If you’re still hungry and willing to drive a bit, I recommend Al-Bawadi Grill. Chicago has one of the largest Palestinian communities in the United States and this restaurant is one of the most famous and authentic in the whole country! Be sure to try the knafeh for dessert—it’s just incredible, and a fantastic way to conclude your 3 days in Chicago.
Chicago is truly a wonderful city, offering so much for first-time visitors to explore. Honestly, with its great mix between nature and city atmosphere, you’ll quickly realize that 3 days in Chicago is just enough to get a taste of everything this dynamic destination has to offer. After just scratching the surface, come back for a deeper dive next time!
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