best places to visit in Chicago in 3 days

Question

with family including 2 kids visiting Chicago for 2 full days and 1 half days. please suggest best places to cover.

In our list

1. Architecture cruise

2. Skydeck tower

3. millennium park

4. navy pier

please suggest must see places and best time of the day to visit them

Answer

It sounds like you have a great list of must-see places for your family’s trip to Chicago! Here’s a suggested itinerary that covers those attractions along with some other notable spots, and the best times to visit them:

Day 1: Architecture Cruise & Millennium Park

Start your first full day with the Architecture River Cruise—this is one of the best ways to see and understand Chicago’s iconic skyline. The cruise is informative and offers great views, especially in the morning when it’s cooler and less crowded. The tours typically last around 75 minutes, and many boats depart from the Chicago Riverwalk, which is easily accessible from most downtown hotels.

Best Time: Morning to mid-morning (before it gets too hot or crowded)

After the cruise, head over to Millennium Park, which is a short walk away. Millennium Park is home to famous landmarks like the Cloud Gate (the Bean), the Crown Fountain, and the Lurie Garden. It’s a great spot for photos and for the kids to play around, especially near the fountains. You can easily spend a couple of hours here.

Best Time: Late morning to early afternoon

After exploring the park, consider visiting the Art Institute of Chicago, which is right across the street from Millennium Park. It's home to some world-class art collections, including the famous American Gothic painting, and has family-friendly exhibits. It’s a great option if you have time and the kids are interested in art.

Day 2: Skydeck & Navy Pier

On your second full day, start with a visit to the Skydeck at Willis Tower (formerly known as the Sears Tower). This is one of the tallest buildings in Chicago, and the views from the 103rd floor are stunning. If you’re feeling adventurous, you can try the Glass Ledge, where you step out onto a glass floor with views straight down to the ground. It’s best to visit early in the day to avoid long lines, especially if you’re visiting on a weekend or during peak tourist season.

Best Time: Early morning (before the crowds build up)

In the afternoon, head over to Navy Pier. This iconic Chicago destination offers plenty of activities for kids and adults alike. You can ride the Ferris wheel for great views, explore the Chicago Children's Museum, or even take a boat ride from the pier. Navy Pier also has great dining options, so you can enjoy a leisurely lunch or dinner with views of Lake Michigan.

Best Time: Afternoon to early evening (before the crowds peak, but after the Skydeck visit)

Day 3: Extra Must-See Attractions & Time for Relaxation

Since you only have a half day on Day 3, I recommend focusing on a few more spots that are easy to get to and enjoyable for the whole family.

The Field Museum: If you have an interest in natural history, the Field Museum is a fantastic place to visit, especially for kids. It’s home to “Sue,” the largest and most complete T. rex skeleton, along with many other exhibits. You could easily spend 2-3 hours here.
Shedd Aquarium: If your kids enjoy marine life, Shedd Aquarium is just across the museum campus and is home to a variety of aquatic animals. It’s located on the lakefront and is another family-friendly spot you can enjoy on your last day.
Lincoln Park Zoo: If you're looking for something outdoors and free, the Lincoln Park Zoo is a great option. It’s a quick drive or taxi ride from downtown, and it’s one of the oldest zoos in the country with a variety of animals and a lovely park area for kids to explore.

Best Time: Early afternoon (to maximize your half-day)

For the evening, consider grabbing a family-friendly dinner at one of Chicago’s famous deep-dish pizza places. Lou Malnati’s or Giordano’s are both great options and located in downtown Chicago. You’ll get a taste of Chicago’s unique pizza style before you wrap up your trip!

Final Tips:

Transportation: Consider using the Chicago Transit Authority (CTA) for getting around, as it's cost-effective and convenient. The "L" trains are great for traveling between neighborhoods.
Time of Year: Since you’ll be visiting in May, the weather should be pleasant, but do check for any specific events happening in the city, as it can get crowded in popular tourist areas.
Dining: Try to make reservations ahead of time for popular spots, especially for dinner, as places like Lou Malnati’s can get busy.

With this itinerary, you’ll cover Chicago’s top attractions while keeping it fun and family-friendly for your kids. Enjoy your trip to the Windy City!

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