Itinerary for 3 day trip to Chicago

Chicago in January can be a bit chilly, but it’s also a magical time to explore the city, especially with a little one in tow. is a fantastic choice, and you’ll be right in the heart of the action. Let’s dive into a fun-filled, family-friendly itinerary for your three days in the Windy City!

Day 1: Exploring Downtown and the Riverwalk

Morning:

Breakfast at the St. Regis: Start your day with a cozy breakfast at the hotel. They have a lovely selection of options, and you can fuel up for the day ahead.
Visit the : After breakfast, head to the . It’s a short drive or a quick ride on public transport. Your little one will be mesmerized by the colorful fish, playful dolphins, and even the penguins! The aquarium is very family-friendly, with plenty of interactive exhibits.

Lunch:

Lunch at the : Grab a bite at the aquarium’s café. They have kid-friendly options, and you can enjoy views of the lake while you eat.

Afternoon:

: After lunch, take a stroll to . Even in winter, the park is a delight! There’s a whimsical play garden that your child will love, and if there’s snow, you might find some fun sledding hills. Just make sure to bundle up!

Evening:

Dinner at : Head to for some classic Chicago deep-dish pizza. It’s a family favorite, and the gooey cheese and buttery crust are sure to please everyone.
Return to the St. Regis: After dinner, head back to the hotel for a cozy night in. Maybe watch a family movie or enjoy some hot chocolate!

Day 2: Museums and Indoor Fun

Morning:

Breakfast at : Start your day with a delicious breakfast at Wildberry, known for its fluffy pancakes and kid-friendly menu.
Visit the : After breakfast, make your way to the . It’s a treasure trove of natural history, and your little one will be fascinated by the dinosaur exhibits and the Ancient Egypt section. There are also plenty of hands-on activities!

Lunch:

Lunch at the : Enjoy a casual lunch at the museum café, which has a variety of options to keep everyone happy.

Afternoon:

Explore the : After lunch, head to the . It’s a bit further away, but totally worth it! There are tons of interactive exhibits, including a giant submarine and a real coal mine. Your child will love the hands-on experiences!

Evening:

Dinner at : For a fun and casual dinner, head to for some Chicago-style hot dogs and Italian beef sandwiches. The atmosphere is lively, and it’s a hit with families.
Return to the St. Regis: After a busy day, relax at the hotel. Maybe take a dip in the pool if you’re up for it!

Day 3: Art, Culture, and a Bit of Shopping

Morning:

Breakfast at the hotel: Enjoy another lovely breakfast at the St. Regis to start your day.
Visit the : After breakfast, take a trip to the Art Institute. While it’s an art museum, there are plenty of colorful and engaging pieces that can capture a child’s attention. Plus, the museum often has family-friendly activities and scavenger hunts!

Lunch:

Lunch at the : Grab lunch at the museum café, which has a nice selection of sandwiches and salads.

Afternoon:

Explore : After lunch, take a stroll through . Check out the famous and let your little one run around in the open spaces. If it’s snowy, it’s a beautiful winter wonderland!
: If you’re up for it, take a walk down the Magnificent Mile for some shopping. There are plenty of stores, and you can pop into places like the LEGO Store, which is always a hit with kids!

Evening:

Dinner at : End your trip with a fun dinner at . The menu is extensive, so there’s something for everyone, and you can indulge in some delicious cheesecake for dessert!
Return to the St. Regis: After dinner, head back to the hotel to pack up and get ready for your departure.

And there you have it! A delightful three-day itinerary that balances fun, exploration, and relaxation, all while keeping your little one entertained. Don’t forget to dress warmly, and enjoy your time in Chicago! If you have any questions or need more suggestions, feel free to ask!