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Chicago

4 day itinerary for Chicago

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Make it family friendly

We enjoy great food

Make it tween and teen friendly

We want to tour by boat once

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Itinerary

Chicago is a fantastic city for families, and there’s so much to see and do. Let’s dive into a fun-filled 4-day itinerary that balances great food, exciting activities, and some downtime for everyone to enjoy!

## Day 1: Arrival and Exploring Downtown

Morning:

  • Breakfast at Wildberry Pancakes and Cafe: Start your day with a delicious breakfast. Their pancakes are a must-try, and they have plenty of options for everyone in the family.

Mid-Morning:

  • Millennium Park: After breakfast, head over to Millennium Park. Check out the iconic Cloud Gate (aka "The Bean") and let the kids take some fun photos. Don’t forget to explore the Crown Fountain!

Lunch:

  • Giordano’s for Deep-Dish Pizza: You can’t visit Chicago without trying its famous deep-dish pizza! Giordano’s is a family favorite, and the stuffed pizza is sure to please everyone.

Afternoon:

  • Art Institute of Chicago: If your family enjoys art, this museum is a treasure trove. The kids will love the modern art section, and you can even do a scavenger hunt to keep them engaged!

Evening:

  • Dinner at Portillo’s: Grab some Chicago-style hot dogs and Italian beef sandwiches at this local favorite. The atmosphere is casual and fun, perfect for families.

Night:

  • Navy Pier: After dinner, head to Navy Pier. You can stroll along the pier, enjoy the views of Lake Michigan, and maybe even ride the Ferris wheel for a stunning view of the city skyline at night!

## Day 2: Adventure and Culture

Morning:

  • Breakfast at Lou Mitchell’s: This classic diner is known for its hearty breakfasts and complimentary donut holes. It’s a great way to fuel up for a busy day!

Mid-Morning:

  • Chicago River Architecture Boat Tour: Hop on a boat tour to see the stunning architecture of Chicago from the water. It’s a fun and educational experience that everyone will enjoy!

Lunch:

  • Shake Shack: After your boat tour, grab a quick and tasty lunch at Shake Shack. Their burgers and shakes are a hit with tweens and teens!

Afternoon:

  • Field Museum: Spend the afternoon exploring the Field Museum. The dinosaur exhibits are always a hit, and there are plenty of interactive displays to keep the kids engaged.

Evening:

  • Dinner at The Chicago Diner: Known for its vegetarian and vegan options, this diner has something for everyone. Their “Radical Reuben” is a must-try!

Night:


## Day 3: Science and Shopping

Morning:

  • Breakfast at The Bongo Room: Treat yourselves to some creative breakfast dishes. Their French toast and pancakes are out of this world!

Mid-Morning:

  • Museum of Science and Industry: Spend the morning at this interactive museum. There are tons of hands-on exhibits that will fascinate both tweens and teens.

Lunch:

  • Café at the Museum: Grab a quick bite at the museum café, which offers a variety of options to refuel for the afternoon.

Afternoon:

  • Shopping on Michigan Avenue: After the museum, take a stroll down the Magnificent Mile. There are plenty of shops, and you can stop by the LEGO Store or the Disney Store, which are always a hit with kids.

Evening:

  • Dinner at RPM Italian: Enjoy a family-friendly dinner at this trendy Italian restaurant. The pasta is fresh, and the atmosphere is lively!

Night:

  • Skydeck Chicago: End your day with a visit to the Skydeck at Willis Tower. The views are breathtaking, and stepping out onto the glass ledge is an unforgettable experience!

## Day 4: Relaxation and Departure

Morning:

  • Breakfast at Beatrix: Enjoy a healthy and delicious breakfast at Beatrix. They have great coffee and a variety of breakfast options.

Mid-Morning:

  • Shedd Aquarium: Spend your last morning at the Shedd Aquarium. The exhibits are engaging, and the kids will love the dolphin and sea lion shows!

Lunch:

  • Lunch at the Shedd: The aquarium has a nice café with a variety of options, perfect for a quick lunch before heading out.

Afternoon:

  • Explore Grant Park: If time allows, take a leisurely stroll through Grant Park. It’s a beautiful area to relax and enjoy the scenery before you head home.

Evening:

  • Departure: Depending on your travel plans, you can grab a quick snack or coffee at a nearby café before heading to the airport or your next destination.

And there you have it! A fun-filled, family-friendly itinerary that balances great food, exciting activities, and some relaxation time. Enjoy your trip to Chicago! If you have any questions or need more recommendations, feel free to ask!

Places of interest

Wildberry Pancakes and Cafe Chicago

Wildberry Pancakes and Cafe

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Millennium Park Chicago

Millennium Park

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Giordano’s Chicago

Giordano’s

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Art Institute of Chicago Chicago

Art Institute of Chicago

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Portillo’s Chicago

Portillo’s

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Navy Pier Chicago

Navy Pier

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Lou Mitchell’s Chicago

Lou Mitchell’s

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Chicago River Architecture Boat Tour Chicago

Chicago River Architecture Boat Tour

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Shake Shack Chicago

Shake Shack

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Field Museum Chicago

Field Museum

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The Chicago Diner Chicago

The Chicago Diner

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Lincoln Park Zoo Chicago

Lincoln Park Zoo

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The Bongo Room Chicago

The Bongo Room

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Museum of Science and Industry Chicago

Museum of Science and Industry

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Café at the Museum Chicago

Café at the Museum

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Shopping on Michigan Avenue Chicago

Shopping on Michigan Avenue

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RPM Italian Chicago

RPM Italian

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Skydeck Chicago Chicago

Skydeck Chicago

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Beatrix Chicago

Beatrix

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Shedd Aquarium Chicago

Shedd Aquarium

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Grant Park Chicago

Grant Park

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