My first trip to the USA became a moment that changed my life. I was amazed by the scale of the country, the contrast of its cities, and the incredible energy of the people. Since then, I have explored America from coast to coast: driven legendary highways, hiked national parks, and discovered hundreds of places you won't find in typical guides. Today I create personalized USA itineraries so you can experience the real America – vibrant, dynamic, and unforgettable. Let me design a trip that fits you perfectly.

Chicago, a vibrant city in Illinois, offers a plethora of kid-friendly activities for families to enjoy. From parks and museums to dining and accommodations, here’s everything you need to know about exploring Chicago with kids.

Best Places to Visit

Parks and Recreation Areas

Millennium Park: Located at 201 East Randolph Street, Millennium Park is home to the iconic Cloud Gate, also known as “The Bean.” Kids will love exploring the reflective surface of this massive sculpture. The park also features the Lurie Garden, providing a peaceful retreat amidst the city’s skyscrapers. In the winter, families can enjoy ice skating at the McCormick Tribune Ice Rink.

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Maggie Daley Park: Situated at 3037 East Randolph Street, Maggie Daley Park is a haven for kids, featuring various play areas tailored to different age groups. The park includes a splash pad for hot summer days, an ice skating ribbon in the winter, and a range of climbing structures and slides.

Navy Pier: A must-visit destination, Navy Pier offers a variety of attractions for families. The Chicago Children’s Museum is a highlight, along with the Centennial Wheel, providing stunning views of the city and lake. Navy Pier also has numerous restaurants, shops, and outdoor performances.

Museums

Museum of Science and Industry: This museum offers interactive exhibits that engage kids in science and industry topics. It’s a place where learning meets fun, with hands-on activities that spark curiosity.

Shedd Aquarium: Located near the Field Museum, the Shedd Aquarium features an oceanarium with dolphin shows, beluga whales, otters, and various aquatic exhibits that fascinate kids and adults alike.

Field Museum: Known for its impressive natural history exhibits, the Field Museum is home to Sue, the most complete T. rex skeleton ever discovered. The museum provides an educational experience with exhibits on dinosaurs, ancient cultures, and more.

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Zoos

Lincoln Park Zoo: A free zoo located in downtown Chicago, Lincoln Park Zoo is perfect for a family day out. It features a variety of animals and is easily accessible within the city.

Brookfield Zoo: Situated in the suburbs of Chicago, the Brookfield Zoo is larger than Lincoln Park Zoo and offers a more extensive range of exhibits and animal encounters.

Theaters and Attractions

Medieval Times: Located about 20 minutes outside of downtown Chicago in Schaumburg, this dinner theater offers a medieval jousting show complete with knights, horses, and a princess. It’s a unique and entertaining experience for the whole family.

Iconic Buildings

Skydeck Chicago: Located on the 103rd floor of the Willis Tower, the Skydeck offers breathtaking views of the city. Kids and adults can experience the thrill of standing on the Ledge, a glass balcony that extends outside the building.

Weather and Best Time to Visit

Chicago experiences four distinct seasons, each with its own unique attractions and activities:

  • Spring (March to May): Mild temperatures and blooming flowers make it a pleasant time to visit parks and outdoor attractions.
  • Summer (June to August): Warm and often hot weather is perfect for beach visits, outdoor festivals, and enjoying the vibrant street life of the city.
  • Fall (September to November): Cooler temperatures and colorful foliage create a scenic backdrop for outdoor activities.
  • Winter (December to February): Cold and snowy, but ideal for ice skating and exploring indoor attractions like museums and theaters.

Where to Stay

The Langham, Chicago: Located near the river, The Langham offers spacious rooms, an indoor pool, and easy access to popular attractions. The hotel also provides a kid-friendly menu and special packages for families.

Four Seasons Hotel Chicago: Situated along the Magnificent Mile, this luxury hotel features an indoor pool, a kid-friendly dining menu, and family-oriented amenities such as kids’ bathrobes and babysitting services.

Embassy Suites by Hilton Chicago Downtown Magnificent Mile: This hotel offers spacious suites with separate living areas, complimentary breakfast, and an indoor pool. Its downtown location is convenient for exploring attractions.

About Us

Since 2015, our website has specialized in individual planning of unique routes, taking into account personal preferences and desires.

Each of you will receive a unique PDF file from us, which contains everything you need: travel routes, car rentals, hotels, the best tourist attractions, attractions for kids and everything you need for a perfect vacation.

During the trip, we are available for you by phone via WhatsApp.

Our personal service provides information from A to Z, taking into account many small details that can become a decisive factor on the way from a wasted trip to an unforgettable vacation.

Our service will make your trip comfortable, save a lot of time on planning and preparation, and most importantly – will allow you to become freer and fully enjoy the pleasure of the trip.

Where to Eat

Medieval Times: A dinner theater that provides a medieval jousting show along with a hearty meal. It is an entertaining and engaging experience for kids.

Sugar Factory: Known for its extravagant desserts and fun ambiance, Sugar Factory offers a full menu that includes colorful sliders, elaborate milkshakes, and a wide variety of sweets.

Giordano’s: Famous for its Chicago-style deep-dish pizza, Giordano’s is a must-visit. Be prepared for a wait, as these pizzas take time to cook, but the experience and taste are worth it.

Portillo’s: A popular spot for Chicago-style hot dogs and Italian beef sandwiches. Kids will love the vibrant atmosphere and tasty food.

4-Day Itinerary

Day 1: Exploring Downtown and Millennium Park

  • Morning: Visit Millennium Park and take photos at The Bean.
  • Afternoon: Explore the Lurie Garden and enjoy a picnic.
  • Evening: Have dinner at Giordano’s for some authentic Chicago deep-dish pizza.

Day 2: Museums and Navy Pier

  • Morning: Visit the Shedd Aquarium and enjoy the dolphin show.
  • Afternoon: Explore the Field Museum and its dinosaur exhibits.
  • Evening: Head to Navy Pier, ride the Centennial Wheel, and dine at one of the pier’s restaurants.
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Day 3: Parks and Zoos

  • Morning: Play at Maggie Daley Park.
  • Afternoon: Visit Lincoln Park Zoo and explore nearby Lincoln Park.
  • Evening: Enjoy a fun and sweet dining experience at the Sugar Factory for dinner.

Day 4: Suburban Adventures and Theater

  • Morning: Start the day with a visit to the Museum of Science and Industry.
  • Afternoon: Take a short trip to Schaumburg for the Medieval Times dinner show.
  • Evening: Watch the jousting show and enjoy a hearty medieval meal.

Tips for Tourists

  1. Book Attractions in Advance: Save time and ensure availability by booking online tickets for popular attractions like the Centennial Wheel and Medieval Times.
  2. Use Public Transportation: Chicago’s extensive and family-friendly public transit system makes it easy to get around the city.
  3. Pack for the Weather: Be prepared for Chicago’s unpredictable weather by packing layers and being ready for sudden changes.
  4. Stay Hydrated: Carry water bottles, especially in the summer, to keep everyone hydrated.
  5. Plan for Meals: Popular restaurants in Chicago can have long waits, so consider making reservations or visiting during off-peak hours.
  6. Take Breaks: Remember to take breaks to rest and recharge, especially if you’re exploring with young kids.
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Chicago is a city full of adventure and excitement for families, with its diverse range of attractions and activities. Whether you’re exploring parks, visiting museums, or indulging in delicious food, Chicago is the perfect destination for a family getaway.

What we propose

Emma Heidi - Itinerary Expert

Emma Heidi


Customer Experience Manager

Take all the stress out of planning your trip!

With our experts, you can create the perfect itinerary for you – complete, comfortable, and tailored to all your dreams, wishes, and needs.

We take care of every little detail, so you can simply focus on enjoying your journey.

We’ve been designing personalized itineraries since 2015, and over the years we’ve created thousands of custom itineraries for happy clients.

Discover our clients’ experiences here

 Save time, avoid confusion – we do the work for you. Our service saves you weeks of searching, reading, comparing, and complicated planning. Instead of wasting endless hours – you receive a ready-to-use, accurate and clear itinerary.

 A tailor-made itinerary – built just for you. Your itinerary is personally designed based on our experts’ real field experience and genuine feedback from hundreds of travelers – including hidden discoveries and insider tips that don’t appear in any travel guide.

 Smart accommodation selection – often saves you hundreds or even thousands of dollars. We help you choose verified and recommended places to stay, checking availability for your exact travel dates. Sometimes we suggest hotels not “in the center,” but in safe, convenient, and highly strategic locations – which can significantly reduce travel costs and save you even thousands of dollars.

 We’re by your side even during the trip. We stay with you throughout your vacation – providing professional help whenever needed. If the weather changes, there’s a strike, a local event, heavy crowds, or any unexpected situation – we are here to update, guide, and adjust your itinerary in real time.

 Easy-to-use itinerary – with direct navigation links. Your itinerary includes direct Waze / Google Maps links – no need to search for parking addresses, no stress, no mistakes. Just tap – and go.


Service cost: from only $420. (Special price for short itineraries up to 5 days). Clients tell us the itinerary saves them costly mistakes, fines, wrong choices – plus exclusive discounts on car rentals, better-priced accommodations, and money-saving local tips.

Want to know if it’s really worth it?

Take a look at the experiences of travelers who built their personal itinerary with us.

Click here and let’s start building the itinerary that will save you time, money, and stress – and turn your vacation into perfection.

Of course, your first inquiry is completely free – with no commitment whatsoever.

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