Discover Chicago: A Family-Friendly Adventure on a Budget

Discover the Windy City's thrilling mix of family-friendly attractions and create unforgettable memories in Chicago, USA!

19 July 2023

A family-friendly trip to Chicago offers a perfect blend of fun and educational activities. Explore the interactive exhibits at the renowned Field Museum, embark on a scenic boat tour along the Chicago River, and get a stunning, panoramic view of the city from the Skydeck Chicago. Don't forget to indulge in some deep-dish pizza and visit the beloved Lincoln Park Zoo during your visit!

Travel plan

Getting latest place information
Day 1

Exploring the Windy City's Wonders

  • Welcome to the vibrant city of Chicago, where the sights are as magnificent as Oprah's shoe collection!
  • Check into the family-friendly Swissotel Chicago, a luxurious hotel that's more stylish than a jazzed-up hot dog (and that's saying something!).
  • Start your day with a visit to Navy Pier, a carnival on steroids! With its towering Ferris wheel and carousel, it's like Willy Wonka's playground.
  • Head to Millennium Park where you can strut your stuff with "The Bean," a reflective sculpture that gives you a funhouse mirror view of the city.
  • Lunchtime! Grab a slice of Chicago-style deep-dish pizza at Lou Malnati's, where the cheese flows like a river and the sauce is as bold as a Cubs fan in the bleachers.
  • Embark on an architectural boat tour along the Chicago River, where you'll geek out over sky-high skyscrapers like a modern-day Sherlock Holmes.
Day 2

Culture and Cuisine: A Perfect Pairing in the Windy City

  • Rise and shine! Start your day at the Field Museum, where dinosaurs reign supreme and ancient artifacts whisper secrets from the past.
  • Take a stroll through the Art Institute of Chicago, where masterpieces by Van Gogh, Monet, and Picasso will make you feel like a tiny art connoisseur on a giant color palette.
  • Lunch at Portillo's, a local institution serving up juicy Chicago-style hot dogs and Italian beef sandwiches that'll make you shout "Mamma Mia!"
  • Discover the enchanting Shedd Aquarium, where you can swim with dolphins (not really, but let's pretend!) and marvel at sea creatures that are cooler than a Cubs game in October.
  • End your Chicago adventure with a sweet treat at Garrett Popcorn Shops, where popcorn is elevated to a whole new level with flavors like "Chicago Mix" (cheddar and caramel) that'll make your taste buds do the tango.
  • Remember, in Chicago, the only thing colder than the winter weather is the fierce love locals have for their city. So grab your deep-dish dreams and dive into the Windy City's charm!

How to get there

Plane

The best way to get to Chicago by plane is to fly into O'Hare International Airport or Midway International Airport, both of which are served by major airlines from most major cities in the world. You can check prices and schedules on websites like Expedia or Kayak.

Car

The best way to get to Chicago by car is to take one of the major highways, such as I-90 or I-94, which both run through the city. However, be aware of traffic congestion during peak travel times.

Train

The best way to get to Chicago by train is to take an Amtrak train, which connects the city to other major cities in the United States, such as New York, Washington D.C., and Los Angeles. The main train station in Chicago is Union Station.

Boat

The best way to get to Chicago by boat is to take a ferry from Navy Pier to locations such as Michigan City or St. Joseph. However, this mode of transportation is not as common as the others and may have limited availability depending on the season.

Bus

The best way to get to Chicago by bus is to take a Greyhound bus, which connects the city to most major cities in the United States. The main bus station in Chicago is the Greyhound Station.

More travel plans

Two-Day Windy City Romance Guide

Chicago offers a perfect backdrop for a romantic trip with its picturesque skyline and waterfront views. The city’s rich history, lively culture, and delicious food make it an ideal destination for couples who want to experience the ultimate romantic getaway. Take a stroll on the stunning Lakefront Trail, grab some deep-dish pizza, and catch a show at one of its renowned theaters for an unforgettable romantic trip.

5-Day Adventure Guide to Chicago, USA

Chicago is a bustling metropolis on the shores of Lake Michigan, known for its architecture, food, and culture. Tourists can explore the city's many museums and parks, including the Art Institute of Chicago and Millennium Park. Be sure to sample the city's famous deep-dish pizza and catch a game at Wrigley Field or Soldier Field.

Chicago Fun Frenzy: Explore, Indulge, and Immerse!

A trip to Chicago offers a plethora of family-friendly activities and attractions. Explore the iconic Navy Pier where you can enjoy rides, games, and spectacular views of Lake Michigan. Immerse yourselves in the vibrant culture of the city by visiting Millennium Park, home to famous landmarks like "The Bean" and a host of interactive public art installations. Finally, don't forget to indulge in Chicago's deep-dish pizza and explore the numerous museums and zoos that cater to children's interests.

Chicago in 4 days: Romance, Art, and Adventure

A romantic trip to Chicago begins with a stroll along the picturesque Riverwalk, taking in the stunning views of the city’s skyline. Embark on a journey to the top of the Willis Tower to marvel at the spectacular panorama or catch a show at the iconic Chicago Theatre. Relax with a glass of wine or craft cocktail in one of the city’s rooftop bars, or indulge in a romantic dinner at one of its many acclaimed restaurants.