Chicago Fun Frenzy: Explore, Indulge, and Immerse!

Explore the charm of Chicago with your loved ones – a family adventure awaits!

19 July 2023

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.

Save and get deals

Day trip plan

Getting latest place information
Day

Discovering the Windy City

  • Rise and shine, your adventure begins at the bean! Take a selfie with Chicago's iconic Cloud Gate sculpture in Millennium Park.
  • Hop on a boat tour along the Chicago River to experience the beautiful architecture and hear fascinating stories of the city's rich history.
  • Fill your bellies with a classic Chicago deep-dish pizza at the famous Giordano's. Warning: this cheesy delight might change your life forever!
  • Burn off those pizza calories with a visit to Navy Pier. Ride the Ferris wheel, play mini-golf, or get lost in the funhouse – the options are endless!
  • Time to channel your inner detective at the Chicago Crime Museum. Uncover the city's shady past, from Al Capone's reign to the notorious St. Valentine's Day Massacre.
  • End your day with a theater extravaganza! Catch a Broadway show at the Cadillac Palace Theatre and let the magic of the stage transport you into another world.

Length of stay

1 day 2 days 3 days 4 days 5 days

Type of trip

Standard trip Budget Family Friendly Romantic Stag do

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.

Destination

Chicago

Welcome to the Windy City, where the people are friendly, the pizza is deep, and the weather is unpredictable enough to keep things interesting. Just make sure to hold onto your hats (and your deep dish) while you're here.

 Save and get deals

Number of days

1 2 3 4 5

Type of trip

Standard trip Budget Family Friendly Romantic Stag do

More travel plans

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.

5-Day Romantic Getaway in Chicago, USA

A romantic trip to Chicago, United States is the perfect opportunity to explore the Windy City together. You can take a stroll along the picturesque Lake Michigan shoreline, indulge in mouth-watering cuisine at award-winning restaurants, and take in the breathtaking views from the Willis Tower. With a wide range of cultural and entertainment options, Chicago provides the ideal backdrop for a memorable romantic getaway.

Windy City Wonders: A 4-Day Family Adventure in Chicago!

Experience the vibrant city of Chicago on a family friendly trip filled with unforgettable memories. Explore the iconic Millennium Park, where kids can splash in the Crown Fountain or marvel at the reflective Bean sculpture. Indulge in delicious deep-dish pizza, visit the Shedd Aquarium or catch a baseball game at Wrigley Field for an action-packed getaway in the Windy City.

Chicago on a Budget: Three Days of Fun!

A family friendly trip to Chicago, United States offers an exciting blend of entertainment and education for all ages. Explore the iconic Navy Pier with thrilling rides, beautiful gardens, and stunning lake views. Immerse yourself in the city's rich history by visiting unique museums like the Shedd Aquarium, Field Museum, and the interactive Chicago Children's Museum.