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

Discover the Windy City's wonders, embrace the family fun in Chicago.

19 July 2023

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.

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Travel plan

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Day 1

Windy City Welcome

  • Check into The Ritz-Carlton, a luxurious hotel where your family will be treated like VIPs from the moment you step through the door.
  • Visit Millennium Park, where you can snap photos of the iconic Cloud Gate sculpture, aka "The Bean," and let the kids run wild in the Crown Fountain.
  • Head to Navy Pier, filled with thrilling rides, delicious food stalls, and even a Ferris wheel that offers incredible views of Chicago's skyline.
  • Take a stroll down the Magnificent Mile, where you'll find shops galore for a little retail therapy.
  • End the day with a taste of classic Chicago deep-dish pizza at Giordano's Pizzeria, where cheesy wonders await.
Day 2

The Tastes of Chicago

  • Start your day with a hearty breakfast at Yolk, a local favorite known for its creative twists on classic morning meals.
  • Explore the charming Lincoln Park Zoo, where you can spot exotic animals and enjoy the beauty of nature, all for free!
  • Head to Portillo's for lunch, a Chicago institution serving up mouthwatering hot dogs and Italian beef sandwiches.
  • Dive into the city's cultural scene at the Art Institute of Chicago, home to masterpieces from Monet, Picasso, and many more.
  • Indulge in a deep-fried delight for dinner at The Purple Pig, a lively spot boasting a menu of Mediterranean-inspired small plates.
Day 3

Urban Adventures

  • Start your day with a delicious breakfast at Lou Mitchell's, a diner that's been fueling Chicagoans since 1923 with fluffy pancakes and hearty omelets.
  • Take a walk along the Chicago Riverwalk, where you can admire the city's stunning architecture and enjoy boat tours.
  • Immerse yourself in history at the Chicago History Museum, where interactive exhibits will transport you back in time.
  • Catch a baseball game at Wrigley Field, home to the beloved Chicago Cubs don't forget to grab a hot dog and cheer with the crowd!
  • Complete your day with dinner at Girl & The Goat, an award-winning restaurant serving up inventive, globally-inspired dishes.
Day 4

Farewell, Chicago

  • Start your day with a delightful breakfast at Wildberry Pancakes and Cafe, known for their fluffy stacks of pancakes and creative breakfast options.
  • Explore the Shedd Aquarium, where you can marvel at breathtaking marine life, including dolphins, penguins, and sharks.
  • Experience the thrill of the Chicago River architecture tour, cruising along the glittering waterway while learning about the city's stunning buildings.
  • Enjoy a lunch of delectable Mexican street food at Antique Taco, known for their imaginative taco combinations and vibrant flavors.
  • Before saying goodbye to the Windy City, catch an entertaining show at The Second City, where comedy legends like Tina Fey and Steve Carell got their start.

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.

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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.

Chicago on a Budget: 3-Day Adventure Guide

Chicago is a vibrant and exciting city that can be enjoyed on a limited budget. Visitors can take in panoramic views from the top of Willis Tower, explore the diverse neighborhoods of Lakeview and Wicker Park, and visit the free-admission museums such as the Art Institute of Chicago. To save on accommodation costs, travelers can opt for budget-friendly hostels or seek out affordable Airbnb rentals.

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 on a Budget: The 5-Day Adventure

Exploring Chicago on a limited budget is possible with the city's many free attractions including Millennium Park, Navy Pier, and the Lincoln Park Zoo. Budget-friendly accommodations can be found in the city's hostels and Airbnb's located in the trendy neighborhoods of Wicker Park and Logan Square. Delicious local cuisine at affordable prices can also be found in the city's diverse dining scene ranging from deep-dish pizza to ethnic street food.