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 on a Budget: A Day of Adventure

Visiting Chicago on a limited budget is still possible with some careful planning. Opt for budget-friendly accommodation options such as hostels or Airbnbs in less touristy neighborhoods. Take advantage of public transportation and free activities such as visiting Millennium Park, the Lincoln Park Zoo, and exploring the city's diverse neighborhoods for a fun and affordable trip to Chicago.

Discover Chicago: A Family-Friendly Adventure on a Budget

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!

Chicago Adventures: 5 Days of Family Fun on a Budget

A family trip to Chicago offers a unique blend of culture, entertainment, and history. Start your adventure with a visit to famous attractions such as Millennium Park, where kids can explore the interactive Crown Fountain or take photos with the iconic Cloud Gate sculpture. Don't miss out on a fun-filled day at Navy Pier, where you can ride the Ferris wheel, enjoy live performances, and indulge in delicious food from various vendors.

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.