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!

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Travel plan

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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!

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

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.

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.

Chicago Adventure: Cultural Foodie Fun

A trip to Chicago, known as the "Windy City," is a perfect choice for culture-seekers and foodies alike. Filled with architectural gems, world-renowned museums, and diverse neighborhoods, there's no shortage of things to explore. Don't leave without trying Chicago-style deep-dish pizza and taking a stroll along the picturesque Lake Michigan shoreline.

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.