Chicago Adventures: 5 Days of Family Fun on a Budget

Discover the wonders of the Windy City on a family-friendly adventure in Chicago!

19 July 2023

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.

Travel plan

Getting latest place information
Day 1

Exploring the Windy City's Delights

  • Start the day with a hearty breakfast at Waffles Café, where crispy waffles and fluffiness will shine a sunny light on your taste buds.
  • Take a leisurely stroll along the Magnificent Mile, where towering skyscrapers and glamorous shops will make you feel like the stars are dancing above you.
  • Get lost in the Art Institute of Chicago, a treasure trove of art from all around the world. Don't forget to say hi to the infamous "American Gothic" couple!
  • Treat the fam to a slice of deep-dish pizza heaven at Lou Malnati's Pizzeria. It's cheesy, saucy goodness that will have you begging for more.
  • End the day on Navy Pier, with rides, mesmerizing views of Lake Michigan, and fireworks that will make your heart sing.
Day 2

Dive into Cultural Feasts

  • Begin your day with a delightful brunch at Yolk, where fluffy omelets and stacks of pancakes will set your soul on fire.
  • Visit the Museum of Science and Industry, a wonderland of interactive exhibits that will have your little ones' imaginations running wild.
  • Meander through Millennium Park and marvel at the reflective Cloud Gate sculpture, lovingly known as "The Bean."
  • Enjoy a scrumptious dinner at Portillo's, a Chicago institution that boasts mouthwatering hot dogs and Italian beef sandwiches.
  • Catch a show at the famous Second City, where comedic geniuses have honed their craft. Prepare to laugh until your cheeks ache.
Day 3

Unleash Your Inner Sports Fan

  • Start the day with a quick breakfast at Firecakes Donuts because life is too short to skip dessert for breakfast.
  • Dive into the sporting culture at Wrigley Field and catch a ballgame. Root for the Cubs or just marvel at the magical atmosphere.
  • After the game, head to Chicago's iconic Lincoln Park Zoo, home to adorable animals and stunning views of the city skyline.
  • Refuel at Giordano's, the land of stuffed pizza dreams. The gooey cheese and flaky crust will have you reaching pizza nirvana.
  • Embrace your competitive side at WhirlyBall, a wild and wacky game that combines bumper cars, lacrosse, and pure, unadulterated fun.
Day 4

A Journey Through History and Nature

  • Start the day with a caffeine fix at Intelligentsia Coffee, a haven for all coffee lovers.
  • Take a trip back in time at the Field Museum, where you can explore ancient mummies, dinosaur skeletons, and get up close with Sue, the T-Rex.
  • Escape the city buzz and immerse yourself in the beauty of Garfield Park Conservatory, a lush sanctuary filled with vibrant flowers and serenity.
  • Refuel at Lou Malnati's for more deep-dish magic because once is never enough.
  • End the day with a breathtaking architectural boat tour along the Chicago River, where the city's skyline is the star of the show.
Day 5

Farewell with Flavor

  • Begin your final day in Chicago with brunch at Ann Sather, a charming Swedish diner serving heavenly cinnamon rolls that will make your heart dance.
  • Explore the Shedd Aquarium, a watery wonderland where majestic marine creatures swim alongside your imagination.
  • Wander through Grant Park and bask in the beauty of Buckingham Fountain, known as Chicago's "front door."
  • Indulge in Chicago's famous popcorn at Garrett Popcorn Shops, where sweet and savory flavors collide in a popcorn extravaganza.
  • Bid adieu to the Windy City with dinner at The Purple Pig, where Mediterranean-inspired dishes will leave your taste buds singing and your heart longing for more.

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

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.

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.

The Ultimate 3-Day Chicago Adventure

Chicago boasts an impressive skyline and rich cultural diversity that attracts visitors from all over the world. Iconic landmarks such as the Willis Tower and Millennium Park provide excellent photo opportunities, while a stroll along the Magnificent Mile offers an extensive array of shopping, dining, and entertainment options. For a taste of Chicago's famous cuisine, deep-dish pizza and Chicago-style hot dogs are a must-try.

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.