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
Sophie Watts
US Travel Writer
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.
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- 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.
- 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.
- 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.
- 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.
- 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.
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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.