Deep-dish pizza, lakeside vibes, and sky-high architecture make this Midwestern gem a must.

Chicago offers everything: jaw-dropping architecture, a buzzing lakefront, world-class food, iconic sports, and some of the friendliest people you’ll meet. Whether you’re paddling through the skyline, chilling in Millennium Park, or eating your way across the city – Chicago is a cultural must-visit during your post-camp travels.

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Big city energy, friendly vibes

After Summer Camp ends, the adventure really begins — and Chicago is the perfect place to start. Known as the “Windy City,” this energetic, welcoming and diverse metropolis blends everything we love about America: epic food, world-famous architecture, live music, lake beaches and unbeatable nightlife.

Even if you only have a couple of days here during your 30 days of post-camp travel, we’ve picked out the must-dos, must-sees and must-eats that’ll make Chicago one of your favourite US cities ever.

Explore from the water

Start your trip by heading downtown to the Chicago Riverwalk. For a unique way to see the city’s skyline, hop on the Water Riders Kayak Tour. It’s a bit of a workout but paddling past skyscrapers and historic buildings from the water is seriously cool.

Prefer to sit back and feel the wind in your hair? Jump aboard a Seadog Speedboat Tour. You’ll cruise through downtown before blasting out onto Lake Michigan for a high-speed thrill ride.

Navy Pier is Chicago’s ultimate lakeside playground. With 50 acres of attractions, this historic pier is home to the famous Centennial Ferris Wheel, mini-golf, museums, shops, and lakeside dining spots. It’s great for a group day out or just chilling by the water with new camp friends.

Eat like a Chicagoan

Chicago is a foodie’s dream. Don’t leave without trying the city’s iconic eats:

  • Portillo’s (W. Ontario Street) – Grab a Chicago Dog or an Italian Beef sandwich. It’s a local institution and the vibe is always buzzing.
  • Pizzeria Uno (E. Ohio Street) – Where deep-dish pizza was born. Thick, cheesy, saucy… and worth the wait.
  • The Bongo Room (North Milwaukee Avenue) – Chocolate French Toast Towers? Yes, please.
  • Smoque BBQ – Ribs, slaw and smoky goodness. Go hungry.
  • Billy Goat Tavern – A quirky, no-frills burger joint with a cult following and a lot of personality.

For the sports fans

Chicago is sports mad. Here’s where to get your fix:

  • Wrigley Field – Home of the Chicago Cubs. If you’re lucky, catch a weekend game and soak up the old-school baseball energy.
  • Soldier Field – Home of the Chicago Bears (NFL).
  • United Center – See the Chicago Bulls (NBA) or Blackhawks (NHL) in action and walk in MJ’s footsteps.
  • Chicago Fire – For MLS fans, grab tickets to watch some of the USA’s best soccer.

Willis Tower – Sky-high thrills

Ready to conquer your fear of heights? Take the lift to the Skydeck at Willis Tower, once the tallest building in the world. Step out onto The Ledge—a glass box extending over 1,300 feet above street level. It’s terrifying. It’s epic. It’s Insta-worthy.

Chill time at Millennium Park

After all that energy, take a breather in Millennium Park. Snap a selfie at The Bean (Cloud Gate), catch a free concert, or even take a dip in Lake Michigan at one of the downtown beaches. This park is buzzing all summer long with over 500 free events from movies to music and everything in between.

After dark vibes

When the sun sets, Chicago comes alive. Start your night at the iconic House of Blues with live jazz and blues, then explore the Lincoln Park area for a buzzing student crowd and late-night dance floors.

Top bars to check out:

  • The Beaumont – Two floors of DJ sets and packed dance floors.
  • The Apartment – Looks like a retro flat, parties like a club.
  • The Store – Great tunes, cheap drinks, laid-back energy.