Chicago’s lakefront is one of the city’s best features: 18 miles of parks, beaches, and trails.

- Lakefront Trail — Walk, run, or bike along Lake Michigan with skyline views.

- Lake Michigan Beaches — If the weather cooperates, these great for relaxing or people‑watching.

- Lincoln Park — A huge stretch of green space with ponds, gardens, and walking paths.

- Lincoln Park Conservatory — A beautiful (and free) Victorian‑era greenhouse.

- Garfield Park Conservatory — A world-class botanical garden. Admission is $10 and reservations are highly recommended.

- Chicago Riverwalk — A lively waterfront path with cafés, public art, and great views.

Chicago is home to world-class museums, including:

- The Art Institute of Chicago — One of the best art museums in the world, home to American Gothic, Nighthawks, and Monet’s Water Lilies.

- The Field Museum — Natural history, dinosaurs, and “Sue,” the famous T. rex skeleton.

- Shedd Aquarium — Beluga whales, penguins, and other aquatic exhibits.

- Museum of Science & Industry — A submarine, a coal mine, and a tornado simulator; tons of fun if you want to revisit childhood.

- Chicago Cultural Center — Free exhibits and the world’s largest Tiffany glass dome.

Chicago is the birthplace of the skyscraper, and the architecture scene is unmatched.

- Architecture Boat Tour — The most iconic Chicago activity; highly recommended if you are a first-time visitor to Chicago.

- Skydeck at Willis Tower — Step out onto the glass ledge 1,353 feet above the city.

- 360 Chicago at the Hancock — Incredible views, plus the TILT experience.

- Millennium Park — Home to Cloud Gate (“The Bean”), gardens, and outdoor art.

Each neighborhood has its own personality, and many are close to the venue.

- Andersonville — Just north of Edgewater; known for boutiques, cafés, Swedish heritage, and great restaurants.

- Wicker Park & Bucktown — Trendy shops, cocktail bars, and some of the city’s best dining.

- Lincoln Park — Tree‑lined streets, the zoo, and plenty of shopping.

- The Loop — Chicago’s downtown core with theaters, architecture, and Millennium Park.

Chicago’s food scene is legendary — and not just for deep dish.

- Deep Dish Pizza — A must‑try for visitors (Pequod’s is our suggestion, though it is a bit niche compared to other options).

- Chicago‑Style Hot Dogs — Don't ask for ketchup!

- Italian Beef Sandwiches — Brent's suggestion is "dipped" with hot peppers.

- World‑Class Restaurants — From Michelin‑starred tasting menus to small neighborhood gems.

- Cocktail Bars & Breweries — Logan Square, West Loop, and River North have great options.

- Edgewater & Andersonville — Fantastic bakeries, brunch spots, and global cuisine close to the wedding venue.

If you want to catch a show or experience Chicago’s creative side:

- Chicago Theatre — Iconic marquee with an elegant lobby, majestic staircase, and beautiful auditorium complete with murals above the stage and on the ceiling.

- Broadway in Chicago — Touring Broadway shows perform in various historic theaters.

- Second City — Legendary comedy club where many SNL stars got their start.

- Jazz & Blues Clubs — Green Mill (a classic), Kingston Mines, and Buddy Guy’s Legends.