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Kayak Chicago is the top-rated full-service watersport outfitter in Chicago. They provide kayaks, paddleboards, and electric boats for those who want to experience the water uniquely. You can go on a guided tour or explore the city's iconic architecture at your own pace with a single or double kayak rental. For those who want to relax and enjoy stunning skyline views, North Ave. beach is the perfect spot to take a leisurely float. Alternatively, you can visit Montrose Beach, one of Chicago's best-kept secrets, and try paddleboarding. The team at Kayak Chicago is committed to your safety and ensuring you have the best possible experience on the water. Their experienced guides and staff help you have a memorable paddling adventure. Whether you're discovering a new passion for paddling, learning fascinating facts about the city's history and architecture, or picking up new skills to take with you on future adventures, they are there to help. No matter your experience level, they will ensure you learn and grow as a paddler. Remember to bring sunblock, sunglasses, and a hat to protect yourself from the sun. Stay hydrated and energized with plenty of water and snacks.

If you are a fan of blues music, you should visit Kingston Mines during your trip to Chicago. This jazz and blues bar is one of the oldest establishments in the city and offers an intimate setting for live music performances. The venue has been presenting the best acts since 1968 and has a legendary reputation for hosting some of the finest live music performances in Chicago. It has won the "Best Blues Club" award at the Chicago Music Awards for 13 years. At Kingston Mines, you can enjoy live, authentic jazz and blues music on two stages. The venue also offers a wide selection of drinks, including beer buckets, wine, and cocktails. And if you're feeling hungry, check out Doc's Rib Joint - the in-house restaurant that serves mouthwatering barbecue, chicken, burgers, seafood, ribs, and various tasty sides and appetizers.

If you want a thrilling adventure on the Navy Pier, you must check out the Amazing Chicago Funhouse Maze. This attraction is a twisting labyrinth of mirrors, illusions, and surprises that will leave you dizzy with excitement. Covering over 4,000 square feet of tunnels and mazes, the Maze is a must-do for people of all ages. The Amazing Chicago Funhouse Maze has been open since 2001 and is a popular attraction among guests. It features classic funhouse elements such as a spinning tunnel and mirror maze, as well as new features like an infinity lightroom and glow light artwork. You will find plenty of unique photo opportunities throughout the Maze that you can't afford to miss.

Hawthorne Race Course is a venue that offers both live racing and simulcasting. It is a thoroughbred horse racetrack with a one-mile dirt oval and a seven-furlong turf oval. The homestretch on the main track is 1,320 feet long, making it one of the longest in the country. Founded in 1891, Hawthorne Race Course is the oldest sporting venue in Illinois for horse racing, considered America's original sport. The business is family-owned and operated, now in its 4th generation, and has been hosting racing events on the City's border for over a century. The track is famously known as "Chicago's hometown track." Hawthorne is also the only race course in the nation that hosts both Thoroughbred and Standardbred racing. Additionally, they have the largest network of off-track betting bars in Illinois and offer two PointsBet Sportsbooks and a sportsbook at the track.