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Top 25 Things to do In Chicago

by Conor

1. Visit the Art Institute of Chicago

  • Good Points: World-class museum with an extensive collection of artworks.
  • Bad Points: Can be overwhelming due to its size; might require multiple visits.
  • Personal Tips: Don’t miss the Impressionist collection and the Chagall windows. Visit on a weekday to avoid crowds.

2. Stroll through Millennium Park

  • Good Points: Iconic outdoor space featuring the Cloud Gate sculpture (The Bean), beautiful gardens, and cultural events.
  • Bad Points: Often crowded, particularly around The Bean.
  • Personal Tips: Attend a free concert or movie in the summer at the Jay Pritzker Pavilion. Early morning is best for fewer crowds.

3. Explore the Magnificent Mile

  • Good Points: Premier shopping district with a mix of luxury stores, restaurants, and historic buildings.
  • Bad Points: Can be crowded and expensive.
  • Personal Tips: Look out for historic landmarks like the Water Tower. The area is beautifully decorated during the holiday season.

4. Visit the Skydeck in Willis Tower

  • Good Points: Offers breathtaking views of the city from one of the tallest buildings in the Western Hemisphere.
  • Bad Points: Long waiting times; admission can be pricey.
  • Personal Tips: Visit early in the day or during sunset for the best experience. Standing on the glass ledge is a must for thrill-seekers.

5. Enjoy Navy Pier

  • Good Points: Offers entertainment, dining, and great lake views; features an iconic Ferris wheel.
  • Bad Points: Can be touristy and crowded, especially on weekends.
  • Personal Tips: Enjoy a boat tour from here for a unique view of the city. Check for seasonal events and festivals.

6. Visit the Museum of Science and Industry

  • Good Points: One of the largest science museums in the world, with interactive exhibits.
  • Bad Points: A bit far from downtown; can be crowded with school groups.
  • Personal Tips: Don’t miss the U-505 Submarine and the Science Storms exhibit. Allocate a full day if possible, as it’s quite large.

7. Stroll along the Chicago Riverwalk

  • Good Points: Scenic walking path offering great views of the city’s architecture.
  • Bad Points: Can be crowded; some sections are narrower and busier than others.
  • Personal Tips: Take an architectural boat tour from here. Evening walks offer a beautiful perspective with the city lights.

8. Attend a Game at Wrigley Field

  • Good Points: Historic baseball stadium with a great atmosphere.
  • Bad Points: Tickets can be expensive and hard to get for big games.
  • Personal Tips: Even if you’re not a baseball fan, the history and atmosphere are worth experiencing. Visit nearby bars and restaurants for a complete Wrigleyville experience.

9. Visit the Field Museum

  • Good Points: Renowned natural history museum with extensive exhibits, including Sue, the famous T-Rex.
  • Bad Points: Large size can be overwhelming; might require several hours to fully enjoy.
  • Personal Tips: Check out the Ancient Egypt and Evolving Planet exhibits. Mid-week visits are less crowded.

10. Admire the Views from 360 Chicago Observation Deck

  • Good Points: Offers stunning views of the city skyline and Lake Michigan.
  • Bad Points: Can be less known compared to the Skydeck, resulting in shorter wait times but slightly less recognition.
  • Personal Tips: Try the TILT experience for a unique view. Sunset is an ideal time to visit.

11. Explore Lincoln Park Zoo

  • Good Points: One of the oldest zoos in the country; free admission.
  • Bad Points: Can be crowded, especially on weekends and holidays.
  • Personal Tips: Visit early in the morning to avoid crowds. The zoo lights during the holiday season are a must-see.

12. Discover the Shedd Aquarium

  • Good Points: Houses a vast array of marine life in beautifully designed habitats.
  • Bad Points: Ticket prices can be high; popular exhibits often have long lines.
  • Personal Tips: Buy tickets online to skip the line. The aquatic show is worth watching.

13. Walk the Lakefront Trail

  • Good Points: Offers picturesque views of Lake Michigan and the city skyline.
  • Bad Points: Can be crowded with joggers, bikers, and tourists, especially on nice days.
  • Personal Tips: Rent a bike for a quicker way to enjoy the trail. Don’t miss the beaches along the way.

14. Visit the Adler Planetarium

  • Good Points: America’s first planetarium with engaging space and astronomy exhibits.
  • Bad Points: Some exhibits may seem dated; geared more towards children.
  • Personal Tips: Attend a sky show in one of the theaters. The view of the Chicago skyline from here is spectacular.

15. Explore the Chicago Cultural Center

  • Good Points: Offers free music, dance, and theater events; home to beautiful stained-glass domes.
  • Bad Points: Exhibition quality can vary; not all events might be of interest.
  • Personal Tips: Check the schedule for free concerts and exhibits. Don’t miss the Preston Bradley Hall Tiffany dome.

16. Take an Architectural River Cruise

  • Good Points: Offers a unique perspective on Chicago’s renowned architecture.
  • Bad Points: Can be pricey; popular times and days book up quickly.
  • Personal Tips: Book in advance and consider a sunset cruise for stunning views. Bring a jacket as it can get breezy on the river.

17. Enjoy the Nightlife in River North

  • Good Points: Area known for its vibrant nightlife, with many bars and clubs.
  • Bad Points: Can be expensive; some venues have dress codes and cover charges.
  • Personal Tips: Explore the cocktail bars for a more upscale experience. Some restaurants in the area turn into lounges after dinner hours.

18. Visit the Chicago History Museum

  • Good Points: Offers a deep dive into the rich history of Chicago.
  • Bad Points: Smaller and more specialized than other museums.
  • Personal Tips: Check out the exhibits on the Great Chicago Fire and the city’s jazz history. The museum is often less crowded than others.

19. Attend a Performance at the Chicago Theatre

  • Good Points: Historic venue known for its grand architecture and diverse shows.
  • Bad Points: Tickets for popular shows can be expensive.
  • Personal Tips: Even if you don’t see a show, take a picture in front of the iconic “Chicago” marquee. Guided tours are available to explore the interior.

20. Explore Grant Park and Buckingham Fountain

  • Good Points: Known as “Chicago’s front yard,” featuring gardens, sculptures, and the impressive Buckingham Fountain.
  • Bad Points: Can be crowded during special events and summer weekends.
  • Personal Tips: The fountain’s evening light shows are a must-see. It’s a great spot for picnics and relaxing.

20. Explore Grant Park and Buckingham Fountain

  • Good Points: Known as “Chicago’s front yard,” featuring gardens, sculptures, and the impressive Buckingham Fountain.
  • Bad Points: Can be crowded during special events and summer weekends.
  • Personal Tips: The fountain’s evening light shows are a must-see. It’s a great spot for picnics and relaxing.

21. Visit the Robie House

  • Good Points: A masterpiece of Frank Lloyd Wright’s Prairie style architecture.
  • Bad Points: Requires guided tour for full access; located in Hyde Park, a bit away from downtown.
  • Personal Tips: Book a tour in advance. Combine your visit with a trip to the nearby University of Chicago campus.

22. Explore the Garfield Park Conservatory

  • Good Points: One of the largest conservatories in the nation; lush greenery and exotic plants.
  • Bad Points: Located away from the city center; neighborhood can be less tourist-friendly.
  • Personal Tips: Visit during one of their seasonal shows or events. It’s a great indoor activity for cold or rainy days.

23. See a Show at Second City

  • Good Points: Legendary comedy club known for launching the careers of many famous comedians.
  • Bad Points: Popular shows sell out quickly; some content might not suit all tastes.
  • Personal Tips: Book tickets in advance. Stick around after the show for the possibility of a free improv set.

24. Visit the Oriental Institute

  • Good Points: Part of the University of Chicago, featuring fascinating exhibits on the ancient Near East.
  • Bad Points: More academic and less interactive than other museums.
  • Personal Tips: Don’t miss the Mesopotamian gallery. The museum is free (suggested donation), making it a great budget-friendly option.

25. Attend a Performance at the Lyric Opera of Chicago

  • Good Points: One of the world’s great opera companies, offering high-quality performances.
  • Bad Points: Opera may not appeal to everyone; tickets can be pricey.
  • Personal Tips: Look for special offers or less popular performances for better ticket prices. The building itself is worth seeing for its architecture.
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