Guest Post by Amy Boyle
Meet Amy Boyle
Amy Boyle is an internationally published photographer and entrepreneur. Along with her husband Jeff and four grown sons, Amy has made Chicago home for over 28 years. Enjoy Amy’s recommendations of what makes Chicago her kind of town!
Q: Why is visiting Chicago so great?
A: Chicago is known for its stunning architecture, beautiful skyline, and vibrant cultural scene. It offers a rich blend of attractions, including world-class museums, delicious cuisine, live music, theater, sports events, and so much more. The city has a unique character, with distinct neighborhoods each offering its own charm and personality. If you like to know what’s going on in all 77 neighborhoods of Chicago, I recommend checking out Block Club Chicago.
Q: What’s the best time of year to visit Chicago?
A: The best time to visit Chicago is during the spring (April to May) and fall (September to October) when the weather is mild and pleasant. However, if you enjoy festivals and events, summer (June to August) can be a great time with various outdoor activities. Keep in mind that winters in Chicago can be very cold, but the city also has a unique charm during the holiday season.
Q: Best airport to fly in/out of? Any specific airport tips?
A: Chicago has two major airports: O’Hare International Airport (ORD) and Midway International Airport (MDW). O’Hare is larger and serves more international flights, while Midway is smaller and handles more domestic flights. Both airports are well-connected to the city center via public transportation, and there are various transportation options available, including taxis, ride-sharing services, and airport shuttles.
Q: Once you arrive at the airport, is it best to rent a car or take Uber everywhere?
A: The best transportation option in Chicago depends on your preferences and itinerary. If you plan to primarily stay within the city, it’s often more convenient to rely on public transportation, such as buses and trains (CTA), or use ride-sharing services like Uber and Lyft. Parking can be expensive and limited in downtown Chicago. However, if you plan to explore areas outside the city or have specific transportation needs, renting a car might be more suitable.
Q: What’s the best area to stay in Chicago? Any specific hotel recommendations? Or is it best to rent a place on Airbnb?
A: The best area to stay in Chicago depends on your interests and the purpose of your visit. Some popular neighborhoods for tourists include Downtown, the Loop, River North, and the Magnificent Mile, which offer easy access to attractions, shopping, and dining. If you prefer a more residential and eclectic atmosphere, consider neighborhoods like Wicker Park, Lincoln Park, or Lakeview.
For hotel recommendations, some highly-rated options in Chicago include The Langham, The Peninsula, Four Seasons, The Gwen, and The Talbott Hotel. Alternatively, if you prefer a more local experience, renting a place on Airbnb can provide you with a wider range of accommodation options in different neighborhoods.
Q: What are some must-do activities while in Chicago?
A: Some must-do activities in Chicago include:
Taking an architecture boat tour on the Chicago River.
Exploring Millennium Park and visiting the famous “Bean” sculpture (Cloud Gate).
Visiting the Art Institute of Chicago, one of the oldest and largest art museums in the U.S.
Enjoying the views from the Willis Tower Skydeck or the 360 Chicago Observation Deck.
Catching a show or performance at the Chicago Theatre District. Broadway in Chicago
Strolling along Navy Pier and experiencing its attractions and fireworks.
Sampling Chicago’s iconic deep-dish pizza and trying other local cuisine. Lou Malnati’s and Pequods are my favorites!
Q: What are the top 3-5 museums to visit while in Chicago?
A: Chicago is renowned for its museums. Here are some top recommendations:
The Art Institute of Chicago: A world-class art museum with a vast collection spanning various periods and styles.
Museum of Science and Industry: Offers interactive exhibits on science, technology, and innovation.
Field Museum: Features natural history exhibits, including the famous T. rex skeleton named Sue.
Shedd Aquarium: One of the largest indoor aquariums in the world, housing a diverse range of marine life.
Adler Planetarium: Perfect for astronomy enthusiasts, with exhibits on space exploration and a planetarium.
Q: How family-friendly is Chicago? What are some top activities to do with kids?
A: Chicago is a family-friendly city with plenty of activities for kids. Some top attractions for families include:
The Lincoln Park Zoo: A free zoo with a wide variety of animals and family-friendly events.
The Chicago Children’s Museum: Offers interactive exhibits and educational activities for children of all ages.
Maggie Daley Park: A large park with playgrounds, mini-golf, ice skating, and a climbing wall.
Navy Pier: Provides entertainment options such as the Ferris wheel, boat rides, and an IMAX theater.
The Peggy Notebaert Nature Museum: Focuses on nature and wildlife, with interactive exhibits and a butterfly haven.
Q: Tell me about the performing arts scene in Chicago. Best places to see live music, dance, and theater?
A: Chicago has a thriving performing arts scene. Here are some renowned venues for live music, dance, and theater:
Chicago Symphony Center: Home to the Grammy-winning Chicago Symphony Orchestra.
The Second City: Famous for its improvisational comedy shows and launching many notable comedians.
Steppenwolf Theatre Company: Known for producing innovative and thought-provoking plays.
Joffrey Ballet: One of the leading ballet companies in the U.S., performing classical and contemporary works.
Chicago Theatre: A historic theater hosting a variety of performances, including Broadway shows, concerts, and comedy acts.
Q: I know sports are big in Chicago. What are some must-see teams/games?
A: Chicago is passionate about sports, and attending a game can be a thrilling experience. Some must-see teams include:
Chicago Cubs (MLB baseball) at Wrigley Field: One of the oldest and most iconic baseball stadiums.
Chicago White Sox (MLB baseball) at Guaranteed Rate Field: Known for its energetic atmosphere.
Chicago Bulls (NBA basketball) at the United Center: The team has a storied history, and the atmosphere during games is electric.
Chicago Bears (NFL football) at Soldier Field: Watching a Bears game in this historic stadium is a quintessential Chicago experience.
Q: Any off-the-beaten-path areas to explore or unique experiences in the Chicago area?
A: If you’re looking to explore beyond the typical tourist spots, consider:
Pilsen: A vibrant neighborhood known for its colorful street art and diverse Latin American culture.
Andersonville: A charming neighborhood with unique shops, Swedish heritage, and a thriving LGBTQ+ community.
Garfield Park Conservatory: A stunning botanical garden featuring a wide variety of plants and art installations.
The 606 Trail: A converted elevated railroad track that has become a popular pedestrian and cycling path, offering great views of the city.
Q: Let’s talk food! What are the best eats in Chicago? Must-visit restaurants? Must-eat dishes?
A: Chicago is a food lover’s paradise. Some must-visit restaurants and must-eat dishes include:
Deep-dish pizza: Lou Malnati’s, Bacino’s, or Pequod’s are popular choices.
Chicago-style hot dogs: Portillo’s or Superdawg Drive-In are iconic spots.
Italian beef sandwiches: Al’s Beef or Mr. Beef are renowned for this local specialty.
Garrett Popcorn: Get a taste of the famous Chicago mix, a blend of caramel and cheese popcorn.
Gourmet burgers: Au Cheval or Kuma’s Corner serve delicious, indulgent burgers.
Q: What are some of the best spots to get drinks in Chicago?
A: Chicago has a thriving bar scene with a wide range of options. Some notable spots for drinks include:
The Violet Hour: A speakeasy-style cocktail bar known for its creative and well-crafted drinks.
The Aviary: A molecular mixology bar offering unique and innovative cocktail experiences.
Three Dots and a Dash: A tiki bar with tropical-inspired drinks and a lively atmosphere.
The Signature Lounge: Located on the 96th floor of the John Hancock Center, it offers stunning views of the city skyline while enjoying a drink.
Q: Any other must-do or must-know tips for visiting Chicago? Anything additional you’d like to share?
A: Chicago is a pedestrian-friendly city, so make sure to explore on foot and take advantage of public transportation.
Consider purchasing the Chicago CityPASS or Go Chicago Card to save money on popular attractions.
Check out the Chicago Cultural Center for free art exhibits, concerts, and events.
Chicago is known for its unpredictable weather, so it’s a good idea to pack layers and be prepared for changes! Also, don’t forget to try some Chicago-style popcorn at Garrett’s – makes for a tasty souvenir!
You can follow Amy Boyle on Substack here.