June 5-8 Trip suggestions

Question

We have a group of 4 adults looking to go to Chicago for a long weekend in June. Looking for the best areas to stay and recommendations on things to do.

Tunings we enjoy: food, drinking, baseball, great views, water, live music, and open to any must see and do during our first trip to the city.

Answer

Chicago is a fantastic destination for a long weekend, and with your group’s interests in food, drinking, baseball, great views, live music, and water, you're in for a great time. Here's a guide to help you make the most of your trip:

Best Areas to Stay in Chicago:

River North: This is one of the best neighborhoods for first-time visitors, with easy access to top restaurants, bars, and attractions. It’s vibrant and centrally located, making it easy to walk to many of the city’s must-see sights like the Magnificent Mile, Millennium Park, and Navy Pier. Plus, you’ll find a wide range of hotels, from boutique to luxury.
The Loop: If you’re looking to be close to the city’s iconic landmarks like Grant Park, the Art Institute, and the Chicago Theatre, the Loop is a great option. The area has a mix of business and leisure, with plenty of dining options and a good connection to public transportation.
Lakeview (Wrigleyville): If you're a baseball fan, staying in Lakeview puts you right near Wrigley Field, home of the Chicago Cubs. This neighborhood has a laid-back vibe, with plenty of bars, restaurants, and things to do. It’s perfect for enjoying Chicago's nightlife and catching a game if the Cubs are in town.
West Loop: Known for its trendy dining scene, West Loop offers plenty of upscale and unique restaurants, great bars, and a lively atmosphere. If food is a top priority, you’ll love this neighborhood. It’s a bit further from the main tourist sites but still well-connected to the rest of the city.

Things to Do:

1. Food and Drinking:

Deep Dish Pizza: You can’t go to Chicago without trying deep dish pizza. Popular spots include Giordano’s, Lou Malnati’s, and Pequod’s. For something unique, try Art of Pizza for a custom deep dish experience.
Chicago Food Tours: Consider doing a food tour to get a taste of the best local eats. There are walking tours available in neighborhoods like the West Loop and River North, or you can even explore Chicago’s famous food halls like the Time Out Market.
Craft Breweries: Chicago is home to a thriving craft beer scene. Check out local breweries like Revolution Brewing, Lagunitas, and Goose Island for a great selection of brews.
Rooftop Bars: For fantastic views and drinks, head to one of Chicago’s popular rooftop bars. Some top spots include the Roof at the Wit Hotel, Cindy’s Rooftop, and LondonHouse’s rooftop bar, offering stunning views of the skyline and the Chicago River.

2. Baseball:

Wrigley Field: If you’re in town during baseball season, try to catch a game at Wrigley Field, one of the oldest and most iconic ballparks in the country. It’s located in Lakeview, and the surrounding area has plenty of bars and restaurants perfect for pre- or post-game drinks.
Guaranteed Rate Field: If you’re a White Sox fan, head to the South Side to visit Guaranteed Rate Field for a game. It’s less touristy than Wrigley, but it offers a more local experience.

3. Great Views and Water:

Navy Pier: Navy Pier is a must-see for first-time visitors. You can take a ride on the Centennial Wheel, enjoy a variety of attractions, and walk along the waterfront. There are also great restaurants and bars, and you’ll have beautiful views of Lake Michigan.
Chicago Riverwalk: A walk along the Chicago Riverwalk is a great way to enjoy the city’s architecture and water views. You can rent bikes or take a boat tour to see the city from a different perspective.
Skydeck Chicago or 360 Chicago: For incredible views of the city, visit one of the observation decks like the Skydeck at Willis Tower (formerly Sears Tower) or the 360 Chicago at the John Hancock Center. Both offer sweeping views of the city and Lake Michigan.

4. Live Music:

The Green Mill Cocktail Lounge: For an iconic Chicago jazz experience, visit the Green Mill. It’s been around since the 1900s and still hosts great live jazz performances in an intimate setting.
Lincoln Hall: If you’re into indie and live music venues, Lincoln Hall in Lincoln Park is one of the best spots to catch local and touring acts.
Buddy Guy’s Legends: A Chicago institution for blues music, Buddy Guy’s Legends offers live performances every night. It’s a must-visit for anyone who loves great live music and a lively atmosphere.

5. Must-See Attractions:

Millennium Park and Cloud Gate (The Bean): This iconic park is home to the famous Cloud Gate sculpture, also known as “The Bean.” It’s a great spot for photos and a nice place to relax and enjoy the outdoors in the city.
Art Institute of Chicago: One of the oldest and largest art museums in the country, the Art Institute is a must for art lovers. It’s home to world-class collections, including works by Picasso, Grant Wood, and Van Gogh.
Architecture Tour: Chicago is known for its unique architecture, and one of the best ways to see it is by taking a Chicago Architecture River Cruise. You’ll get to learn about the history and design of the city’s iconic buildings while enjoying a boat ride along the Chicago River.

Summary: Chicago has so much to offer, from incredible food to stunning views and a vibrant live music scene. Based on your interests, staying in River North or the West Loop would give you great access to food, bars, and attractions. Be sure to check out Wrigley Field if you're a baseball fan, and take time to enjoy the water views along Navy Pier or the Riverwalk. With so much to do and see, you’ll have an unforgettable long weekend in Chicago!

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