While I might be a little biased, having spent the last four years of my life in the Northwest Suburbs of Chicago, I think Chicago is the best city in the world. The Windy City, is a vibrant metropolis with a rich history, diverse culture, and endless things to do. While it’s an amazing city to visit year-round, I must admit that the winters, though brutal, have their own unique charm. Here’s how you can make the most of a weekend in Chicago, no matter the season.
Where to Stay
As an avid traveler myself, I’m always looking for great hotel options that offer convenience, comfort, and unique experiences. Chicago has an array of fantastic hotels, especially through brands like Bonvoy and Hyatt. Here are some of my favorites:
- The Renaissance (Bonvoy): This hotel sits right on the Chicago River, offering stunning views and easy access to the theatre district. It’s an ideal spot for anyone looking to enjoy a weekend filled with arts, culture, and great food.
- The Gwen (Bonvoy): One of my personal favorites, The Gwen offers unbeatable value for its prime location and excellent accommodations. The lobby’s free coffee is a nice touch, and the champagne vending machine adds a fun, quirky perk. Its location near Michigan Avenue also makes it a great base for those visiting during the Christmas Parade season.
- JW Marriott: While a bit further from Michigan Avenue, the JW Marriott is conveniently located near the theatre district and numerous attractions in the Loop. It was the perfect place for my family the night before the Chicago Marathon.
- The Grand Hyatt: Another hotel my family has enjoyed multiple times, the Grand Hyatt is a wonderful option whether you’re attending an event or just exploring the city. It’s an excellent choice for marathoners and spectators alike, with its convenient location near the starting line of the Chicago Marathon.
- The Palmer House: A true classic Chicago hotel, the Palmer House boasts an old-school charm with large guest rooms (though some bathrooms can be on the smaller side). The hotel’s dining options are a big perk, offering excellent meals right on-site.
Chicago’s Must-See Attractions
There’s no shortage of things to do in Chicago, whether you’re interested in history, culture, sports, or just soaking in the sights. Here are a few highlights from my family’s favorite attractions:
- Architectural Boat Tour: Without a doubt, this is my top recommendation. Whether you’re cruising along the river on a beautiful summer day or catching the sunset, this tour is the perfect way to take in Chicago’s stunning architecture while learning about its fascinating history.
- Chicago Sports: Sports are a big deal in Chicago, and my family loves cheering on our local teams. From the Cubs and White Sox for baseball fans to the Blackhawks, Bulls, and Bears for hockey, basketball, and football, Chicago’s sports scene offers something for everyone.
- Chicago Theatre: A night out in Chicago wouldn’t be complete without experiencing its world-class theatre scene. My husband and I enjoy a lovely dinner followed by a show at one of Chicago’s many theaters, and I can confidently say that Chicago’s theatre offerings rival those in New York, London, and beyond. Whether you’re into musicals, comedy, or drama, there’s always a great performance to catch.
- Food: Chicago is a foodie’s paradise. While it’s hard to narrow it down, a few family favorites include the iconic Lou Malnati’s pizza, Hampton Social for a laid-back vibe, The Smith for a fun brunch, Joe’s Seafood for a treat, and of course, Firecakes. If you know, you know about Firecakes—trust me, it’s a must-try!
Museums, Museums, Museums
Chicago is home to an incredible collection of museums that are perfect for a weekend of exploration. The city’s museums rank among the best in the world, with options for all ages. Some of our family favorites include:
- The Museum of Science and Industry (Now known as the Griffin Museum of Science and Industry): This museum is hands-on and engaging, making it perfect for kids and adults alike. It’s one of the largest science museums in the world, offering tons of interactive exhibits and fun learning experiences.
- The Field Museum: Whether you’re fascinated by dinosaurs or the wonders of human history, the Field Museum offers an immersive experience for visitors of all ages.
- The Children’s Museum at Navy Pier: If you’re traveling with little ones, this museum is a must-see. It’s interactive, fun, and educational, making it a great stop for families.
Chicago’s museum scene rivals that of other major cities like Washington, D.C., and Paris, and there’s so much to explore, from art to history to science.
The Bottom Line
While Kingdom and Cruise Travel is well-known for our expertise in planning Disney, Universal, cruises, and all-inclusive vacations, I don’t want you to miss out on working with me or one of my wonderful colleagues to plan your domestic travels. Whether for business or leisure, our team of travel professionals is here to help you plan your next trip—no matter where in the world you’re headed. And the best part? With partnerships with top suppliers like Marriott, Hyatt, Hilton, and Expedia, we’re ready to make your next trip hassle-free and memorable.
So, pack your bags and get ready to explore Chicago—the Windy City awaits!