Cities We Love: Chicago
Chicago is my hometown and though I’ve been away for more than 14 years now, it will always be my home.
As I am writing this, the current temperature in Chicago is 16F while it is 42F in Atlanta.
There’s a reason I don’t live there anymore!
But Chicago is an incredible city, and during certain times of the year, it’s the best city in the US (in my biased opinion). Chicagoans live for summertime, enduring long and cold winters for the 3-4 months of summer weather that turns Chicago into an amazing city. Now that I live in the South, I opt for visits to my hometown between June and August when it is super hot and humid in Atlanta and absolutely beautiful in Chicago.
And while you could visit Chicago year-round, I’d highly recommend visiting during late Spring into early Fall. Not only will the weather be at its best, you will also have access to so many things to do around the city and you will also likely fall in love with The Windy City.
World-Class Arts & Culture
Explore the renowned Art Institute of Chicago or my personal favorite, the Museum of Contemporary Art. Catch a Broadway-caliber performance at one of the city's iconic theaters, or immerse yourself in live jazz at an intimate club. There are live music venues, big and small, scattered throughout the city making it an ideal city to catch a show with your favorite artist or discover someone new.
Culinary Excellence
If you’ve watched The Bear, you are somewhat familiar with Chicago’s culinary scene. The show features some of the city’s most famous restaurants, chefs, and local delicacies - whether $$$$ or more affordable. We can help you plan your stay to check out some of the best Chicago has to offer from fine dining to hot dogs and deep dish (our personal favorites). And there are amazing bars with craft cocktails and skyline views or cozy beer gardens with a range of local and craft beers on tap.
Luxurious Stays
There are so many wonderful hotel options in Chicago that it can be hard to choose the perfect stay for your trip. Let us help you find the right hotel for you - ideal location, luxurious amenities, and panoramic city views that will make you feel like you’re on top of the world. For the ultimate luxury experience (and incredible spa), stay at The Peninsula Chicago. Or stay across from Chicago’s Millennium Park and enjoy lakefront views at the Chicago Athletic Association.
Outdoor Adventures
Chicago’s location on Lake Michigan is what makes it so incredible in the summertime (and so cold in the winter). You’ll find beachgoers, volleyball players, joggers, bikers, festivalgoers, and more all along the beaches. Don’t forget Chicago’s other body of water, the Chicago River: stroll the scenic Chicago Riverwalk and take an architectural boat tour. If sports are more your thing, don’t miss seeing a baseball game while you’re in town!
Unique Neighborhoods
I always recommend that visitors to Chicago get out of downtown and into the neighborhoods. Take the El and travel west to Wicker Park or Logan Square to browse unique boutiques and dine in some of the city’s best restaurants. Travel north on the Brown or Red Line to iconic neighborhoods - Lincoln Park, Lakeview, Wrigleyville, or Old Town. You’ll find plenty to do throughout each of these areas whether it’s food, drink, sports, or comedy at Second City.
In the Summer, you will find local festivals happening every weekend across the city with live music and locals enjoying the beautiful weather. This is a great way to see more of the city and experience the neighborhoods at their best.
Planning a long-weekend in Chicago and need some expert advice? Let us help you find the perfect hotel and craft a custom itinerary that will make you fall in love with the city!