Chicago is one of the most scenic cities I’ve ever traveled to. The skyline is said to rival New York City’s, dotted with iconic landmarks like the Wrigley Building, Tribune Tower, and John Hancock Building. With the Chicago River running through the city, there is a subtle European charm with every bridge you pass. Chicago has dozens of neighborhoods to explore from the hipster mecca Wicker Park to the picturesque Lake Shore Drive neighborhood. While we recommend visiting this cultural hub during the warmer months (hi, Lollapalooza), there is something beautiful about a fall getaway (everyone looks cuter in autumnal garb). No matter what month you decide to travel, below you will find a complete weekend guide to Chicago.
Where to Stay:
Unless you are a keen Chicago explorer, we suggest choosing a super chic hotel in the heart of the city’s must-see spots. The stunning Kimpton Gray Chicago is located near Grant Park, right off the Blue Line subway route, and is walking distance to several coffee shops, restaurants, and great shopping. Kimpton hotels are notoriously eclectic, dog-friendly, and social. This property is no exception. The entrance is marble and grand while the rooms are warm and uniquely designed. Be sure to stop by the daily social hour in the lobby where guests are encouraged to mingle with a cocktail.
For something even more upscale but still in the heart of downtown Chicago, opt for the Ritz-Carlton, Chicago. The lobby alone will leave you speechless, with stunning marble floor and sophisticated decor. The rooms all boast stunning views of Chicago’s Navy Pier, Lake Michigan, and other notable Chicago sights.
Where to Drink:
Whether you are staying at the Kimpton Gray Chicago or not, Boleo is a vibrant rooftop bar that is totally worth checking out. On the weekends, Boleo almost always offers live music as the backdrop to colorful craft cocktails being poured until the wee hours of the night.
For a more subdued atmosphere, head over to the Cherry Circle Room located inside the iconic Chicago Athletic Association. Enjoy a fine dining experience in a swanky reimagined space, or grab a seat at the sophisticated bar and savor a beautiful cocktail.
If you’re staying at the Ritz-Carlton, Chicago, a great place for a nightcap is the hotel’s Rooftop at Torali restaurant. The space overlooks the Magnificent Mile, a premier shopping destination for tourists, and serves as a worthy cocktail lounge.
What to Do:
The cultural ambiance in Chicago ranges across quite an expansive spectrum. Depending on your preferences, you can savor an indulgent food tour of the city, spend the day perusing museums, or head to a live concert at one of the many iconic venues in the city. We recommend checking out the Chicago Cultural Center for a peak at the evolving exhibitions, and the largest Tiffany glass dome in the world, clocking in at 38 feet in diameter and made of Tiffany Favrile glass. It is gorgeous.
In the evening, you can check out one of the oldest jazz clubs in Chicago, the Jazz Showcase. Since opening in 1947 this venue has hosted unmissable musicians, and recently relocated to a chic South Loop space.