The Insider's Guide to Chicago
Situated on the shores of beautiful Lake Michigan, Chicago is the premier metropolitan destination in the Midwest. World-class restaurants, high-end shopping, lively nightlife, and globally recognized art and architecture make the Windy City a desirable weekend destination for a wide variety of travel personalities. With long winters that can border on brutal, spring, summer, and fall are the best times to see the city, so if it’s on your list for an upcoming trip, keep scrolling for our picks of where to eat, drink, stay, and play.
Who: Public Hotel
What: Located in the historic Gold Coast district, this Ian Schrager–designed space is an ideal combination of classic elements and sleek contemporary accents. Chic public spaces include a coffee bar, library, and screening room. The well-appointed rooms feature Frette linens.
Who: The Violet Hour
What: A recipient of the James Beard Foundation's 2015 award for outstanding bar program, this stylish lounge is where to go for fantastic cocktails in a sophisticated environment. The lounge’s exterior features a constantly changing hand-painted mural, and a lack of signage means you have to look out for the singular lightbulb to find the hidden entrance.
Who: The Aviary
What: A specialty cocktail lounge from award-winning chef Grant Achatz, The Aviary takes cocktails more seriously than anywhere else you may have ever been. The bartenders are trained as chefs, and the cocktails are created in a drink kitchen. Consider ordering one of the three- or five-course packages for a full sampling of The Aviary’s capabilities.
Who: Lou Malnati’s
What: The destination for original Chicago-style deep-dish pizza, Lou Malnati’s is a Chicago institution. There are several locations of the iconic restaurant around the city, so you’ll never be too far from the gooey deliciousness. Make sure to get the Buttercrust; you won’t be sorry.
Who: Pump Room
What: Located in the Public Hotel, this chic eatery is the perfect spot for a romantic dinner or stylish weekend brunch. A Chicago institution, the pump room was recently renovated and redesigned, but walls of black-and-white photos from the restaurant’s heyday recall its rich history.
What: With over 77,000 works including significant pieces like Georges Seurat's "A Sunday on the Isle of La Grande Jatte," Grant Wood's "American Gothic," and Edward Hopper's "Nighthawks," this is an international art-world destination.
Who: Luxury Garage Sale
What: High-end designer pieces at consignment prices make for a fun place to stop when in the city’s trendy Old Town neighborhood. Score new or gently used designer clothing and accessories while browsing the stylish, glamorous boutique.
What are your favorite spots in Chicago? Share where you always visit in the comments below!