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Best of Chicago

Taste the Windy City’s cutting-edge cuisine and explore the Obamas' neighborhood.

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Rating: 5 out of 5 by EveryTrail members
Difficulty: Easy
Duration: Multiple days

Overview :  Chicago feeds on extremes, and on its own uncanny knack for reinvention—a trait that likely began with the Great Fire of 1871, which... more »

Tips:  Chicago has an extreme climate—from hot and humid in summer to freezing and windy in winter. It’s best to visit during late spring or ... more »

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Points of Interest

At the forefront of the groundbreaking molecular gastronomy movement, Alinea offers meals that are quite simply unlike any others. Dedicated followers eagerly await chef Grant Achatz’s scrupulously deconstructed innovations, which are always as delicious as they are surprising: venison is served atop a pillow of scented air; tiny spheres explode... More

2. Blake

Eleven months out of the year, this unassuming River North storefront goes unadorned, with no signage, no merchandise displays and a hard-to-find entrance that requires visitors to be buzzed in. Behind its white wall, however, a legendary high-end boutique awaits the city’s most cutting-edge fashionistas. Stylish customers are thrilled by Blake’s ... More

Specialing in Poblano food, this family-owned café is all about authentic flavors. In fact, the owner often travels to Mexico in order to obtain fresh, quality ingredients, and all of the restaurant’s salsa are homemade using a family recipe. Patrons frequently indulge in made-from-scratch specialties like the taco arabes, stuffed with... More

The Great Chicago Fire, street food, architecture, dance, Millennium Park, Greektown, baseball, Lincoln Zoo—whatever Chi-Town topic you’d love to learn more about, the Chicago Greeter program has you covered. A service of the Chicago Office of Tourism and Culture, this program offers customizable Greeter tours (pre-registration required) as well... More

Sailing on either Chicago River or Lake Michigan, the educational boat tours offered by Chicago Line Cruises are some of the city’s most popular sightseeing opportunities. Whether you’re a newcomer or local, the company’s knowledgeable guides provide 90 minutes of informative facts about the Windy City. The architectural cruise is hailed as one of... More

6. Ikram

Located on East Huron Street in a bright red building, this upscale women’s boutique is owned by Ikram Goldman, who at one time acted as Michelle Obama’s unofficial style consultant (not that you would ever get her to admit as much in print). The shop’s polished floors reflect mannequins showcasing everything from clothing to jewelry to... More

This hip Windy City café is another big supporter of fresh ingredients from regional markets and farmers. There’s always a "griddle cake" on the menu, but the ingredients change according to season and whim. In winter, they might be paired with stone fruit preserves, candied pumpkin seeds and maple sabayon; as summer arrives in the Heartland, you ... More

A 198-room European-style hotel on historic Water Tower Square, looking out on Lake Michigan and the Museum of Contemporary Art. Art Gallery Highlight: Gerhard Richter’s 27-foot Piazza del Duomo, Milan. Pop into the hotel’s restaurant, NoMI, for equally artistic fare.

800 N. Michigan Ave.
Chicago, Illinois
United States

(312) 335... More

With more than 260,000 works of art ranging from ancient Egyptian to contemporary, the Art Institute is home to some of the world’s most celebrated masterpieces. But don’t rush inside without viewing one of its most famous sculptures at the entranceway—the North and South Lions. Designed by Edward Kemeys, the lions have stood guard since 1894; the... More

Opened in April 2006, The James marries a residential vibe to a hotel setting. To evoke an apartment style, all of the 297 contemporary rooms have a separate dining area with plasma screen TV’s; some include a separate living area with oversize couches, coffee tables, and Eames chairs. Art is also an essential part of the property—the lobby... More

As you walk into the Peninsula, the concierge and receptionist greet you by name; classical music plays when you enter one of the 339 rooms; and your bedside table has a control panel to manage the lighting, deactivate the doorbell for privacy, and alert housekeeping when you want service. The luxury extends to the hotel’s spa by ESPA: it includes... More

The hipster BYO nook with four communal tables sits in an Avondale strip mall between a laundromat and a dry cleaner owned by relatives of Korean- American chef Bill Kim. Asian street food? Yes, but as interpreted by a chef who spent years working under the likes of Charlie Trotter and David Bouley. Whether ethereal squash pockets laced with... More