Chicago City Guide
Outside of Washington, DC, the city I’ve spent the most time in is CHICAGO. At one point in my career, I was averaging about one week a month in the Windy City, so over the years I’ve had time to explore the various neighborhoods and I learned to appreciate the second city’s diversity. Of course the best time to visit Chicago is the spring to fall because winters are bitterly cold.
For fashionistas, there’s must-do shopping at Barney’s, Blake, Eataly, Sophia, and of course Ikram. For art + design enthusiasts, you’ll want to visit Agent Gallery, Branca, Elements, Greer, Jayson Home + Garden, Kara Mann, Pavilion Antiques, P.O.S.H., Salvage One, Scout and Wright.
1300 S. Lake Shore
To infinity and beyond! I’ve never met a planetarium I didn’t like, Adler is fun!
Architecture Cruises and Tours
Unique ways to see + learn about Chicago’s iconic architecture like the Aqua Tower, Merchandise Mart, Tribune Tower and even the 1893 World’s Fair.
159 E. Monroe Street
One of the country’s best art museums with a stellar collection of Contemporary, European and Impressionist art.
1400 S. Lake Shore
From DNA to dinosaurs, one of the world’s largest natural history museums.
201 E. Randolph Street
No visit to Chi-town is complete without seeing Cloud Gate (aka Lima Bean).
5757 S. Woodlawn
At the University of Chicago, this prairie-style home was designed by architect Frank Lloyd Wright in 1910.
Chicago’s food scene is popping, so be sure to make reservations weeks in advance.
1723 N. Halsted
Go with no pre-conceived ideas and Grant Achatz will amaze and wow you.
615 W. Randolph
A cool wine bar serving delicious Mediterranean tapas.
1633 N. Halsted
Modern Italian cuisine with delicious wood-fired pizzas. Also try the Tagliolini Nero.
1400 W. Randolph
An incredible Korean BBQ adventure. Grab a seat at one of the grill tables and watch the magic happen.
720 N. Wells
American comfort food + stellar wine list makes Alpana Singh’s “house” a hot spot.
1729 N. Halsted
American seasonal specialities created by award-winning chef Lee Wolen.
2957 Diversity Avenue
Buzzing Chinese-Portuguese fusion restaurant with a hippie vibe.
445 N. Clark
Not a huge fan of Mexican cuisine? Rick Bayless will make you a believer.
Girl + The Goat
809 W. Randolph
Chef Stephanie Izard’s rustic Mediterranean nose-to-tail foodie favorite.
GT Fish + Oyster
531 N. Wells
Some of the city’s best oysters and seafood is served at this hotspot.
2651 W. Peterson
On the North Side, one of Chi-town’s best sushi restaurants.
2300 N. Lincoln
A special occasion restaurant when only the best will do.
868 N. Franklin
An Chicago institution with a sleek setting serving seasonal American cuisine.
1466 N. Ashland
Creative global cuisine at this Wicker Park hotspot. Only 26 seats.
845 W. Fulton Market
A modern + sophisticated gastropub. Try the house-made pork rinds.
676 N. Saint Clair
I’m partial to TRU because my Hubby and I had our first date here, but the food is always exquisite and the service exceptional.
Always make reservations directly with the hotel to take advantage of the best deals.
21 E. Bellevue
Luxury industrial chic in the Gold Coast with the popular Italian seafood restaurant Nico Osteria.
120 E. Delaware Place
Beautiful rooms, beautiful service and beautiful views of Lake Michigan.
1301 N. Parkway
The modern + chic no frills Ian Schrager property in the Gold Coast.
330 N. Wabash
Urban sophistication atop a Mies van der Rohe building near popular attractions.
108 E. Superior Street
One of Chicago’s best. Luxury, timeless elegance and outstanding service.
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