Chicago City Guide

chicagoOutside 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, EatalySophia, and of course Ikram. For art + design enthusiasts, you’ll want to visit Agent GalleryBranca, Elements, Greer, Jayson Home + Garden, Kara MannPavilion Antiques, P.O.S.H., Salvage OneScout and Wright.

cloud gate
The Chicago waterfront is to-die-for, so don’t miss a walk or jog along Lake Michigan.

Adler Planetarium
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.

Art Institute
159 E. Monroe Street

One of the country’s best art museums with a stellar collection of Contemporary, European and Impressionist art.

Field Museum
1400 S. Lake Shore

From DNA to dinosaurs, one of the world’s largest natural history museums.

Millennium Park
201 E. Randolph Street

No visit to Chi-town is complete without seeing Cloud Gate (aka Lima Bean).

Robie House
5757 S. Woodlawn

At the University of Chicago, this prairie-style home was designed by architect Frank Lloyd Wright in 1910.

alinea hot potato

Alinea’s famed Hot Potato

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.

Belly Q
1400 W. Randolph

An incredible Korean BBQ adventure. Grab a seat at one of the grill tables and watch the magic happen.

Boarding House
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.

Fat Rice
2957 Diversity Avenue

Buzzing Chinese-Portuguese fusion restaurant with a hippie vibe.

Frontera Grill
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.

The Publican
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. 

The Thompson
21 E. Bellevue

Luxury industrial chic in the Gold Coast with the popular Italian seafood restaurant Nico Osteria.

Four Seasons
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.

The Langham
330 N. Wabash

Urban sophistication atop a Mies van der Rohe building near popular attractions.

The Peninsula
108 E. Superior Street

One of Chicago’s best. Luxury, timeless elegance and outstanding service.

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