Best of Chicago: A Local's Guide

The absolute best way to see the city is aboard one of the Chicago Architecture Foundation’s river cruises. Hear fascinating stories behind the buildings along the Chicago River and learn how Chicago grew into one of the world's largest cities in less than 100 years.

If you only have evenings free or if the river cruise is sold out, you can also cruise on Lake Michigan and enjoy the breathtaking Chicago skyline with the Chicago by Night Cruise.

Sip, savor and stroll along the new Chicago Riverwalk. Although the idea of a Riverwalk was included in Burnham’s 1909 Plan of Chicago, the first installment didn’t happen until the 1970s, and since 2011, the Chicago River has been transformed. The Riverwalk covers 1.25 miles through the heart of the city and provides easy access to enjoy Chicago’s waterfronts, architecture and seasonal pop-up restaurants, wine bars, and more.

The crown jewel of Millennium Park is not “the bean,” it’s really the Chicago Athletic Club Association Hotel. Even if you don’t stay there, it’s worth a stop on your trip. There is so much to explore under one roof and something for everyone. Dine at Cindy’s on the rooftop. Enjoy a classic cocktail at the former speakeasy, Milk Room, or take your group to the Game Room for shuffleboard, billiards and more.

Laugh your face off at The Second City, the legendary improv theatre that launched the careers of comedic royalty including Alan Alda, Bill Murray, Gilda Radner, John Candy, John Belushi, Dan Aykroyd, Eugene Levy, Catherine O'Hara, Chris Farley, Mike Myers, Steve Carell, Tina Fey, Amy Poehler, Stephen Colbert and many more.

Greektown:

You will hear ravings about the restaurants on Randolph Street, but the adjacent Greektown neighborhood is a standard for us locals. Greektown has the best sampling of Greek heritage outside of Athens. The small but mighty restaurant row features two essential favorites in Greek Islands and Athena. Pro tip: Greek Islands has FREE VALET PARKING.

Pizza:

Settle the great pizza debate! While you cannot go wrong with any of the top local chains of Lou Malnati’s, Gino’s East and Giordano’s, it is well known and accepted that Lou Malnati’s has the best crust and is the best of the bunch. Gino’s East has great thin crust options and specialty toppings (try the Diavolo) while Giordano’s has the most locations so it’s easy to find no matter what neighborhood you’re exploring.

• Lou Malnati’s

• Gino’s East

• Giordano’s

Steakhouse vs. Italian?

In Chicago, you don’t have to choose! Chicago is home to the Italian steakhouse. At these casual yet fine dining gems, you get both Italian and steakhouse menus combined for a literal feast. Gene & Georgetti and Chicago Chop House are two such gems. Go family-style so you can try as many dishes as possible.

Chinatown:

A short ride on the red line to Cermak/Chinatown will take you steps away from hundreds of restaurants and shops. Explore the older strip on South Wentworth Avenue for ice cream, bubble tea and bakeries. Then head over to the newer pavilion south of Archer Street for dinner at Ming Hin or Lao Sze Chuan.

Mexico en Chicago!

Mi Tierra - For a fun-filled, celebratory night out, consider venturing to Little Village neighborhood for this raucous restaurant with delicious cuisine, giant margaritas and a live mariachi band.