Stuff to Do in Chicago

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While You’re in Chicago, You Oughtta Enjoy One of the World’s Great Cities!

If you’re coming for a 4-Man Intensive, a consultation, Roundtable meeting or seminar, you should stick around for an extra day or two and relish one of the great cities of the world.

Chicago holds its own with New York, San Francisco, Paris, London, Hong Kong, Dubai and Shanghai. (In many respects it’s even superior to Calcutta.) Ha. Seriously, you could stay a week and only scratch the surface.

Some of my favorite places in Chi-Town:

The Magnificent Mile is the jewel of downtown Chicago. There, you can check out the Hancock building (5 states are visible on a clear day), the elite Watertower Place mall, the Apple store, world-class shopping at places like Sak’s Fifth Avenue. Tons of restaurants too.

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Lake Michigan is gorgeous, especially in the summer, and its beaches are the site of biking, volleyball, rollerblading, swimming, soccer, baseball and sunbathing.

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The El Train takes you almost anywhere in Chicago to almost anywhere else. Multilple lines run from downtown to Midway and O’Hare airports, north to Evanston, west to Oak Park and Forest Park, and south. The Metra Train is the suburban line that goes to the far edges of the suburbs as well as Northwest Indiana.

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Navy Pier is a military installation turned shopping mall and eatery, jutting into Lake Michigan. In summertime they have fireworks several nights at week at 10pm. Enjoy the ferris wheel and the IMAX theater.

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Millennium Park is famous for “the bean,” Pritzker Pavillion which is an outdoor concert hall, and Crown Fountain which changes colors all day long. Grant Park is home of the Chicago Jazz Festival and the Chicago Blues Festival.

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The Neofuturists are not known to most tourists, but is Chicago’s longest-running theater production. “30 plays in 60 minutes.” It’s odd, offbeat, ideal entertainment for college students and weirdos of all stripes. In the 2nd floor of a mortuary in Andersonville on the North Side.

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Tons of GREAT Theaters: Almost any night of the week, these theaters are delivering world-class performances: Looking Glass, Goodman, Bank of America, Oriental, Congress.

You can always get a rundown of Chicago entertainment – bands, movies, theater performances, poetry readings and eateries at

The Chicago Architecture Boat Tour surveys the city from the Chicago River and Lake Michigan. Chicago has one of the most beautiful skylines of any city in the world and whether you go day or night, it’s breathtaking.

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Second City is the comedy club that gave birth to John Belushi, Chevy Chase, John Candy, Tina Fey and Alan Alda. Delivers hilarious performances nightly.

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The Field Museum of Natural History, the Museum of Science and Industry, Adler Planetarium and Shedd Aquarium are all within a few miles of each other, all fabulous.

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Blues Clubs: My favorites are Kingston Mines and Buddy Guy’s legends. House of Blues has all kinds of acts.

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Fitzgerald’s Night Club in Berwyn is known as “The best roadhouse north of Texas.” Rockabilly, Rock, Country and Jazz.

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The Chicago Symphony Orchestra keeps a full schedule right in the middle of downtown. It’s across the street from the Art Institute of Chicago.

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Willis Tower is Chicago’s most famous building. On the south end of downtown, will not disappoint you on a clear day.

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Soldier Field and Wrigley Field are home to the Bears and the Cubs. A summer evening in Wrigley is the best time & place to drink a beer. They have plenty of it, too.

I LOVE Chicago. Moved here almost 20 years ago from Nebraska to take an engineering job. People ask why I still live here, when we could just as easily live just about anywhere else.

About 7-8 years ago it occurred to us, we could move away if we wanted to. Why didn’t we escape the winters? If you don’t have a commute every day, it’s as good as any world class city. A Nebraska boy can deal with 4 months of winter and the rest of the year it’s super.

We have fabulous food (we’re incredibly spoiled here, actually), we have Broadway-level shows almost every night of the week, and every great band and entertainer always makes a stop in Chicago.

With Midway airport I’m 6 hours away from any city in the US and with O’Hare I’m 24 hours from any city in the world. Yet it’s friendly and midwestern. You don’t get an “east coast attitude” from Chicagoans.

I hope you have an unforgettable time in our fantastic city!

Perry Marshall

P.S.: Some of my favorite restaurants: India House; Sushi Samba; Giordano’s Pizza; Arun’s Thai Restaurant; Fogo de Chao Brazilian Churrascuria. Pegasus in Greektown; Spring World in ChinaTown, with cuisine from the Yunnan province near Tibet.

Restaurant recommendations from my staff:

Danielle: The Kerryman Irish Bar & Restaurant

Sam: For pizza – Lou Malnati’s, For an EPIC reuben sandwich – Manny’s Deli (Oh baby, baby), For the best italian beef known to mankind – Johnnie’s Beef, For hot dogs – …I would have said the Sinai Kosher factory, but they closed that monument to perfection down. =( I am deeply grieved.

Jeremy: The Bongo Room – Great place for incredible breakfast and lunch, Signature Room Restaurant – Very pricey restaurant on the 95th floor of the John Hancock building, but so worth it for the food and the incredible views of the city. This is where I proposed!

Sue: Would recommend Carnivale on Fulton–great place to go for a party (noisy) atmosphere–feels like it’s a cruise ship. Crowded on weekends–need a reservation. Great Mojitos (I like the raspberry Mojito w/o rum). Maggiano’s downtown (be sure to have the Maggiano’s salad with the bits of toasted prosciutto and blue cheese dresssing), Petterino’s, and the Atwood Grill (fabulous and pricey). And on Rush Street–Gibson’s for steak. Gibson’s is always crowded, no matter what day–always need a reservation, and you still will have to wait in the bar. The waiter brings the enormous raw cuts of beef to the table on a tray before you order. Every portion is super-sized, so you could share any steak or side dish on the a la carte menu with 1 or 2 others. Fabulous creamed spinach. Twice-baked potatoes superb. Large portion desserts–but you won’t have room for any. All of these restaurants are “expensive to very expensive.” But for the ultimate dining experience, both gastronomically and financially speaking, book a table at Everest, which is just south of the Loop in the Chicago Stock Exchange building which extends over Congress Parkway. Alpana Singh of the TV program Check Please used to be their wine steward. The only time I ate there was for an anniversary about 10 years ago, and I still remember the dessert–the best dessert I ever had. It was maple mushroom ice cream. It was beyond fabulous. Who would think those ingredients (along with some chef-made candied toppings) would be that memorable and that delicious together. Dining at Everest is about a 2-hour experience. It’s the evening’s entertainment.

Lorena: Reza’s Restaurant, Maya Del Sol in Oak Park, Marcello’s Lincoln Park

Tiffany: Bandera Restaurant, Ron Of Japan, Ed Debevic’s

What’s your favorite thing to do in Chicago? Your comments are welcome….

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About the Author

Perry Marshall has launched two revolutions in sales and marketing. In Pay-Per-Click advertising, he pioneered best practices and wrote the world's best selling book on Google advertising. And he's driven the 80/20 Principle deeper than any other author, creating a new movement in business.

He is referenced across the Internet and by Harvard Business Review, The New York Times, INC and Forbes Magazine.

4 Comments on “Stuff to Do in Chicago”

  1. Not sure if I could handle living in Chicago (from just north of Fort Wayne IN) but have talked about weekend trips to it many times.

    Thank you for a great intro to Chicago, many of the areas you mentioned I had no clue of.

    Take care,

  2. Don’t forget the Art Institute. World class photo exhibits downstairs, the amazing Thorne Miniature Rooms collection, Matisse, Monet, Picasso, Renoir, Seurat, Van Gogh and many other important painters. A visit to the Art Institute is always the highlight of my trip.

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