2008
This local’s perspective is by Miles Traer. Miles grew up in Chicago’s backyard and so knows the city through and through. He speaks knowledgably- and so passionately about his hometown that he has convinced me to put Chicago at the top of my ’short list’ of places to visit. Whether you prefer beer and baseball or fine cuisine and architecture, Miles has covered this city as only a local expert can. Enjoy!
1. Give 5 adjectives that you would use to describe the “feel” of Chicago and its residents.
Proud, enthusiastic, sarcastic, jovial, gregarious
2. What is your favorite neighborhood/area of Chicago?
There are so many niche neighborhoods in and around Chicago, but my personal favorite is Wrigleyville. It has everything you want in a Chicago neighborhood: great people, that 1920’s style architecture, great bars, and a ton of places to pick up a polish sausage and watch the baseball game. For something a little more unique to Chicago, check out Greek town. Some of the best hidden restaurants in the city are here.
3. Which cuisine do you think Chicago does best? What is the runner-up?
Chicago is home to some of the best food in the country. But if you had to pick a single style, it would have to be the steak house. Going all the way back to the time of the Union Stock Yards, Chicago has steak down to a true art form. There’s Morton’s Steak House for a fabulous atmosphere and a fantastic meal, or Gene and Georgetti’s for a classic Chicago meal – get the garbage salad! There are too many runner-ups, but I’d be remiss not mentioning Frontera Grill (best Mexican in the country), Pizzaria Uno (birthplace of deep-dish), and the Billy Goat Tavern (home of the cheezborger).
4. What is the best free thing to do?
Provided you can keep your wallet safely locked in your pocket, a walk down Michigan Avenue is the way to go. Otherwise, a walk along Lake Michigan during the summer with a stop by Buckingham Fountain is a beautiful way to spend a day.
5. What is your favorite type of entertainment?
There is nothing that compares to a baseball game during the day at Wrigley Field. After the game, run over to Second City and catch the late-night improv set.
6. List the best family friendly activity in Chicago.
A trip to any of the amazing museums in Chicago. For the kids, the Museum of Science and Industry is amazing – hands on, entertaining, and the coal mine exhibit still gets me.
7. What spot would you send a couple, looking for a romantic weekend?
A stay at the Drake Hotel in a room overlooking Lake Shore Drive is about as perfect a stay that I can imagine.
8. Describe a perfect day…one that captures what your area/city is all about. In 3 sentences or less.
The perfect day starts with a game at Wrigley Field. After that, take a cab over to the Chicago River and take the architecture cruise while catching some sun. Finish the day with dinner at any of the fantastic restaurants and a spin on the Ferris Wheel at Navy Pier.
9. Tell us about a place that you love to go, whether it is in the guidebooks or not.
The Art Institute of Chicago is an absolute must for anyone visiting for the time, and anyone living there for that matter. It houses the most impressive collection of art outside of the Met in the country.
A personal favorite that you won’t find in any guidebook is the midnight show of “Too Much Light Makes the Baby Go Blind” at the Neo-Futurarium (5153 N. Ashland). This is an improv comedy club that won’t kill the wallet the way the top shows at Second City might (just $7 plus $1 times the roll of a die). Hilarious.
Want to share, brag, or tell about your town? If so, send an e-mail or comment on this post–then you can be our next local expert!
Thanks to Laffy4K for the Chicago picture!














11 Responses
We’d be remiss if we didn’t mention the great theatre available to Chicago natives and tourists alike. Our family has seen Wicked, A Christmas Carol, and The Color Purple all in the last year here in Chicago. What a great city! — Family Travel Girl
Chicago sounds like a really great place to visit! I’d love to see Wrigley Field and the Drake Hotel and the improv club. :o)
@Family Travel Girl: great addition–i have been wanting to see Wicked for quite some time now. what are some of the best theaters there?
@Rhea: Miles definitely shared a wide range of options for a trip to Chicago–I want to check out the improv club as well..and am saving up for a stay at the Drake Hotel!
TMLMTBGB is awesome! But it is also in the Fromer’s Chicago guide book. A free pizza if the show is sold out!
Once you know the rhythm of the city, it is an absolute wonderful place to live.
The thing I found most impressive is that when you walk downtown and start looking up or around, invariably somebody will come up to you and ask you where you want to go. VERY friendly city.
The Chicago and the Oriental Theaters are beautiful, like going back in time into old Chicago. The architectural tour by boat down the Chicago river is a must, you drift past old and stunningly beautiful limestone buildings built in the rubble of old Chicago and over the scars of the great 1871 fire that destroyed the city then a moment later you pass the glass and steel giants that made Chicago famous. A walking tour is equally as cool, with the roar of the “L” above your head, you forget that the train just a few feet above you was build back in 1892 and has been speeding us along ever since. A stop in the Sears tower or John Hancock building is a thing you must do; ride the elevator to the viewing decks and gaze out on a clear day at 4 states and a stunning view of the lake. Head over to Chinatown and stop in Triple Crown for a wonderful meal,and then of course as previously stated a trip to the friendly confines aka Wrigley field is a definite must. Chicago is a truly magical place and a day or weekend or even a week does not do it justice, there are a million little hidden treasures here and each time you visit you find another one, like finding a dollar in a old forgotten book, there are surprises everywhere. And oh yea, don’t expect wind around every corner, it’s called the windy city because long ago in days when you could bump into Al Capone walking down lower Wacker, Chicagoans bragged non stop and rightfully so about a city they loved so much, and since then that nickname that other cities gave us stuck.
I miss Chicago! I have been a few times - but you know what is missing from this list? The girly meccas of “American Girl Store” and a visit to see Oprah Winfrey!
Never been but I would love to go!!! My husband wants to go to Wrigley and I wanna see Oprah.
@Kat and Kiera—I am with you, about Oprah. That would be top of my list when visiting Chicago.
@Mike-thanks for the wealth of information on Chicago—you certainly seem to know your stuff!
@ Dan–what is the TMLMTBGB
@ Tom–hmmm, a large city with friendly people? that i would like to experience!
Our niece lives right on Lake Michigan and is foreveer asking us to visit. I know now, after reading your commentary, that we will. I am anxious to try Morton’s and the Billy Goat Tavern. Walking down Michigan Avenue and riding the L–musts; and the museums-any of them—-thanks for convincing me we need to go…..
Just this one thing, bro.. This is quite a captivating chat hi guys! Heck yeah!;)