Domestic Food & Wine Local Destinations Travel & Hotels



Chicago is such a great city.” I can’t tell you how many times I heard this and thought, “Wow, clearly you don’t get out much.” Why would I take a trip to the “Windy City” when I could go to the land of s unshine and ocean views, like Hawaii, Miami, and Los Angeles?

I knew very little about Chicago. I had a few layovers in the airport. I often heard people saying “I have to go to Chicago for work”. Yes, airports and work. That didn’t sound very fun to me. After all, I lived i n San Diego. Why would I go to Chicago?

Along the way, I made several good friends from Illinois and not once would they boast about their hometown city. I just assumed it was because there was nothing to say about it. Chicago just never f ound its way onto my radar.

And then randomly, I was Chicago bound. Like any good traveler, I began asking around for places to s ee and things to do.

Eyes lit up. Stories were told.

I was bombarded with recommendations on where to go: the Russian District for posh clubs and dining, Wrigleyville for pubs, the Magnificent Mile for shopping, the Navy Pier along Lake Michigan, and countless rooftop clubs. The recommendations were endless and I actually started to get excited. I felt like the world was keeping a secret from me. Why in the world does everyone love Chicago, but never talk about it or recommend it for a vacation?

I was curious.

I landed in O’Hara airport and met up with an old traveling buddy, Mary Anne. I flew in from San Diego and she was from Seattle and neither one of us had ever been to Chicago for more than a day. We discussed transportation options with some locals at the baggage claim. Train, shuttle, cab? Since we didn’t know the city at all, it was recommended we take a cab thirty miles into downtown. However my girlfriend was insistent we take the train (something about “going g reen” and being part of the solution, not the problem).

I reluctantly hoofed it off to the train station grumbling and switching from my pretty corked wedges into flip-flops for the hike ahead. A journey it was, although you couldn’t beat the price: $2.20 one-way to downtown. Too bad it ended up taking close to 2 hours to get to our hotel due to a train malfunction. Two train transfers, a bus, and a cab later, we arrived at our hotel. Take the cab; trust me it’s worth the $50.

We arrived at the Hyatt downtown and ended up in a corner suite overlooking Lake Michigan and downtown. I was instantly in love with Chicago. Late for our dinner reservations, but starving after 7 hours of traveling and that torturous train ordeal, we ordered some wine and cheese and pushed back the reservation to take in the colors of the sun setting beyond downtown and watched the city l ight up.

David Burke’s steakhouse was our first stop and it was absolutely magnificent. The wait staff was ridiculously friendly and we followed the lead from our server on wine pairing, and food recommendations.

The steaks, appetizers and dessert were just amazing. The owner, David Burke and Executive Chef Rick Gresh, came out to share a glass of wine and liven up our night. Being from Philadelphia originally, I just loved David Burke’s authentic Jersey boy ways and accent (picture a better looking version of Tony Soprano). I was fully impressed to learn that he began as a chef and now owns and operates six David Burke’s Steakhouses across the county. All of their beef comes from Creekstone Farms in Kentucky and they have an in-house dry-aging room, which we toured and got a very interesting l esson in aging beef. The food, wine and service were just fabulous.

Next we were off to the clubs. We started at Manor, which was very upscale but completely packed. It was the hot scene in town, but this is the type of place you plan ahead and get a table and bottle service, otherwise you get lost in the crowd. We didn’t last too long there before we ventured down the street to Angels & Kings, a much smaller venue with a great DJ spinning and very eclectic crowd. We danced into the night. Chicago’s nightlife is much like New York, in that you can party through all night long into the AM (if you pace y ourself, that is).

The next morning it was time for our biking tour of Lake Michigan. We arranged to rent bikes from the James Hotel which seemed like a great way to take in the city. I stepped into a beautiful 75 degree day with not a cloud in the sky and a cool lake breeze. It was recommended that we wear a helmet, but I was a little too cool for that. Mary Anne was into “safety first”, but this is coming from a girl who loves and supports public transportation. As I weaved through the traffic, I actually thought twice about whether I should have opted for the helmet, but once we made it the biking path along the l ake, I was fine.

Lake Michigan is absolutely beautiful. Just as stunning as any ocean I have ever overlooked (in the U.S. anyway). We biked down by the pier and were impressed with the scene of local Chicagoans enjoying the stunning weather and view. We cruised along the lake a mile or so and found a cute beach front café called Oak Street Beachstro with a large outdoor patio with beach chairs galore, ocean view (ok, lake, but who’s keeping track) and delicious Sangria. Again, friendly wait staff greeted us and it was at that moment I realized we had not encountered one rude person since we had arrived. As I began commenting on this to our waitress, she went on to explain that it’s how people are in the Midwest and it extends through to the city.

Hmm, a friendly city? Who knew?

So sad to leave the next morning, but much wiser, we hopped into a cab (not the train and after much debate with Mary Anne, I got my way this time). I’ll always smile when I think of Chicago and vow n ever to keep it such a secret.

Do yourself a favor and give yourself more time than just a weekend. I’m sure the possibilities are endless. So look out Los Angeles and New York, Chicago has everything you desire in a vacation, without the attitude.

CHICAGO CHEAT SHEET Sightseeing The Art Institute of Chicago Considered one of the best museums in the country. Recently opened its Modern Wing, designed by Renzo Piano, which makes it the second largest museum in the country. The place to lunch is the Terzo Piano.

Millennium Park “The Bean” by Anish Kapoor, a great curved metal statue that is quite impressive. Use an evening or weekend to see a show at the Pritzker Pavilion. Lounge outside and picnic before you listen to some of the best outdoor acoustics in the nation. The Pritzkers are famous in town as they are the family that owns the Hyatt Hotel group.

Buckingham Fountain An immense fountain that is beautiful at night. It is romantic and majestic.

Boat Tour of Architecture The Chicago Architecture Foundation hosts a boat tour of the top architecture sights in the city, we highly recommend this. Sights: Marina City, Wrigley Building, Merchandise Mart, and others.

Sears Tower Observation Deck One of the highest buildings in the world. If it is a clear day you can see across the lake to Michigan, which is quite far.

Wrigley Field Considered the granpappy of all baseball stadiums, every seat in the stadium is great because it only seats 41,000. Grab a dog, wear a cubs hat, and sing take me out to the ball game a tradition that is due in part to Harry Caray, Chicago’s beloved TV and radio announcer for the Cubs.

Casual Food Deep Dish pizza is famous in Chicago; our favorites are Pizzeria Uno or Due on 29 East Ohio Street. They have an amazing butter crust.

Try the cheese and sausage. Note that it takes about 45 minutes to make the pizza so call ahead before you get to the restaurant.

Stuffed pizza should not to be confused with deep dish. Pizza “toppings” are placed on the bottom crust of the pizza and topped with another layer of dough; sauce is then placed on top of this sheet of dough to create stuffed pizza. Giordano’s is the only place to eat this genre of pizza. Spinach and cheese is our favorite.

Portillo’s serves a solid Italian beef sandwich indigenous to Chicago, served on a soft Italian roll with beef, “giardiniera” (hot peppers),

Leave a Reply

Your email address will not be published. Required fields are marked *