They call it the windy city, but there is some dispute about what the term actually refers to. Three favorites are; the long winded speeches of local politicians; the wind that whips up off the Great Lake; or the never ending praise Chicagoans like to bestow upon their fair city. Whatever the reason, let the wind carry you to Chicago and prepare to be completely charmed.
You have two choices of airports, O’Hare International and Midway International. I don’t know how you like to travel, but give my husband and I ease over hardship anytime, so by all means use Midway. An eyesore a decade ago, Midway has since become such an effortlessness airport that it makes O’Hare feel like it’s in another country. O’Hare is the second busiest airport in the nation, and comes with all of the headaches and delays that distinction carries. Add the fact that it is a slow 45 minute drive (on a good day) from downtown while Midway is more like 20 minutes and you get the point. Southwest and a few other carriers have direct flights and really great airfares right into Midway.
We all know that the winters are a little harsh in Chicago, so best not to plan your jaunt during those months. Our favorite times of the year are late spring or early fall. Not only because the weather is usually sunny and crisp but ohh those beautiful tulips are in full, awe inspiring bloom in spring, and all the leaves are changing in the fall. Either way Chicago is an explosion of gorgeous natural colors both times of year. It makes for quite a site to be surrounded by buildings that are bold, tall, constructed of hard steel or brick while at ground level you are walking amongst a rainbow of tulips, or a crimson and golden canopy of nature. It is just breathtaking.
What Do You Mean We Can Only Pick Three
Chicago is a phenomenon when it comes to the restaurant scene and believe us they live up to the praise. There are so many ridiculously good places to dine that we feel almost guilty just naming a few. With much humility we suggest a sampling of three venues, from highbrow to trendy and some good ol’ local fare. Want something tasteful; try one of our faves and also a Chicago mainstay - that’s 312 Chicago on N. La Salle Street. Catering to shoppers, theatre goers, politicians and local businesses, 312 is centrally located and is a wonderful way to appreciate the gestalt of Chicago. Serving classic Italian fare with creative twists on pasta, steak, and seafood dishes 312 is sure to please.
Looking for an easy place to gather with friends? Then try Tavern On Rush, (yeah, it’s on Rush Street, not that we are implying anything….) which features a large, sprawling bar, multi-level seating, open kitchen and shuttered windows to view the street below and around you. There is always a party going on with lots of embibing, socializing and great eats to be had. It’s also a pretty hysterical display of local Cougars on the prowl. Hold on to your boyfriend and watch the action unfold as the Martinis get knocked back. Grrrr.
Need a little comfort food? Head over to The Central on Clark Street, near Wrigley Field. Whether you are going to a Cubs game or you just want to soak in some local color, The Central is the place to be. This is basic fare like nachos, Burgers, Paninis, Buffalo Strips, Pizzas and with a fun selection of Martinis and, of course, lots of beer on tap. Grab a stool and enjoy the festivities with the locals.
We Have to Mention Wrigley Field
Speaking of Wrigley Field, whether you’re a baseball fan or not, try to take in a game. You can even legally buy scalped tickets outside its gates. Let the point be made, we love our Padres and Petco Park but when you step into Wrigley Field stadium, you have stepped into history. Not quite the “if you build it they will come” but pretty darn close. The energy of the crowd is intoxicating. Fans young and old still scribble their game stats. Everyone (and I mean EVERYONE) stands up for the last inning, whether it’s the top of the ninth (because the Cubs are in the lead) or the bottom (here the Cubs need to catch up); you are part of something bigger than just a ballgame. And you must try a Brat!
Don’t Miss
In a rush? Here are a couple of suggestions for things to check out during a quick visit. First up, grab an elevator and take the ride up the John Hancock Building to the Signature Room. This engineering marvel stands over 1000 feet up, and the Signature Room is on 95th floor (don’t look down unless you can handle it). If you want to see the city at ground level, take an architectural tour on the Chicago River, which is dyed green for St. Patrick’s Day. You will stop at some of the more famous museums, check out architectural masterpieces, and generally experience everything that makes Chicago a beauty to behold. Last, but not least make sure you stop by the Tribune Tower, which has pieces of the Sphinx, the Alamo, and the Parthenon cemented into the façade.
LGBT Special
As a city, Chicago couldn’t be gayer. Besides the shopping on Michigan Avenue and the Broadway caliber theatre productions Chicago is home to the famed Boystown (located in East Lakeview area, especially Haltsed Street). A must stop is the legendary Sidetrack bar (3349 N. Halsted). A staple in Boystown for over 30 years, Sidetrack is Chicago’s premier video bar. Sporting seven rooms and a cool rooftop beer garden, Sidetrack will satiate whatever itch you may have.
We all know after a few drinks food is a necessity. Thank goodness Las Mananitas (3523 N. Halsted) is just a stumble away. It’s has the usual Mexican food assortment to fill the tummy for round two at the bars. They also have killer margaritas (wait, I thought we were here for the food?).
Need a gay-friendly place to stay? Chicago holds many a venue to accommodate, but our shout out goes to the Kimpton Hotel group. Not only are they gay friendly but also pet friendly (you know how we are) and all offer a free wine happy hour to start the night off. The beds are like clouds and the pillows are like rainbows (no pun intended). Plus the staff and service are always spot on. All locations also feature great in house restaurants in case you need to just stay at “home” for the night. You’re going to need it in this town. Plan on sleeping on the plane so you won’t miss a thing on the ground.
My kind of town, Chicago.
