Destination: Chicago

April 20, 2008 at 3:02 pm Leave a comment

Everyone should go to the Windy City.  It’s as though it was designed to be the perfect long weekend (or week-long) destination.  It’s home to terrific museums, comedy, music, skyscrapers, sports, and, of course, PIZZA!  It’s really cold in the winter and sometimes super hot in July and August, so I recommend visiting in the spring, early summer, or fall. 

Images from MalociteBNewingham, and Wiki.

Getting There & Getting Around
Fly in to O’Hare (ORD), one of the busiest airports in the country, or Midway (MDW).  ORD is 17 miles northwest of downtown, huge, and notorious for delays and cancellations.  A taxi into the Loop will be $40 or more.  The easier method is to take the CTA Blue Line (48 minutes).  Midway is 10 miles southwest of downtown, smaller, less crowded, and often cheaper to fly into.  From Midway, a taxi will be $30 or more, or you can take the CTA Orange Line train in (25 minutes).

Other options for getting there: Bus – Greyhound, Megabus; train – Amtrak; or car.  If you decide to drive in and aren’t used to the Chicagoans’ driving style, be warned – they drive fast.

Once your in the Loop, everything’s very easy.  The streets are mainly a grid and everything is consistently numbered.  The Chicago Transit Authority (CTA) runs buses and trains within the city and out to some of the suburbs.  Locals refer to the train system as the L, and tourists are a big fan of the trains – they’re super easy to navigate.

What to Do/See
Museums: Chicago has some of the best.  The Art Institute of Chicago is amazing – it’s like walking thru an art history book.  It’s a very tight collection – some of the most important and famous works of arts are housed here.  The Adler Planetarium is home to the famous Christmas show, Star of Wonder.  The Field Museum has a huge t-rex skeleton and lots of Egyptian artifacts.  The Shedd Aquarium is terrific – from fish and sharks to dolphins and whales.  The Museum of Science and Industry is beloved by those who are curious about science.  The Lincoln Park Zoo (free!) is really good for a free zoo.  Be prepared for the disturbing pacing polar bear though.  He’s supposed to be a lot better, but skip seeing him if you think you’ll find the behavior upsetting.

Shopping: The Magnificent Mile is your best bet.  This is the place to find many designer boutiques and multiple multi-story malls with large department stores.  You also might want to check out Lincoln Square, Bucktown, Wicker Park, Southport in Lakeview and Armitage in Lincoln Park.  For art or designer home goods, check out River North.

Sports: If you like sports, Chicago is definitely a good bet for you.  For football, get tickets to the Chicago Bears.  Basketball fans can catch the Chicago Bulls, and hockey fans can see the Chicago Blackhawks.  Baseball fans will be thrilled with two options – the Chicago Cubs at historic Wrigley Field and the White Sox at U.S. Cellular Field.  Be warned – don’t support the visiting team unless you’re prepared to have food/trash chucked at you.

Theater: Improv comedy is big in Chicago; check out Comedy Sportz, the Annoyance, I.O., and the Playground.  The Broadway in Chicago outlets are a good bet for musical lovers.  Currently showing or coming soon: Wicked, Jersey Boys, Sweeny Todd, SHOUT!, Avenue Q, Dirty Dancing, and Mary Poppins.  I managed to snag a lottery ticket for Wicked last time I visited (go to the Borders next to the theatre about 2.5 hrs before show time, drop your name in a box, and pay $25 ea for front row center seats – awesome).  It was really great – not original cast great, but still really really good.  The Blue Man Group is another great choice (be sure to talk through the tubes while you’re waiting for the show to start).

Fans of skyscrapers have two really good options – the Sears Tower Skydeck ($12.95-25) and the John Hancock Observatory.  I prefer to just visit the Signature Lounge at the top of the John Hancock Center – it’s free to get there.  Then you can use the money you would’ve paid for an elevator ride to buy a drink to enjoy while you check out the view.

An architectural boat tour (CAF, Chicago Tours, Chicago Line, etc.) is a must in my opinion.  You’ll learn some of the history of the city and see some amazing sites, including a view of the skyline from Lake Michigan.

Outdoors: If you enjoy the outdoors and the weather is good, visit one or more of Chicago’s parks (Lincoln Park, Lakeview, Rogers Park, Grant Park, Millennium Park, Jackson Park) – or the beaches of Lake Michigan.  According to Wiki Travel,

Oak Street Beach and North Avenue Beach (in the Near North and Lincoln Park) are the fashionable places to sun-tan and be seen, but Rogers Park has mile after mile of less pretentious sand and surf. Rainbow Beach in the Far Southeast Side is actually one of the city’s nicest, although it is rarely visited by sun lovers from outside the neighborhood.

Extras: During the summer on Wednesdays and Saturdays, check out the fireworks at 9:30pm from the Navy Pier (you can see them without going all the way to the Pier though).  At New Year’s, head for the Navy Pier for the best fireworks show I’ve seen outside of Disney World.  Also, check out whether there are any festivals on when you’re visiting – there are tons, so it’s probably harder to find a time when there isn’t at least one festival going on.

Where to Eat & Stay
Eating in Chicago is SUPER important.  First up – pizza.  If you have only one meal, I say make it pizza.  Heck, if I’m only there for a weekend, I’ll eat pizza more than once.  Be prepared for it to take a while; those pizzas are so deep that they take some time to cook.  My first love (for Chicago deep dish pizza) was Gino’s East.  That egg-y crust and huge amount of cheese is to die for.  More recently, a friend of mine told me about Lou Malnati’s.  Holy cats – that stuff is even better than Gino’s.  But don’t tell Gino’s I said that.  I still adore Gino’s.  You can go to the birthplace of Chicago-style pizza, Uno, but that’s a chain and…. well, Lou’s and Gino’s are better.  And don’t be fooled by Due’s – it’s just Uno under another name.

There are tons of other great and/or famous restaurant options in Chicago for every meal – Harry Caray’s (Italian steakhouse), McCormick & Schmick’s (seafood), Morton’s (steakhouse), Smith & Wollensky (steakhouse), Bongo Room (brunch), Ed Debevic’s (diner)…  Gosh, the list could go on forever.  Check out Citysearch for the type of food you’re looking for or get recs from the Chowhound gang.

Again, I’m spoiled when it comes to where to stay in Chicago – I just stay with my bff Elizabeth!  If I just had to stay somewhere, I’d check out the Sofitel Chicago Water Tower, the Trump International Hotel & Tower, Four Seasons, or the Peninsula Chicago.  Then I’d get realistic and book somewhere fabulous but more affordable like the Swissotel, the Palmer House Hilton, or the Fairmont.


Entry filed under: Destinations, TheStates.

An – a restaurant in Cary Extra charges for seats in COACH?!

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )


Connecting to %s

Trackback this post  |  Subscribe to the comments via RSS Feed


April 2008
« Mar   May »

Most Recent Posts

%d bloggers like this: