Weekend Getaway Ideas: Chicago, IL

The Willis Tower in The Loop. (c) 2010 C. Walton

Chicago, Illinois:  The Windy City, Chi-Town, all-American City.

Why Chicago?  Why not?  It is largest city in the Midwest.  It is the railroad gateway between the West and the East.  It sits right along Lake Michigan for the best views and has a river/canal that runs through, the only river that flows opposite the normal river flow, meaning it flows away from the lake as opposed to towards the lake.  It is home to one of the world’s busiest airports, and was the busiest at one time.  It is home to two of the nation’s largest skyscrapers, the Hancock Tower and the Willis Tower (formerly the Sears Tower).  Its “L” network is the largest of its kind in the country after New York.  90% of Chicago’s rapid transit system is on elevated tracks, even Downtown (“The Loop” as it’s called).  And you can buy some of the best franks and deep dish pizza anywhere on the planet.  Just don’t ever tell them any different.

Why is this a weekend getaway idea, even though Chicago is several hundred miles away (close to 700 miles)?  Well, because Chicago is one of those major destinations that is less than 2 hours away by plane, and many airlines offer service from JFK, LaGuardia, and Newark.  You have two options for getting there:  O’Hare Airport, one of the world’s busiest airports, and Midway Airport, one of the smallest major airports in the country, 1 square mile to be exact.  Whichever airport you choose, there is “L” service into the Loop.  O’Hare Airport has direct service to The Loop via the Blue Line and Dearborn Street subway, while Midway Airport has direct service via the Orange Line and the Loop Elevated.

Once you get there, there are numerous bus routes, “L” lines, and commuter rail lines to choose from to get where you are going.  You have rapid transit service from two areas of The Loop:  The Loop Elevated line which makes a square above Wabash Avenue in the east, Lake Street in the North, Wells Street in the west, and Van Buren in the south.  This elevated line is served by the Green, Orange, Pink, and Brown Lines, and the rush-hour-only Purple Line Express.  Then, you have the two subway lines, the Dearborn Street subway for the Blue Line, and the State Street subway for the Red Line.

The CTA at Lake and Wells. (c) 2005 C. Walton

As far as commuter rail goes, there’s enough service from the four main railway terminals that even non-commuters take the train into the city to avoid traffic on the major highways in Chicago.  The Dan Ryan, Stevenson, and Eisenhower Expressways and Lake Shore Drive are the main offenders, most especially during the rush hour periods.  So many people take the trains from Union Station, Ogilvie Transportation Center, LaSalle Street Station, and Millennium Park/Randolph Street Station to get to the numerous suburban Chicagoland counties as well as two other states.  METRA provides the majority of services from these stations, including the UP-North Line to Kenosha, WI.  Service to nearby Indiana is provided by the Northern Indiana Commuter Transit District with their South Shore line (formerly of Chicago South Shore and South Bend heritage) to Gary, Michigan City, and South Bend.  This line is unique in a number of ways:

1. It is the last of the  interurban railways in the country.  Many interurban railways were either converted to commuter rail, abandoned and completely dismantled, or abandoned and revived as another form of transportation.
2. It is one only two all-electric heavy-rail passenger operations in the country (the other is SEPTA Regional Rail)
3. South Bend is the only station on the South Shore Line that is situated in a different time zone than the rest of the network (Illinois and western Indiana are in Central Standard Time, while South Bend is in Eastern Standard Time).

Most bus service in Chicago is within the city limits of Chicago and its 77 neighborhoods or wards, which together is roughly half the size of New York City.  Most service is operated by the Chicago Transit Authority, with suburban service operated by the PACE Suburban Bus System.  Every bus route has a number and a name, mainly for the principal street of operation.  Such examples include the #20 Madison, #62 Archer, and #151 Sheridan.  During the rush hours, the CTA operates “rush shuttles” from parts of the Downtown area with high concentrations of office buildings to the METRA stations to that commuters can grab their trains and go home.  There is also limited-stop service (such as X49 Western Express), express service along Lake Shore Drive (such as #26 South Shore Express and #147 Outer Drive Express), and Bus Rapid Transit (such as #J14 Jeffrey Jump) service to get you where you need to go.

What to do, what to see, what to eat?

To-see list:

• Millennium Park and Grant Park:  Chicago’s premier park space and one of its largest parks.  Views of the Lake, miles and miles of bikeways and walking paths, and the Art Institute of Chicago.
• Willis Tower, formerly the Sears Tower:  The premier observation deck for the city, with spectacular views of the Lake and the city on all four sides.  Part of the observatory deck includes a glass cut-out that allows visitors to see the city underneath their feet.
• Union Station:  The passenger rail nexus of the country.  Amtrak service to New York, Seattle, San Francisco, Los Angeles, Washington DC, and Boston, as well as everything in between.  All located in a very grand and beautiful structure similar to the James Farley Post Office in Manhattan.
• Navy Pier: Chicago’s largest and premier outdoor recreational venue.  Located just to the north of the Loop, the Navy Pier has a ferris wheel, amusement rides, and many other venues popular to Chicagoans.

To-do list:

• Sports venues:  Wrigley Field on the CTA Red Line in the North Side, home to the Chicago Cubs; US Cellular Field on the CTA Red Line in the South Side, home to the Chicago White Sox; United Center in the West Side, by the #20 Madison and the CTA Pink Line, home of the Chicago Bulls; and Soldier Field along Lake Shore Drive accessible by the #33 Soldier Field Express, home of the Chicago Bears.
• Riding the CTA:  Most of the rapid transit system is elevated rail lines, which allow some of the best views of the city and different neighborhoods.  Many ethnic groups are within walking distance or a short bus ride from many CTA stations.
• Arts and Culture:  The Museum of Science and Industry, Adler Planetarium, McCormick Place, The Art Institute of Chicago.
• Michigan Avenue shopping and dining:  Shops along Michigan Avenue from Roosevelt Road to Ontario Street, which includes the “Magnificent Mile”

To-eat list:

• UNO Chicago Grill/Pizzeria UNO:  As cliche as it sounds, one of the best places to eat, from the place which it’s named and originated from.  Get the deep dish, a staple of Chicago cuisine.
• Ricobene’s: Another great deep-dish spot, but they have very good plain pizza for us New Yorkers that still feel that their pizza is the best.
• Culver’s:  Fast food, Wisconsin-style.  All natural ingredients, with dairy processed on Wisconsin farms.  You can take the UP North METRA line to Kenosha or find one within the Chicagoland limits.
• Connie’s:  Family-style restaurant in Berwyn Park, right along the METRA BNSF Line, with great diner food and possibly the best-tasting ribs…nearly anywhere.

Make sure you also check out the Taste of Chicago, the city’s largest street festival, which allows visitors to sample the city’s best fast food, treats, dessert, and other Chicago-style culinary venues.  Usually held in July, the event attracts roughly 1-3 million visitors.

Enjoy the Windy City!