Chicago, Illinois is known as the “City of Big Shoulders”.  While it is in the middle of the introverted American midwest – it thinks big and carries itself as a hardworking blue-collar city.  Little cultural pretense, yet world class sights and amenities.

We’ve been to Chicago many times but hadn’t been there on a family vacation for almost a decade before we went for a long weekend this past July.  It’s not a location that likely gets a lot of visibility as a vacation destination outside of the midwest, but it is a terrific place to visit.  If you’ve seen New York and Los Angeles – it is worth a visit to Chicago to see another side of the United States.

Here are some of our favorite spots:

1. Michigan Avenue Skyscrapers

Chicago is home to the skyscraper.  Leveled after the Great Chicago Fire of 1871 when more than 2,000 acres were burned to the ground.  Chicago was rebuilt behind the architectural visions of Daniel Burnham, Louis Sullivan, and Frank Lloyd Wright.  Michigan Avenue is Chicago’s main thoroughfare and it is an impressive collection of skyscrapers in the city that invented them.  Walking Michigan Avenue is a pleasure from the Chicago River up to the limestone Water Tower & Pump House – the only significant structures said to survive the fire.

2. The Second City

Chicago has long played cultural second-banana to New York.  While Chicago has Michigan Avenue, New York has Fifth Avenue.  Where Chicago has the Sears Tower, New York has the Empire State Building.  Where Chicago has Lincoln Park, New York has Central Park.  You might be tempted to say the same about comedy, but Chicago’s Second City is the progenitor of New York’s Saturday Night Live – and many would argue is still better.  In Chicago’s Old Town area, Second City was the home of a Who’s Who of comedy: Alda, Ackroyd, Arkin, Belushi(s), Candy, Carrell, Colbert, Farley, Fey, Long, Murray, Myers, Pohler, Ramis, Rivers, and Willard.  Second City performs 2-3 shows a day (book in advance) and there are great restaurants (like Woodie’s Flat) just down the street.

3. Chicago Institute Of Arts

Chicago is definitely first in comedy, and many also think they are first in art museums.  The Chicago Institute of Art – anchoring Chicago’s Millennium Park – was voted the Top Art Museum in the World by TripAdvisor.com.  That’s no small feat considering competition from NYC’s Met, MOMA, Paris’ Louvre & d’Orsay, London’s National Gallery, and St. Petersburg’s Hermitage.  We’ve visited all of those museums on different vacations and I would say it is definitely in that group.

4. Chicago Museum Campus

Not far from the heart of Chicago’s Loop is the lakeshore Museum Campus which features the Field Museum, Shedd Aquarium, and Adler Planetarium.  The three facilities are magnificently sited and are each world-class in their respective disciplines.  The Chicago CityPass (about $90) gives you admission to all three of these, the Art Institute, Willis Tower, and Museum of Science & Industry.  All are terrific stops.

5. Marshall Field’s State Street Store 

If you are fan of the grand old big city department stores of the Twentieth Century, you won’t be disappointed by the massive Marshall Field’s store on State Street.   Now operated by Macy’s, the building is the third largest retail store in the world and was highly influential in developing the department store concept internationally.  It features multiple grand atriums, an enormous Louis Comfort Tiffany mosaic, iconic street corner clocks, the Frango candy kitchens, and elegant Walnut Room (“for ladies who like to lunch”).  Store founder Marshall Field was famous for his slogan “Give the lady what she wants.” His store pioneered revolving credit, Christmas window displays, and personal shoppers.  Harry Selfridge (of London’s Selfridge’s) worked at Marshall Fields as an executive for many years, taking Field’s ideas to Europe.

6.  Chicago Ball Parks

Chicago sports two baseball teams: the much-loved, north-side Cubs and the blue-collar, south-side White Sox.   The Cubs are the reigning World Champions and the White Sox won in 2005.  The wins broke a combined 100+ years of fruitless baseball for the two teams.   The Cubs’ Wrigley Field is a historical treasure, while the Sox’ New Comiskey / US Cellular / Guaranteed Rate Field also has its charms.  While the experience in each park is unique, they are both worth a visit.

We stayed in Chicago for a long weekend – four days, three nights.  That was the perfect amount of time to get in & around most of these sights.  You could stretch a visit to a week and include some other activities and areas.  On my honorable mention list would be the Museum of Science & Industry, the Frank Lloyd Wright tours in Oak Park, the Brookfield Zoo, and a night out on Rush Street or at Navy Pier.

Image Credit: MrFireStation.com; Wikipedia (Ballparks)