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CityPASS Home  »  City Traveler Blog  »  A Perfect Weekend in Chicago

A Perfect Weekend in Chicago

You’re not ready for winter yet. Neither is Chicago, and autumn is the best time of the year to visit the Windy City. There are fewer crowds, there’s less humidity and the fall colors provide the perfect dressing to this majestic and fascinating town.

When I arrive to a new place for the first time, I like starting off with a get-acquainted tour with a city’s finest features. In Chicago, that means architecture, food, shopping, great museums and sports.

You can get a great overview relaxing on a Wendella Architecture River Boat Tour. Leaving from its dock at the Trump Tower, the smooth, 75-minute, stocked-bar cruiser floats by Chicago’s stunning buildings. The tour’s expert guide will point out the city’s wide range of architectural styles (Chicago School, post modern, art deco, international) designed by notable architects such as Mies van der Rohe, Bertrand Goldberg, and Skidmore, Owings and Merrill. Are you familiar with their work? Me neither, but you will be wowed by it by the end of the trip.

During the cruise, you’ll learn how the city’s skyline was rebuilt from the famous Chicago Fire of 1871. And you’ll be thrilled to learn that the Chicago River is no longer an open sewer — and hasn’t been since 1900. Before then, the river flowed east toward Lake Michigan, polluting the drinking water of people living in Chicago. Unfortunately, thousands died from water-related diseases, so they worked to reverse the flow of the river. Chicago put its broad shoulders to work, and built a 26-mile canal dug 15 feet deeper than the Chicago River. The Sanitary and Ship Canal opened on January 2, 1900, and the Chicago River began to flow backwards.

While we’re on the subject of architecture, you’ll want to use one of your Chicago CityPASS tickets after the boat ride to whoosh to the 94th floor of the John Hancock Observatory. Not only do you get front-of-the-line admission the honorable way (instead of pretending to have a handicapped, elderly relative), you can enjoy a 360-degree views of Lake Michigan, the North Shore, downtown Chicago, and south to Indiana on Chicago’s only open-air Skywalk. It’s a great place to relax with appetizers and drinks too.

Because the John Hancock Observatory is located on the famed Magnificent Mile, you can stretch your legs with a stroll along one of the world’s great boulevards toward Grant Park. You can literally consume all your time along this stretch of the city, strolling by residences, boutiques, world-class restaurants and some of the finest museums and art galleries on the planet.

It’s another reason to keep your CityPASS booklet handy. Along the Magnificent Mile, you’ll find Shedd Aquarium, the Museum of Science and Industry, and the Art Institute of Chicago, which I insist has one of the most glorious collections of art anywhere. Not only does it have the finest Impressionist collection outside Paris, you can see American Gothic in person. Check out the variety of Chicago attractions you can visit for a fraction of the original cost.

Fine dining
Chances are, you’re hungry and a little weary of walking. So it’s time for the kind of fine, serious, upscale steak sit-down dinner that Chicago is known for. The Gage, located right on Michigan Avenue is the perfect place to have a feast you’ll recall fondly for years to come. Other tasty options include Tanoshii, a popular sushi restaurant; The Publican for great meat dishes; and Owen and Engine, which has a chicken thigh sandwich with green tomatoes and bacon on it? Just phenomenal.

For nightlife, head to Wicker Park and see what’s playing at the Double Door. This iconic club is open five or six nights a week. The beer is cold, and if you don’t like the music that night, no worries, come again another night. Most shows are under $10. All I’m saying is that the Stones opened their world tour at the club once, and that’s really all I need to say.

Photo credit: localities.tv/images/activities)

Sunday Cycling
Eating out for breakfast is another Chicago treat, and just 1.5 miles from Wrigley Field is a place called Marmalade. Or, if you’re downtown, go to Eggsperience. Whichever place you dine, you’ll want to get out and enjoy the fresh air afterwards. Taking a bike ride along North Avenue Beach is a great outdoor activity. There are lots of joggers and bikers, the views of the skyline are wonderful and the water is clear, but shallow. It’s really not a swimming beach. Of course you didn’t pack your bike, so rentals are available.

For dinner, instead of a long sit-down meal, try a variety of Chicago’s delicious restaurants with a Chicago Food Planet Food Tour. Because it’s fall, the weather is mild enough for the walk, which takes visitors through the city’s different neighborhoods. It doesn’t matter what age or fitness level one is, this is a great way to explore and taste the city’s different neighborhoods. Plus, there are different tours depending on what you’re in the mood for:

The Gold Coast and Old Town tour stops in at “mom and pop” specialty food stores and unique ethnic eateries. Stops include Chicago’s first sushi and sake cafe, an authentic Polish bakery and Chicago’s top-rated, Chicago-style, deep-dish pizzeria.

The Bucktown and Wicker Park tour also goes to small, specialty restaurants, cafés and the city’s top pastry and dessert restaurant. Stops include a Chicago-style hot dog “stand” and a brewpub.

The Chinatown tour has cuisine from the Canton, Mandarin and Szechuan regions. Stops also include “Hong Kong-style Dim Sum and a Beijing Peking duck dinner.” I didn’t take this tour, but if you’re tired of Italian or steak, this might be a fun change of course.

Are you cool enough?
If a bike ride or parading around on a food tour doesn’t tickle your fancy, you can always wander around the Wicker Park Bucktown neighborhood for people watching, entertainment, coffee shops and lots of scarves. That’s because it is designated as one of the top five hipster neighborhoods in America. Forbes and Nextdoor compiled the list based on walkability scores, the number of neighborhood coffee shops per capita, the assortment of local food trucks, the number and frequency of farmers’ markets, the number of locally owned restaurants and bars, and the percentage of residents who work in artistic fields. Swing by after you visit some of Chicago's other attractions.

By just being there, you’re a lot cooler than you probably were before.

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