Matthew DeJong is the owner of Winding Road Productions, specializing in feature films, documentaries and video game production. Through his travel writing, he encourages young families to conquer their fears and explore the world with their children.

New York City is a perennial favourite for many northeastern families wanting to get away for a long weekend, a spring tune up, or a late summer back-to-school splurge. However, the next time you feel the urge for a few days away, try heading west to NYC’s underestimated cousin, Chicago.

Cubs celebrate winning the 2016 NL Central Division Championship at Wrigley Field (Photo by J.Geil for Chicago Cubs)

Cubs celebrate winning the 2016 NL Central Division Championship at Wrigley Field (Photo by J.Geil for Chicago Cubs)

As the third largest city in North America, Chi-town qualifies as a sprawling metropolis filled with shops, thrills, and experiences, while leaving out some of the Big Apple frustrations. For instance, those pained by bumper to bumper grinds and a sea of taxi cabs might be pleasantly surprised to find a system a lot less clogged and more accessible to desirable areas North and South of the City. As well, the sheer pressure to fulfill “have tos” in other cities fades away as Chicago offers a lot of “want tos” for those whose schedules are tight. For example, for sports lovers, possibly a tour through Wrigley Field to frisk the centre field ivy or witness one of the oldest score boards in existence might be considered sacred. But if the Cubs are out of town, a visit to the

Original Comiskey Park Home Plate (Matthew DeJong)

Original Comiskey Park Home Plate (Matthew DeJong)

White Sox’s U.S. Cellular Field (starting Nov. 1, it’ll be known as Guaranteed Rate Field) is always a safe bet for a fun night, especially if you get your picture taken at the original Comiskey home plate in the parking lot by gate 5, one which Shoeless Joe would have slid into before being suspended in 1919 along with the rest of the Black Sox. And for those wanting great sports at a slightly cheaper fair, Chicago has one of only six major league softball teams, the Bandits, located appropriately on Jenny Finch Way, where sixteen dollars a seat can get you very close to the action and possibly an autograph or two after the game.

If you are longing for big city shopping, the Magnificent Mile is what it claims to be. Boasting the third highest retail rent in the country, you’d be right to expect world famous NYC subsidiaries like Macy’s, Saks Fifth Avenue, and Nordstrom’s. But the street is also accented by such fan favourites as ­­­­Dylan’s Candy Bar, where you can have colourful parties for your little ones while sampling Jimmy Fallon’s favourite candy (Nerds, of course!) from the Famous Favourites wall.

Willis Tower's Sky Deck (Matthew DeJong)

Willis Tower’s Sky Deck (Matthew DeJong)

For those with a penchant for learning, there are riverboat tours that will guide you through some of the world’s finest architecture. As many early buildings were destroyed by the Chicago fire in the late 1800s, the skyline is known for its innovation rather than its historicity, save for the landmark Water Tower, built in 1869 and one of three buildings untouched by the blaze. Other interesting structures include the Crain Communications Building, a gleaming sail which mimics fun in the harbour, the Aqua Skyscraper, whose balconies are so innovative you might have to look twice to confirm water is not pooling down its side, and the art deco Carbide and Carbon Building — local lore suggests that its champagne bottle rendering was an intentional affront to prohibition sensibilities. If your youngsters are complaining about your desire to look at buildings from afar, surprise them by taking them to the Sky Deck. Perched on the 103rd floor of the Willis Tower, formerly the Sears Tower, once the tallest building in the world, and even rocked by Ferris Bueller during his infamous day off, the Sky Deck Ledge houses several glass boxes which extend over the city, providing an unencumbered view of the side walk — 1,353 feet below!

For learning of different kind, tours of Chicago’s gangster past are plentiful. When travelling with your brood, though, you will want to take into consideration your children’s ages and what they will be exposed to. For example, there were several tours we knew were not appropriate for our 10 year old. But, after careful research and phone calls, we found that Chicago Crime Tours did not glamorize the terrible deeds performed by the city’s most notorious villains, but showed, through Dillinger’s last breath or the St. Valentine’s Day Massacre, that the past is important to how we live in the future.

Beluga Whales (©Shedd Aquarium/Brenna Hernandez)

Beluga Whales (©Shedd Aquarium/Brenna Hernandez)

If your family needs a break in the heart of the city, Chicago is blessed with an elaborate network of beaches, whose temperatures are refreshing, and whose sand is remarkably clean. And if water fun is your thing, then you want to visit Shedd Aquarium, the second largest aquarium in the world according to Shedd, who stay clear of the controversy of other such parks by employing researchers and rescuers, and not subjecting the sea life to endless bouts of twirls and tricks.

As for food, of course deep dish is so popular that Pizzeria Uno, who created the first pizza of its kind in 1943, had to add a second restaurant, appropriately titled Pizzeria Due. But tour guides will often tell you that if you are not trying to add winter weight, then the best option is the Chicago-style hot dog. Locals will suggest there is none better than a “dragged-through-the-garden” from Downtown Dogs. They will serve your Vienna Beef wiener with mustard, white onions, relish, a dill pickle spear, tomato slices, hot peppers, celery salt on a poppy seed bun.

Chicago Shakespeare Theater at Navy Pier (Matthew DeJong)

Chicago Shakespeare Theater at Navy Pier (Matthew DeJong)

Finally, with a reputation for being a tough town, Chicago seems a lot cleaner, more accessible and friendly than it did 20 years ago. As many major urban draws have revamped their downtowns, Chicago’s is one that you can often feel comfortable visiting, even after dark. Albeit, stick to well-known spots like Navy Pier, a 100 year old indoor/outdoor playground for kids and parents alike. The Children’s Museum, Chicago Shakespeare Theatre, and Driehaus Gallery of Stained Glass are simple distractions from the myriad of boats that add life to the harbour. But for a truly northern experience far from home, day or night, visit the coolest place at the pier: Skate by the Lake. For a mere fifteen dollars, your family can rent skates in the middle of the hottest heat wave, as the outdoor ice rink at Polk Bros Park is comprised of 10,000 gallons of Lake Michigan water kept cold by a network of 288 underground pipes that maintains 4 inches of ice all year round.

As parents wanting hotels on a budget, make sure you avoid Expedia, who advertised a La Quinta, but actually booked us into the hotel next door, in rooms that were less than desirable, one almost unlockable, and a telephone call for clarity revealed a help line that was unable to help, at all. However, if you have a little more to spend, our spirits were lifted by the InterContinental, easily one of the greatest hotels we have ever stayed in, complete with a 10th floor pool that would rival a Grecian palace, and a staff punctuated by a bell-hop extraordinaire.

Once you leave Chicago after a restful few days, don’t forget to book pleasant detour before returning home. If wanting one last spontaneous chance to clothes shop for your growing family, there are many beautiful towns such as Ann Arbour, with kid-friendly hotels like the Holiday Inn and familiar restaurants to satisfy the pickiest of eaters.

When returning from Chicago, you will most likely find yourself more rested than other big city trips. And friends and family who spent their time in an overpopulated, overcrowded, and over-visited places like NYC might just notice a spring in your step and a little more “windy city” in your sails.

To keep up with Matt and his travels, you can find him on Twitter: @DeJongMatt


Fly.com Expert Tips


How To Get There: Chicago is served by two airports: O’Hare International Airport and Midway International Airport. O’Hare is about 17 miles northwest of downtown, while Midway is approximately 8 miles southwest of downtown. O’Hare is served by over 40 domestic and international airlines including American Airlines, JetBlue Airways and United Airlines. Midway is served predominantly by Southwest Airlines with Delta Air Lines and Porter Airlines offering limited service.

The cheapest way to get into the city from either airports is using Chicago’s train system known as the “L” (short for elevated), which costs $2.25 per ride. The blue line “L” from O’Hare takes about 45 minutes to get into the city, and the orange line “L” from takes about 30 minutes. A taxi ride from O’Hare will run about $40-$50 and from Midway, about $30-$40.

More information about area transportation for O’Hare is available at here, and for Midway, here.

Best Time To Visit: Unless you want to experience a real winter, the best time to visit Chicago is either spring or fall, when the weather is mild, without being too hot, as summers in Chicago can climb up into the 90s. While there are some festivals and events in spring and fall, such as St. Patrick’s Day Parade & River Dyeing and Baconfest, most of the major ones are held in summer such as Taste of Chicago and Lollapalooza.

Sample Fares: Calendars display lowest roundtrip fares over the next 90 days to Chicago from:

* All fares are roundtrip including all taxes and are accurate at time of publication. For updated pricing, conduct a new search on Fly.com.


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Chicago Skyline from Museum Campus (Matthew DeJong)

Chicago Skyline from Museum Campus (Matthew DeJong)

Featured Image: Chicago Skyline in Fall (Shutterstock.com)

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