The Cozy (albeit windy) City


Musicals, museums and the Magnificent Mile are Chicago highlights

By Natalie Hollingshead


In the heart of downtown Chicago, a cobblestone bridge passes over the Chicago River. Stately buildings, such as Trump Tower, rise overhead. Lake Michigan looms in the distance, its waters reflecting the pulse of city life all around.

Although we’re in a hurry — the curtain call for an off-Broadway showing of “Wicked” is in 20 minutes — my husband and I pause on the bridge. Our stomachs are full from feasting on deep-dish pizza at the famous Pizzeria Uno, and in that bliss, we can’t help but notice how peaceful, welcoming and even cozy the densely populated city feels.

Despite its big city industries, inventions and infamies (think of the movie “Chicago”), the metropolis is surprisingly friendly and decidedly fascinating. Yes, the Windy City took our breath away — and it wasn’t because of that legendary breeze.

Home to one of the world’s tallest skyscrapers, the world’s busiest airport and perhaps the planet’s most well-known woman — Oprah Winfrey — Chicago could be intimidating. But if you’re planning a trip to the city, plan to be pleasantly surprised. Chicago is bursting with beautiful sights, forthcoming people and family-friendly activities. Not quite what we expected from a city some 2.8 million people call home.


The Oprah and More

Speaking of Oprah, if you’re planning your sojourn to Chicago with the sole hope of attending The Oprah Winfrey Show, make sure you secure tickets ahead of time. Tickets aren’t released at the door or sold to the highest bidder. The only way to get tickets is by calling the reservation phone line, which, unfortunately, is only open for a few hours each month. So you’d better be dialed into redial if you’d like to attend.

If you don’t land tickets, don’t fret. There is plenty to do outside Harpo Studios. In fact, the Windy City has so many amusements you won’t be able to take it all in on one trip. Like us, you may need to draw straws to choose between off-Broadway shows, professional sporting events and first-class museums.

For example, downtown Chicago’s 57-acre Museum Campus is home to the Field Museum, Adler Planetarium & Astronomy Museum, Shedd Aquarium and Soldier Field (home to the NFL’s Chicago Bears). We spent most of one day at the Field Museum, home of Sue, the world’s most complete Tyrannosaurus Rex skeleton. There, we stood “toe-to-paw” with the mounted man-eating Lions of Tsavo and walked through the real tomb of Unis-ankh, a pharaoh’s son, whose mummy lay in the burial chamber under our feet.

Another afternoon was spent at the sprawling Shedd Aquarium, built just east of the Field Museum. We splurged on the Premium Day Pass, which at $27.50 included access to all seven exhibits and a seat at the 4-D presentation “Planet Earth: Shallow Seas,” taken from the acclaimed BBC series of the same name. The 4-D features included squirting water, moving seats and blowing air. Make sure you buy a pass that includes the daily dolphin shows, too.

It will take at least two days to take in all of the exhibits at The Museum Campus, and even then, you may just be skimming the surface. Research each museum’s special event days before you go — with a little planning, you may be able to take in one or two exhibits for free (see sidebar).

If you visit Chicago in the summer, a detour to the Navy Pier may be in order. Adjacent to Lake Michigan, Navy Pier is filled with 50 acres of shops, restaurants, gardens and entertainment. We weren’t blown away with the shops — filled mostly with tchotchkes and trinkets — and recommend you save your green for the Magnificent Mile. However, a ride on the 150-foot Ferris Wheel made our detour worthwhile.

Known to shoppers as the Magnificent Mile, the Michigan Avenue thoroughfare is home to some of the city’s ritziest hotels, stores, galleries and eateries. Plan on spending a lot of time — if not money — checking out the eye candy.

Chicago has a thriving nightlife scene and an active theatre district. With limited-engagement and touring shows, it’s likely you can find an off-Broadway musical or comedy that will fit the playbill. We attended the hit musical “Wicked” at the glamorous, gold-gilded Oriental Theater. The untold story of the witches of Oz, “Wicked” is currently Chicago’s longest-running musical.

When night falls, Chicago shines. You can take in panoramic views of the city from the Sears Tower or the John Hancock Observatory. A kind Chicagoan turned us onto The Signature Room restaurant on the 95th floor of the Hancock Observatory, where the view is as majestic as the observatory floor, less the $12 per person charge.

Or, there’s always the bridge.


If it’s free, it’s for me

With so many attractions to visit in Chicago, the tab can quickly add up. Save money by planning your trip on the dates when local museums and sights offer free admission.


Adler Planetarium — Charter One Foundation sponsors free admission at the planetarium. Visit


Chicago Children’s Museum — Target Free First Mondays waive the admission fee for visitors ages 15 and under. Kraft Free Family Night gives free general admission for all visitors on Thursday nights from 5-8 p.m. See for details.


Field Museum —Target Second Mondays grant free general admission and free admission to specially ticketed exhibits the second Monday of each month. In addition, general admission is free the weeks of Sept. 21-16 and Oct. 26-31. Visit




Natalie Hollingshead is a former magazine editor turned freelance writer and editor. She writes regularly about home, family, food and travel for a handful of publications, and is co-author of the book "Happy Homemaking” (Cedar Fort, 2012) with Elyssa Andrus. A native of Alberta, Canada, Natalie lives in Orem with her husband and their three children.

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