People having fun ice skating at ice rink in downtown Chicago. Beautiful snowstorm night and South Michigan Avenue lights.

From perusing holiday windows to embarking on a "Polar Express"-themed train ride, there's plenty to pique your interest in Chi-Town this winter. (Getty Images)

With the Chicago Cubs' historic World Series win sending Chicagoans and visitors into a festive frenzy, the holidays in the Windy City will certainly be filled with throngs of tourists with vibrant celebrations in full force. Whether you want to shop, ice skate or admire bright light displays, here are five reasons to celebrate the season in Chi-Town this winter.

[See: 10 Underrated Places With Fantastic Holiday Celebrations.]

You Can Enjoy Ice Skating and Other Wintry Pastimes

There are a variety of places to lace up your skates in Chicago, including next to the Bean at the McCormick Tribune Ice Rink in Millennium Park and at nearby Maggie Daly Park, which offers a skating "ribbon" that winds through the park. Other options include the indoor rink at Navy Pier, which is decked out for the holidays, and the square rink at the Lincoln Park Zoo, where you can also stroll past their holiday light display. If you're on a tight budget, the Go Chicago Card offers discounts on admission and rides at Navy Pier, Lincoln Park Zoo and 24 additional area attractions, and lets you bypass waiting in long lines.

You can even ice skate above the city at The Peninsula Chicago's Sky Rink surrounded by pine trees, twinkling lights and the city's famous skyscrapers. Located four stories above street level, The Peninsula's ice skating rink boasts dramatic city views of the world-renowned John Hancock building and Michigan Avenue. What's more, you do need to be a hotel, restaurant or spa guest to skate at the rink; there is a suggested donation of $10 to $15, all of which supports local charities.

You Can Shop Along the Magnificent Mile and Browse the Shops at the Loop

Chicago offers several iconic shopping districts that are perfect for getting into the holiday spirit with windows displaying elaborate displays and lights galore. The Magnificent Mile Lights Festival brightens Michigan Avenue with a million lights topping 200 trees all along the main thoroughfare. And if you're traveling with youngsters, don't skip checking out American Girl Place or the Lego store.

The Loop, which sits south of the Chicago River, is the dream spot for department store shopping. Macy's store windows are a sight to see all on their own; the building itself is a National Historic Landmark and features a 45-foot tall Christmas tree inside. Plus, the Christkindl Market in the Loop district makes a wonderful spot to find unique German gifts like hand-blown glass ornaments, nutcrackers, cuckoo clocks and traditional German cuisine.

You Can Get Your Cubs Fix

Whether you're a bonafide baseball fan or visiting the city for the first time, you can't visit Chicago without paying tribute to the Cubs. This beloved team made history after a 108-year World Series drought and there are many iconic sites to enjoy a little of the Cubs' magic. Hop on the L train to Wrigleyville for a stop at the famed Wrigley Field to get a snapshot of the marquee, which now reads "World Series Champions."

It's also worth a visit to one of the area's popular bars, such as Murphy's Bleachers or the Cubby Bear, where you can raise a toast to Harry Caray. Stop for dinner at Harry Caray's Italian Steakhouse in the River North district, which is filled with Cubs memorabilia and a statue of a cow wearing Harry Caray glasses. The historic building is the former home of Chicago gangster Frank Nitti and even has an underground tunnel where he could slip out without being seen. Choose from one of their top-quality steaks and don't skip sampling the Four Cheese Mac 'N Cheese. Restaurant owner Grant DePorter correctly predicted 2016 as the magic year for the Cubs' World Series win, noting numerous stats and key figures that tied to the number 108.

[Read: 8 Great American Winter Road Trips.]

You Can Indulge in an Iconic Deep Dish Pie

What's a trip to Chicago without a slice of their famous deep dish pizza? Be prepared for long wait times at favorite pie joints, such as Gino's East, Lou Malnati's and Giordano's Pizzeria. Though the wait can take longer than an hour, your taste buds will thank you.

You Can Embark on a Holiday-Themed Train Ride

As a fun annual tradition, the Chicago Transit Authority decorates one of its trains in bright lights and sends Santa and his elves along for the ride, passing out candy canes to riders. The CTA holiday train runs from the Friday after Thanksgiving through Christmas on select lines. Visit the CTA website for specific lines and times. You can also take a ride on The Polar Express, leaving on Amtrak from Chicago's Union Station. Riders are encouraged to wear their pajamas as they step onto the train and listen to the legendary story of a little boy who has lost his belief in Christmas in "The Polar Express," a children's tale written by Chris Van Allsburg. An added bonus of The Polar Express train ride: Everyone gets a souvenir sleigh bell and hot chocolate tumbler.

Where to Stay

Chicago hotels shine at this time of year with stunning holiday decor and massive Christmas trees. Some great options include the Kimpton Hotel Monaco Chicago, located along the Chicago River between River North and the Loop and close to Michigan Avenue, the ACME Hotel Company, Conrad Chicago and the Hilton Chicago. The Kimpton Monaco Chicago offers scenic window seats in each room with striking city views. Plus, their Urban Holiday package throws in a holiday blanket, hot chocolate, cookies and books for snuggling up in the window seat and enjoying the city lights at Christmastime. Meanwhile, the ACME Hotel Company offers a fun respite in the River North district and features innovative perks such as Google Glass for guests, apple watches on loan, and hot spots on the go.

[See: 10 Bucket List Winter Family Vacation Experiences.]

Conrad Chicago, which recently debuted in November, is another ideal choice thanks to its convenient location along the Magnificent Mile. To mark its grand opening, the hotel is offering guests the chance to book two nights and receive a $100 food and drink credit. And the Hilton Chicago, located across from Grant Park, especially appeals to kids eager to spread holiday cheer with an iconic 24-foot Christmas tree in the lobby along with a 6-foot-tall gingerbread hotel.

Tags: travel, Chicago, vacations, holidays


Lyn Mettler is the hotels contributor to U.S. News and also writes about destinations, adventure travel and flying free using miles and points. She is the author of “The Step-by-Step Guide to Flying Free on Southwest” and blogs on the topic at GotoTravelGal.com. She is a longtime travel public relations professional and writer based in Indianapolis, whose articles have appeared in Executive Traveler, Private Air, Legion magazine, the National Catholic Register, MSN and other outlets. She and her family enjoy exploring the U.S. on active trips and her favorite destinations include the Rocky Mountains, Chicago, Orlando and California. Follow her on Twitter, Pinterest and Instagram at @GotoTravelGal.

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