STAY: Book your stay at the Langham, Chicago, for an exceptional experience and the best access to shopping and activities. The iconic hotel is the epitome of comfort with timeless English style, first-class amenities and floor-to-ceiling windows for a breathtaking view of the city. I like to head out early for a run along the river and make it back in time for the hotel’s complimentary breakfast. As the city wakes up, horse-drawn carriages make their appearance. Holiday spirit is almost palpable on the Magnificent Mile, where great shopping meets festive decor. Check off your Christmas card family photo on State Street in front of the intricately decorated, giant Christmas tree in the Macy’s Walnut room. Then head over to Crate & Barrel for modern, trendy holiday window displays. Finally, grab tea in the legendary Drake Hotel, where they spare no expense decorating for the season.  

WALK: The key to Chicago is to walk it. After the Great Chicago Fire of 1871, the city became a hotbed for innovative architecture and beautiful design. The people are friendly, the streets are clean and the city’s grid layout makes for easy navigating. Among my favorite buildings are the Holy Name Cathedral and the neo-Gothic Tribune Tower. Catch some guided sight-seeing on an architectural boat tour on the Chicago River. Afterwards, make time to visit the Chicago Temple Building, home of the oldest church in the city, the First United Methodist Church. Or if you are anywhere near Oak Park, swing by the Frank Lloyd Wright Home and Studio. If you aren’t crazy about spending the day outdoors, take the family to Navy Pier for Winter WonderFest—170,000 square feet of indoor entertainment with rides, attractions and an enormous ice skating rink. Don’t miss Garrett Popcorn Shop. The classic Chicago Mix blends caramel and cheese for a flavor experience that puts movie theater popcorn to shame. 

PHOTOGRAPH: At the heart of downtown is Millennium Park, the backdrop to hundreds of Chicago events and concerts. Snap a photo in front the famous Cloud Gate sculpture (more commonly known as The Bean). I like to shoot photos with my back to the city so the skyline ends up in my shot.

Chicago has 26 miles of waterfront and is home to 552 parks.

VISIT: The Art Institute of Chicago (AIC) houses one of the country’s finest collections. Among the must-see pieces are “American Gothic” by Grant Wood, “A Sunday Afternoon on the Island of La Grande Jatte” by Georges Seurat and Monet’s “Haystacks.” But don’t just settle for the greatest hits. A number of additions left the museum with a somewhat haphazard layout. Let yourself wander and see what catches your eye. Francisco de Zurbarán’s “The Crucifixion” is a powerful image you can see in the institute’s European Painting and Sculpture wing. Saturdays are the busiest day at the museum so plan your visit for Sunday afternoon. 

On a clear day, you can spot four states from Skydeck Chicago in the Willis Tower: Indiana, Illinois, Michigan and Wisconsin.

EAT: For lunch make your way to Lou Malnati’s Pizzeria. As a native New Yorker, it pains me to suggest deep-dish pizza, but Chicago pies really are delicious. Order the Lou pizza and inhale a slice packed with spinach, mushrooms and fresh tomatoes. Make sure you have silverware on hand because you’re going to need it!

For on-the-go bites check out Glazed and Infused, a Chicago-based gourmet doughnut shop with out-of-the-box flavors such as maple-bacon and red velvet. Or, if you’re on Clark Street, make a pit stop at the Weiner Circle for a Chicago-style hot dog. 

Finally, find out what all the buzz is about at Eataly Chicago. Step into an energetic Italian marketplace with endless grocery aisles and more than 20 different restaurants. Sign up for cooking classes or purchase edible holiday gifts for folks back home.  

Editor Kaitlyn Cimino spends more weekends away than at home but loves every minute of visiting old friends and new places.