16. Shop til you drop at Illinois’ largest mall

Woodfield Mall, located in the northwest suburbs, is one of the largest malls in the US. I love shopping here during the holiday season because I have access to a wide range of both high end and casual shops. In addition, there are a number of other shopping and entertainment options in Schaumburg: the perfect area for a full day shopping spree!

Address: 5 Woodfield Ctr. Schaumburg, IL 60173

17. Order some deep dish pizza from Giordano’s

New York vs.Chicago: who has the better pizza? It depends on your preference for thick or thin crust pizza. Deep tissue pizza lovers will be more than satisfied with the numerous Chicago pizzerias serving up the popular dish. Giordano’s is one of the most popular restaurant chains the area, with locations throughout the city and suburbs. Search for your nearest location on the Giordano’s website.

18. Enjoy a festive night at Brookfield Zoo’s Holiday Magic celebration

Dolphin show at Brookfield Zoo in Chicago

Brookfield Zoo, located just 20 minutes outside of the city, is home to one of the biggest and best zoos in the country. There are many wonderful exhibits here: a fantastic underwater polar bear viewing area, a great dolphin show, and an indoor primate area are a few of the top sights to check out. The Holiday Magic light spectacular is when the zoo really shines. Here you will be treated to a winter wonderland, complete with over a million dazzling LED lights. Caroling, Santa visits, special holiday treats, and ice carvings round out a memorable holiday evening out.

19. Visit Macy’s on State Street

Macy's holiday windows - Chicago, IL

I never leave Chicago without visiting Macy’s on State Street. I can’t leave without grabbing a box of those delicious Frango mints (which by the way are far better than Fannie Mae!) The holiday season is not complete without seeing the iconic holiday window displays and decor of the Walnut Room. The Walnut Room, located on the 7th floor, is one of Chicago’s most famous restaurants, and a must during the festive holiday season. Although Macy’s is still a holiday tradition, any loyal Chicago resident still prefers the old Marshall Field’s.

Address: 111 N. State Street Chicago, IL

20. Take a horse drawn carriage ride downtown

Scenic horse drawn carriage rides which travel the streets of downtown Chicago operate year-round, however, taking a ride during the holiday season, surrounded by all the lights, makes for a far more memorable (and romantic) experience. A romantic ride along Chicago’s scenic Magnificent Mile is the perfect way to surprise your date! Visit the Chicago Horse & Carriage website for information on operating times and prices.

Address: 806 N. Michigan Ave. Chicago, IL 60610

21. See a holiday classic at the historic Tivoli Theater

Tivoli Theater, located in suburban Downer’s Grove, is a beautiful downtown restored historic theater. Various holiday classics such as “A Christmas Story” “Christmas Vacation” and “White Christmas” show during the holiday season. Arrive early to participate in a sing along with the Wurlitzer Theater Pipe Organ.

We recently went to a showing of “Christmas Vacation.” What a fantastic experience, especially with the old time feeling and red curtains! The classic decor, red velvet seats, and beautiful holiday decor add to the ambiance.

Address: 5201 Highland Ave. Downers Grove, IL 60515

22. Take unique pictures by the Cloud Gate sculpture

Cloud gate at Millennium Park in Chicago

Referred to as “the Bean” by locals, Millennium Park’s popular Cloud Gate sculpture is a fun spot to take pictures, due to the reflective nature of the sculpture. This artistic beauty really stands out, especially with the beautiful cityscape in the background. Every tourist should plan for a viewing of this masterpiece! I recommend visiting as early in the day as possible to enjoy fantastic photographs without all the crowds!

Address: 201 E. Randolph St. Chicago, IL 60601

23. Stroll downtown Naperville

Naperville is home to one of the most charming downtowns in the Chicagoland area. The quaint downtown neighborhood features a variety of upscale shops, restaurants, and attractions. Strolling around this small section of town is a great option anytime of the year, even during the winter season. If you get cold, stop in the one of the area’s many coffee or tea shops: David’s Tea and Adagio Tea are both excellent choices.

The winter season is the perfect time to check out a new restaurant. Although there are many to choose amongst, La Sorella di Francesca really stands out.  This charming Italian restaurant features the most delicious Italian dishes, a lively atmosphere, and unique decor.

24. Go shopping at Oakbrook Center, one of the state’s nicest outdoor shopping centers

This beautiful, upscale shopping center in the Chicago suburbs is a delight during the holiday season.  Plenty of lights and a large Christmas tree light up the dark winter nights. Plenty of great anchor stores, such as Neiman Marcus, Nordstroms, Macy’s, and Lord & Taylor call Oakbrook Center home.

Maggiano’s is an excellent choice for those craving great Italian in a nice setting. I’m not a McDonald’s fan, however, fans will appreciate the modern look of this location. This McDonald’s is fanciest I have ever set foot in; here you will find a Wi-Fi center, a modern fireplace, flat screen TVs, and an overall urban design scheme.

Address: 100 Oakbrook Center Oakbrook IL 60523

25. Enjoy a tasty treat at Sprinkles Cupcakes

Sprinkles is a fantastic specialty cupcake shop with a handful of locations across the US, including one in downtown Chicago. Dozens of different flavors are available, including gluten free and vegan varieties. The Red Velvet is absolutely delicious!

Address: 50 E. Walton St. Chicago, IL 60611

26. Go ice skating at the John Hancock Observatory

John Hancock Observatory in Chicago, Illinois

The John Hancock is an amazing architectural wonder. Although most famous for the grand views of the city from its’ observatory, it is also home to the highest ice rink in the world! Take the opportunity to skate 1000 feet in the air on the 94th floor of this iconic landmark, while taking in to die for views of the city. The skating season typically starts in early January and ends in April. Visit the John Hancock website for information regarding dates and prices. To save some money on pricey skate rentals, bring you own skates that you can use over and over again.

Address: 875 N. Michigan Ave. Chicago, IL 60611