41. Grab a hot chocolate and window shop downtown


The winter setting is perfect for a stroll around downtown: beautiful lights and decor, horse & carriage rides, special holiday markets, and more. Another bonus comes with the quieter atmosphere: peace and quiet! There is such a drastic difference between crowds in the winter vs. summer months. I try to get out and ice skate at Millennium on a weekday morning/afternoon for the fewest crowds as insane lines often form quickly on the weekends!

42. Explore unique space exhibits at the Adler Planetarium

The Adler is one of the premier planetariums in the country. Interesting space exhibits and incredible shows in The Grainger Sky Theater provide for a full day of learning and fun! Afterwards, be sure to snap a bunch of pictures outside. The planetarium patio is the absolute best spot in the city for skyline photography (the cover photo was taken here!).

Address: 1300 South Lake Shore Drive Chicago, IL 60605

43.Get lucky at the slots on the Grand Victorian in Elgin, IL

In addition to Hollywood Casino, your other option for riverfront casinos in the Chicago suburbs is the Grand Victorian, located approximately 45 minutes from Chicago. Various table games and slots are offered. In addition, you will find numerous dining and entertainment options, including a popular buffet.

Address: 250 S. Grove Ave. Elgin, IL 60120

44. Enjoy a relaxing escape at Lake Katherine


Lake Katherine is a beautiful, small 85 acre park in the Chicago suburbs. It’s a great alternative to shopping and dining. Pick a warmer winter day, bundle up, and enjoy the quaint views of the lake, woods, and waterfall. A little bit of light exercise will brighten your mood during the bleak, long winter months.

Address: 7402 Lake Katherine Drive, Palos Heights, IL 60463

45. Find a local park to go cross country skiing or snowshoeing


Not only are cross country skiing and snowshoeing incredibly fun winter activities, they burn a lot of calories! Did you know that cross country skiing is one of the top cardio activities, right behind running and basketball?! To me, there is nothing that says winter more than getting out to a snowy park and skiing in the serene winter setting. To find a park that offers cross country skiing, visit the Chicago Parks District website. Tip: I recommend purchasing your own pair of snowshoes. Rentals can get quite pricey, especially if you plan on making snowshoeing a regular winter activity.

46. Take a self guided tour of movie filming locations

Many classics such as The Breakfast Club, Home Alone, Sixteen Candles, My Best Friends Wedding, Ferris Bueller and more have filmed in various locations in and around the city. Why not take a tour of all your favorite films from the 80’s or 90’s? An entertaining and free activity to perk up the boring winter season!

Address: It’s Filmed There website lists all the addresses for these movies and more.

47. Volunteer at the McDonald’s Thanksgiving Parade

Although not as iconic as New York’s popular Macy’s Thanksgiving Day Parade, this festive Chicago parade still holds its’ own. What better way to be a part of all the action then volunteering to carry one of the balloons down historic State Street?

Mike & I had a blast several years ago, and would love the opportunity to take part in this fantastic event again. Mark your calendars – this year’s parade will air on November 27th, from 8:00-11:00am on WGN. Visit the Chicago Festivals website for a volunteer application, along with additional information on the parade.

Address: State Street (Congress to Randolph)

48. Treat yourself to a delicious breakfast at Wildberry

Wildberry Chicago

Wildberry, an outstanding restaurant located in Chicago’s downtown on Randolph St., serves up an enticing breakfast menu. You will find specialty pancakes (S’mores, tiramisu, gluten free Honey-Cakes, etc), French toast creations, omelettes, and more! Service is outstanding, prices are affordable, and the location can’t be beat (Millennium Park).

Address: 130 E. Randolph St. Chicago, IL 60601

49. Holiday shop at Orland Square

I have been to a lot of malls throughout the country, but I always come back to fantastic Orland Square Mall! There is just something about this mall around the holidays that make it perfect – the cheerful atmosphere, nice layout, variety of shops, and festive decor make it the ideal suburban stop for all your holiday shopping.

You don’t have to stop with the mall as Orland Park is home to some of the best shopping in the Southwest suburbs. Here you will find dozens of strip malls, complete with any store you can imagine. Don’t worry, there are plenty of restaurants in the area if you need to take a break from the crowds. Papa Joe’s is a great casual, local Italian choice.

Address: 288 Orland Square Drive Orland Park, IL 60462

50. Find a local park district ice rink

Most neighborhood rinks are free to skate, and only charge a few dollars or so for skate rentals.One of my favorite suburban rinks is Orland Park’s Winter Wonderland ice rink, located at Centennial Park. The rink is large, almost never crowded, and provides a quiet park like setting. As a bonus, skate rentals are only $2! Visit The Orland Park website for information on this season’s operating dates and times.

Address: 15600 West Ave. Orland Park, IL 60462

Just for Fun

And just for fun, here are some of my favorite gift ideas for Chicago lovers.

11 Chicago Themed Gifts for Christmas, Birthdays, Etc.

MLB Chicago Cubs Fleece Blanket – The perfect winter gift for Cubs fan. Keep cozy all season long!

Chicago-Opoly – A fun monopoly style game for residents and locals! I received this as a Christmas gift and I just love it!

Chicago snowglobe – Anyone who collects snowglobes will love this one which includes a replica of the Chicago skyline. It makes a great Christmas gift!

Chicago Canvas wall decor – You really can’t go wrong with a classic picture of the Chicago skyline. Absolutely beautiful and perfect for locals and visitors who love the city.

Michigan Avenue puzzle – For any puzzle fans out there, this 1000 piece puzzle is really hard and will take forever to complete – but that’s just part of the fun! A beautiful photo of Michigan awaits you upon your completion. This 4D Chicago puzzle is pretty cool as well.

Kurt Adler Chicago Christmas Ornament – This beautiful glass Chicago skyline ornament is the perfect addition to your Christmas tree. Also makes a great stocking stuffer or gift idea for any Chicago lovers you know.

NFL Chicago Bears tumbler – This travel tumbler is really the perfect gift for any Chicago Bears fan. I bought it for my bf last Christmas and he loves to bring it with on any road trip!

Chicago Bears Christmas ornament – LOL this gift is just perfect for the die hard Chicago Bears fan just hoping to someday see their team in the Superbowl again!

Chicago Bears winter hat – Fashionable and functional at the same time – you’ll need it this winter!

Chicago Bears nutcracker – I received this as a stocking stuffer years back and I still display it every year! Great gift idea for football fans!

Chicago wine glass – I just love the line of Lolita hand painted wine glass. If you have ever been in a Hallmark store, you have probably seen them too. This Chicago themed version, featuring memorable sights such as Wrigley Field, Michigan Ave, and Navy Pier is the perfect novelty gift idea!