Ultimate Chicagoland Winter Travel Guide

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After three years traveling the globe, Harry and I returned to our hometown of Chicago for the holidays. In between visiting our friends and family, we toured around the city with fresh, new eyes. Our goal was to create a winter guide showcasing the best of Chicagoland. Come check out some great ways to spend these cold, dreary days in and around the Windy City.

24 HOURS IN CHICAGO: WINTER IN THE WINDY CITY

Our goal was to showcase a fun, festive day exploring Chicago to inspire our friends and followers from around the globe to visit our hometown city. We spent a lovely day together during the height of the Christmas season. Come check out some of Chicago’s best stops on our tour of downtown.

SPICE UP DATE NIGHT AT THE CHOPPING BLOCK

As part of quest to find the best holiday-inspired events in Chicagoland, we signed up for The Chopping Block‘s “Eat, Drink, & Be Merry” cooking class. We ended up having such a great date night that we were inspired to share more about our culinary adventure in Chicago’s charming Lincoln Square neighborhood.

CRUISE ABOARD THE ODYSSEY

Many may not think of heading out on Lake Michigan during the winter months, but we had a fabulous time aboard The Odyssey on a Saturday night in December. At this time of the year, everyone seems to be organizing holiday gatherings, social get-togethers, and special events. With our recent arrival back to Chicago, a group of us were looking for a fun night out on the town. We contacted the folks at Entertainment Cruises for a night to remember.

CHICAGO’S BEST HOLIDAY TOUR

We were warmly invited to kick off the holiday season in the city on the Chicago Trolley Holiday Lights Tour. Since 1994, Chicago Trolley & Double Decker Company has been providing guests unique transportation throughout the Chicagoland area, Illinois, Indiana, and Wisconsin. As the original trolley tour in the city, it’s an established Chicagoland tradition!

BROOKFIELD ZOO HOLIDAY MAGIC

One of Chicagoland’s most beloved winter attractions is Holiday Magic at Chicago’s Brookfield Zoo. Families have been visiting the zoo to enjoy the light displays for over 36 years. This is Chicago’s largest and longest running light festival.

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