Chicago Vacation Deals

Absolutely! As the largest city in the Midwest, Chicago is jam-packed with fun things to keep the little ones amused. From museums to parks, zoos and even a beach. Lake Michigan is a beautiful backdrop for water-related activities.

Chicago is also known as the Windy City, so a light windbreaker jacket will serve you well alongside comfortable walking shoes. The rest of your packing list will depend largely on what time of year you plan to travel – there’s no point in packing hand warmers if you’re planning a summer vacation, right?

This is the fun part, deciding where to go and what to do! Chicago has all of the attractions you could expect from a cosmopolitan city – museums, public art, restaurants, parks and even a zoo! The hardest part will be trying to narrow it down but thankfully; plenty of Chicago’s attractions are centred in the downtown area.

Life happens - we get it! Read more here.

Chicago is generally considered a safe vacation destination for visitors young, old and in between. If you’ve got little ones in tow, stick to the downtown area as it’s the main hub for the city’s attractions and offers plenty of accommodation options.

The best time to visit Chicago is from April to May and between September and October. The summer months tend to be a little more crowded (and steamy) while winter in Chicago has a reputation for being unforgiving and frosty. That said, there’s something pretty magical about Christmas in Chicago.

Check out Millennium Park, home to The Bean (if you know, you know), get up close with penguins at the Lincoln Park Zoo, wander the Navy Pier, get a new perspective on the Centennial Wheel or the Chicago 360 Observation Deck, ride the TILT, shop Magnificent Mile, devour your body weight in Chicago’s legendary deep-dish pizza, take a free guided tour of the city, the options are endless!

Sign up to get the hottest deals sent straight to your phone & emails here. You can also check out our deals online, or speak to one of our Travel Experts.