Chicago Holiday Deals

About Chicago

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Frequently asked questions

Is Chicago a good place for a family vacation?

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.


What to take on holiday to Chicago?

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?


Where to go on holiday in Chicago?

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.


How do I go about cancelling my Chicago holiday package?

Life happens - we get it! Read more here.


Is it safe to take kids to Chicago?

Chicago is generally considered a safe holiday 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.


When is the best time to visit Chicago?

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.


What is there to do 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!


How to find the best holiday package to Chicago?

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.


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*Travel restrictions & conditions apply. Prices & taxes are in NZD and are correct as at the date of publication & are subject to availability and change without notice. Prices quoted are on sale until the dates specified unless otherwise stated or sold out prior. Prices are per package. We charge a Travel Expert Service Fee for bookings made with our travel experts in store, via email or over the phone and an Online Booking Fee for flight bookings made online. These fees are charged in addition to the advertised price and displayed fares. Merchant fees apply and depend on your chosen payment method. View Booking Terms and Conditions for more information.