Chicago Holiday Packages

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Willis Tower featuring mist or fog, a city and city views

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Chicago Holiday Packages

Chicago, Illinois, is the perfect choice for an American holiday—it has a busy, powerful vibe similar to New York, with just as much to do and see. Chicago packages are your ticket to an American Midwest secret: “The Windy City” has some of the best food, shopping and nightlife in the U.S.—at least, according to the locals! Why not decide for yourself on your next holiday?

Things to Do in Chicago

Navy Pier is a can’t-miss activity for any holiday in Chicago. The 45m-tall Ferris wheel is sure to catch your attention take a spin for great city views. Then do your best sailor swagger into the shops, where you just might find those perfect skyline-shaped chocolates. Don’t be “a-freud” to stop and chat with the statue of TV-psychologist Bob Newhart, whose couch is designed for therapeutic confessions (and photo ops). Hungry? Travel to the tropics inside Crystal Gardens, a one-acre greenhouse with palm trees, fountains and a variety of restaurants.

If you’re in the mood for some education, or the weather just isn’t on your side, explore indoors at one of Chicago’s museums. Always wanted to see the world from an ant’s perspective or learn about man-eating lions in Kenya? The Field Museum of Natural history, one of the largest in the world, is your playground. You could also book a Chicago car hire and head north to the Illinois Railway Museum or south to the Museum of Science and Industry.

Shopping, Dining & Nightlife

The money you’ve saved with our Chicago package deals is probably burning a hole in your pocket, so it’s time to decide: What’s your shopping style? The Magnificent Mile lives up to its name, with world-famous luxury brands and posh boutiques. In the Loop neighbourhood, rock collectors can find the perfect marquise cut on Jewelers Row, while bargain hunters can dig through discount racks on State Street. A Chicago holiday near Millennium Park is the perfect home base for shopaholic getaways, with both these neighbourhoods within walking distance.

You can show off your new diamonds at dinner without even leaving Mag Mile—it’s one of the best neighbourhoods for upscale dining. However, Chicago holidays are best spent exploring go northwest to find up-and-coming Lincoln Park, filled to the brim with the vanguard of experimental cuisine. Get your hands on mozzarella balloons, inside-out eggs benedict and crispy pig’s ears, and your taste buds will never be the same.

Swanky sightseers can keep their holiday going into the wee hours in Gold Coast, an area that is, you guessed it, on the Lake Michigan coast and very exclusive. Head over to stylish Rush Street to get your groove on with live jazz, reggae or funk. For the younger (or just hipper) crowd, Wicker Park is all about trendy cocktails, groovy tunes and a laid-back vibe. Plus, it’s got a subway stop on the 24-hour Blue Line, so you can easily get back downtown without even springing for a cab.

What’s Next?

The next steps are easy—listen to your holiday self and book your getaway with Wotif. We have the best Chicago hotel packages, because you can mix and match with flights to the same destination to create your perfect escape. Check us out today.

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.