Chicago Holiday Deals

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Things to Do in Chicago

Holiday In Chicago

When you’re trying to blow out of town, catch the next big gust to the “Windy City”. Known for its bustling riverfront venues, a lively arts scene and Midwestern gumption, no one can accuse “Chi-town” of actually being shy. If you want to kick it on the banks of enormous Lake Michigan, you’ll be welcomed with open arms. But before embarking on holidays to Chicago, Illinois, you should know that natives are serious about a few things: Deep-dish pizza, professional sports and making you laugh your arse off. As it happens, we’re serious about those, too.

Chicago holidays are all about history and shouting baseball fans. Hit two balls with one bat at Wrigley Field, built in 1914. Once you’ve caught a pop fly and eaten your share of ball park wieners, chill out in Millennium Park in the famous Chicago Loop. From that prime location, you’ll be within walking distance to popular activities, like the Art Institute of Chicago, Chicago Cultural Center and the Cloud Gate sculpture. Sure, that last bit is a bean-shaped art installation, but add planking and people-watching and you’ll have pure social media gold. Now, if there’s one thing you’ve got to do on your Chicago holiday, it’s amble around the Chicago Riverwalk. Tuck into the many cafes and shops or head to Navy Pier for carnival rides—no boot camp required. Public transit is stellar around the city centre, but check out our fantastic Chicago car hire options to ease your commute to Lincoln Park Zoo or the ballpark.

Shopping, Dining & Nightlife

They don’t call North Michigan Avenue the “Magnificent Mile” for nothin’. This street is lined with some of the best shopping haunts near the Great Lakes. Don’t know where those are? Look eastward. You can easily watch the dollars turn into designer clothes, so it’s a good thing you’re about to save on our great Chicago packages. Just saying. For one-of-a kind finds, follow the current trends to River North, Chi-town’s largest arts district.

Ask any Chicagoan where to find the best deep-dish pizza—you’ll get a different story from everyone. That just means you need to try them all! Between saucy slices, remember that Chicago is an international city, and you can stay in neighbourhoods based on the eats you plan to devour. Graze on chicken Vesuvio in Little Italy or find ma po tofu by the bowl in Chinatown. This flavourful favourite is served all over the city, just in case the craving strikes.

In Chicago, you’re ether feeling the blues or laughing till you cry. Considered “The World Capital of the Blues”, this lakeside destination can croon along with the greats like Muddy Waters and Koko Taylor. Speaking of greats, comedians Bill Murray, Tina Fey and many others got their starts at The Second City Theatre, a comedy club that’s been LOL-ing in Old Town since 1959.

What’s Next?

If we lost you at “deep-dish pizza”, we’ll keep it simple. Book Chicago holiday packages with for the best deals on your choice of airfares and accommodation. If you can’t get enough of this Midwestern gem, book sweet Illinois holiday deals and roll through “The Prairie State”.

Hotels in Chicago

Your perfect Chicago hotel awaits on At present, there are 165 digs to pick from.

Who said that service with a smile needs to cost an arm and a leg? You'll have a relaxing night's sleep at a nice price at the Old Chicago Inn and the Urban Holiday Lofts. But then again — you are on holiday. If you'd rather live large while you're here, we certainly don't blame you! The experienced staff at the Waldorf Astoria Chicago and The Peninsula Chicago are specialists in luxury.

Like the idea of booking a place closer to the Art Institute of Chicago? The Langham, Chicago and the JW Marriott Chicago are both within a short walking distance of this world-famous sight.

Top hotels for your Chicago holiday

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
300 E Ohio St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$234 per night from 31 Oct. to 31 Oct.
With a stay at DoubleTree by Hilton Chicago - Magnificent Mile in Chicago (Near North Side), you'll be within a 5-minute walk of Michigan Avenue and Prentice ...
DoubleTree by Hilton Chicago - Magnificent Mile
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$158 per night from 7 Nov. to 7 Nov.
With a stay at Congress Plaza Hotel, you'll be centrally located in Chicago, steps from Columbia College Chicago and Museum of Contemporary Photography.
Congress Plaza Hotel
The Whitehall Hotel

The Whitehall Hotel

4 out of 5
105 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$143 per night from 8 Nov. to 8 Nov.
A stay at The Whitehall Hotel places you in the heart of Chicago, steps from Michigan Avenue and State Street.
The Whitehall Hotel
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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.

^Savings based on all package bookings made with Flight + Hotel on from January 1, 2019 to December 31, 2019, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.