Chicago Holiday Deals

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

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.

Things to Do in Chicago

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 lastminute.com.au 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”.

Top hotels for your Chicago holiday

River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$186 per night from 31 Mar to 1 Apr
AU$186
per night
31 Mar - 1 Apr
With a stay at River Hotel, you'll be centrally located in Chicago, steps from Michigan Avenue and 5 minutes by foot from Chicago Riverwalk.
"Great customer service"

Reviewed on 27 Mar. 2024

River Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$169 per night from 31 Mar to 1 Apr
AU$169
per night
31 Mar - 1 Apr
With a stay at Club Quarters Hotel, Central Loop, Chicago, you'll be centrally located in Chicago, just a 5-minute walk from Willis Tower and 7 minutes by foot ...
"I’ve stayed here many times and have never been disappointed."

Reviewed on 25 Mar. 2024

Club Quarters Hotel, Central Loop, Chicago
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$193 per night from 1 Apr to 2 Apr
AU$193
per night
1 Apr - 2 Apr
With a stay at Congress Plaza Hotel, you'll be centrally located in Chicago, steps from Columbia College Chicago and Museum of Contemporary Photography.
"Loved our lake view room"

Reviewed on 27 Mar. 2024

Congress Plaza 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.

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^Savings based on all package bookings made with Flight + Hotel on lastminute.com.au 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.