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Top Holiday Package Deals 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.

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”.


Guide to Exploring Chicago


Top Hotel Deals in Chicago

The Whitehall Hotel
The Whitehall Hotel
4.0 out of 5.0 105 E Delaware Pl, Chicago, IL
Free Cancellation
AU$201
4.0/5 (3 reviews)

Hotel in excellent location. Walking distance to great stores.

Reviewed on 3 Jan. 2018
A stay at The Whitehall Hotel places you in the heart of Chicago, steps from Michigan Avenue and State Street.
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5.0 520 South Michigan Avenue, Chicago, IL
Free Cancellation
AU$235
With a stay at Congress Plaza Hotel, you'll be centrally located in Chicago, steps from Columbia College Chicago and Museum of Contemporary Photography.
Hotel Essex Chicago
Hotel Essex Chicago
4.0 out of 5.0 800 S Michigan Ave, Chicago, IL
Free Cancellation
AU$195
With a stay at Hotel Essex Chicago, you'll be centrally located in Chicago, steps from Grant Park and 9 minutes by foot from Buckingham Fountain.
Inn of Chicago
Inn of Chicago
3.0 out of 5.0 162 E Ohio St, Chicago, IL
Free Cancellation
AU$140
With a stay at Inn of Chicago, you'll be centrally located in Chicago, steps from Michigan Avenue and 4 minutes by foot from Tribune Tower.
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4.0 out of 5.0 701 North Michigan Avenue, Chicago, IL
Free Cancellation
AU$206
A stay at Warwick Allerton - Chicago places you in the heart of Chicago, steps from Michigan Avenue and Northwestern Memorial Hospital.
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4.0 out of 5.0 17 E Monroe St, Chicago, IL
Free Cancellation
AU$302
Palmer House a Hilton Hotel is in the heart of Chicago, within a 5-minute walk of Art Institute of Chicago and Millennium Park.
The St. Clair Hotel – Magnificent Mile
The St. Clair Hotel – Magnificent Mile
2.5 out of 5.0 162 East Ontario Street, Chicago, IL
Free Cancellation
AU$176
With a stay at The St. Clair Hotel – Magnificent Mile in Chicago (Near North Side), you'll be within a 5-minute drive of Grant Park and Millennium Park.
Hyatt Regency Chicago
Hyatt Regency Chicago
4.0 out of 5.0 151 East Wacker Dr, Chicago, IL
Free Cancellation
AU$345
With a stay at Hyatt Regency Chicago, you'll be centrally located in Chicago, steps from Chicago Riverwalk and within a 10-minute walk of Grant Park.

Top Deals on Flights to Chicago

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.