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Top Holiday Package Deals in Chicago

Chicago Holiday Packages for 4 Nights

Chicago Holiday Packages for 5 Nights

Chicago Holiday Packages for 6-7 Nights

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

Hilton Chicago O'Hare Airport
Hilton Chicago O'Hare Airport
4.0 out of 5.0 Ohare International Airport, Chicago, IL
Free Cancellation
AU$179
4.0/5 (1 reviews)

The Hilton is conveniently close to the airport, accessed via tunnels. I could leave my luggage in storage for free and the train station is very close in the access tunnel so I could catch the L train downtown to fill in time until my flights left in the evening. The hotel is clean and quiet considering ...

Reviewed on 24 Oct. 2017
Located in Chicago (O'Hare), Hilton Chicago O'Hare Airport is within a 10-minute drive of Donald E. Stephens Convention Center and Rivers Casino.
Hyatt Regency Chicago
Hyatt Regency Chicago
4.0 out of 5.0 151 East Wacker Dr, Chicago, IL
Free Cancellation
AU$195
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.
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4.0 out of 5.0 701 North Michigan Avenue, Chicago, IL
Free Cancellation
AU$148
A stay at Warwick Allerton - Chicago places you in the heart of Chicago, steps from Michigan Avenue and Northwestern Memorial Hospital.
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5.0 323 E Wacker Dr, Chicago, IL
Free Cancellation
AU$164
With a stay at Swissotel - Chicago, you'll be centrally located in Chicago, within a 5-minute walk of Chicago Riverwalk and Michigan Avenue.
Radisson Blu Aqua Hotel Chicago
Radisson Blu Aqua Hotel Chicago
4.5 out of 5.0 221 N Columbus Dr, Chicago, IL
Free Cancellation
AU$224
With a stay at Radisson Blu Aqua Hotel Chicago, you'll be centrally located in Chicago, steps from Chicago Riverwalk and 4 minutes by foot from Grant Park.
La Quinta Inn & Suites by Wyndham Chicago Downtown
La Quinta Inn & Suites by Wyndham Chicago Downtown
3.0 out of 5.0 1 S Franklin Street, Chicago, IL
Free Cancellation
AU$145
With a stay at La Quinta Inn & Suites by Wyndham Chicago Downtown, you'll be centrally located in Chicago, within a 5-minute walk of Willis Tower and Skydeck ...

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.