Little Italy Holidays from AU$3,449

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Your Little Italy Holiday

A well-liked food-lovers neighbourhood, Little Italy tempts visitors with its cafes, markets and bars and pubs. Lock in a holiday package to Little Italy and look forward to experiencing all of those highlights and more. Kick off your trip to Little Italy by checking out nearby attractions such as University of Illinois Chicago, United Centre and Anna and Frederick Douglass Park. Expedia can help you turn your dream Little Italy holiday into reality, whatever your travel plans or budget.

Top Holiday Package Deals in Little Italy

Price found within the past 48 hours. Click for updated prices.
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Downtown Chicago
Price was AU$3,666, price is now AU$3,449 per person
AU$3,449
per person
1 Aug - 3 Aug
found 3 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
8.8/10 Excellent! (2,257 reviews)
The room size, location, and comfortable bed were excellent.

Reviewed on 8 June 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was AU$4,089, price is now AU$3,701 per person
AU$3,701
per person
1 Aug - 3 Aug
found 3 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
The fitness center & spa was top notch. The on site restaurant had amazing food and service.

Reviewed on 12 June 2026

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was AU$3,733, price is now AU$3,466 per person
AU$3,466
per person
1 Aug - 3 Aug
found 3 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
We were booked at The wit. We weren’t checking in until later (9pm) so I called around 5pm to see if they could make a note in my reservation that we were a late check in & to not give the room away. They said okay. We get to the hotel around 9 & were told that our room was no longer available & they had no other available. I still give The Wit 3 stars because they were apologetic & vouchered us to a hotel next door. So, a little disappointed, but what can you do?

Reviewed on 7 June 2026

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Price was AU$3,801, price is now AU$3,578 per person
AU$3,578
per person
1 Aug - 3 Aug
found 3 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
Darnell at the front desk was so warm and helpful. Our room was as pretty and cozy as it gets, the view to die for. The restaurant downstairs has the best French toast on earth. For reals!

Reviewed on 13 June 2026

Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
Downtown Chicago
Price was AU$3,722, price is now AU$3,510 per person
AU$3,510
per person
1 Aug - 3 Aug
found 3 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
8.6/10 Excellent! (3,051 reviews)
would definitely go there again. good location. room was clean. dud not use any amenities and had no interaction with staff

Reviewed on 13 June 2026

Our guide on where to stay in Little Italy

Find the best Little Italy areas and neighborhoods for the activities you enjoy most. Learn more about Little Italy
Downtown Chicago

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Our pick of the best Little Italy Hotel Deals

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$229 per night from 29 June to 30 June
AU$229
29 June - 30 June
includes taxes & fees
8/10 Very Good! (10,264 reviews)
"Great stay!"

Reviewed on 14 June 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is AU$244 per night from 30 June to 1 July
AU$244
30 June - 1 July
includes taxes & fees
7.8/10 Good! (1,578 reviews)
"Had a great time over two days in Chicago. The only downside was that my room was not cleaned when I returned."

Reviewed on 14 June 2026

The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is AU$232 per night from 30 June to 1 July
AU$232
30 June - 1 July
includes taxes & fees
8.8/10 Excellent! (2,666 reviews)
"Overall stay was great with my brother. I will come back agin. Staff were helpful especially with our shuttle ride to the airport."

Reviewed on 13 June 2026

Hyatt Regency O'Hare Chicago
See all 4,639 properties in Little Italy
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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Frequently asked questions

How much does a Little Italy holiday package cost?
From as little as AU$3,449. Yes, you read that correctly. Our Little Italy holiday packages are a simple way to make your budget go further. Bundle your preferred hotels, flights and rental car and get out and explore this top destination.
How do I get a cheap travel package to Little Italy?
Creating your own Little Italy holiday package with Expedia is one of the easiest ways to save. We have access to more than 550 partner airlines and 1 000 000 properties across the globe. With such a fabulous range to select from, you'll have no trouble putting together your perfect adventure.
Where should I stay in Little Italy?
A journey to Little Italy isn't complete without stopping by University of Illinois Chicago and United Centre. Reserve a room within walking distance and easily access these famous sights.
What are the top hotels in Little Italy?
Whether you're staying for one night or a week in Little Italy, you'll get a good night's rest at Courtyard by Marriott Chicago at Medical District/UIC. This option is popular with plenty of travellers.
How far in advance should I book my Little Italy holiday?
Travellers are normally able to compare international airfares on Expedia within 12 months of departure. Booking late? With a little bit of luck, it's still possible to score a cheap ticket only weeks before your flight.
What does an Expedia Little Italy travel package include?
Packages include rental cars, hotels and flights, but you can mix and match them to create your dream Little Italy escape. You can also add on some activities and tours once you've made your booking. You're in control! When you combine your bookings with Expedia, you'll enjoy deals you won't find anywhere else.
What should I know before booking a Little Italy travel package?
Design deals that match your budget with an Expedia package. Hotels, airfares, rental cars — we have everything you need to plan your escape. You'll save precious cash just by bundling your bookings. Whether you're going on a snow and ski adventure or venturing someplace warm, your ideal holiday is just clicks away.
Can I choose my airline with a Little Italy Expedia holiday package?
With a holiday package, you're always in charge. Whether you're looking to fly to Little Italy in business or coach, simply choose from the available airline options. Expedia has access to more than 550 airline partners all over the world.
If I'm not able to travel, can I cancel my Little Italy holiday package?
If your holiday plans in Little Italy have been upended, it's a relief to know that it is possible to amend or cancel your booking. If you booked in the last 24 hours, you may be able to get a refund. If your booking is older than that, your airline, hotel or car rental company may charge fees. For more information, check our Customer Service Portal.

Stay near popular Little Italy attractions

University of Illinois Chicago

4.2/5 (1,058 reviews)
Enjoy the student vibe at University of Illinois Chicago during your visit to Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.