Little Italy Holidays from AU$2,032

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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.
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
1 Apr - 8 Apr
found 6 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,253 reviews)
Great people and great place

Reviewed on 8 Jan. 2025

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
1 Apr - 8 Apr
found 6 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
We liked how attentive thw staff was. My date had a tag still attatched to him that we missed while heading out for brunch and shopping and the gentleman at the desk waived him over and let him know. Paid attention to the guest. We will definitely be back. Great staff

Reviewed on 6 Jan. 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
1 Apr - 8 Apr
found 6 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,469 reviews)
The view for the fireworks was amazing! I didn't like the fact that my wife and I both woke up with some kind of bug bites on our lower legs and on top of our feet!

Reviewed on 7 Jan. 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
1 Apr - 8 Apr
found 6 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (279 reviews)
Besides hallways being loud and like frat house from 1 to 3am , the police showing up it was very great

Reviewed on 6 Jan. 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
1 Apr - 8 Apr
found 6 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (954 reviews)
Great staff ! Friendly and I felt safe. There were staff greeting people at all times. Thx for fun!

Reviewed on 7 Jan. 2025

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 featuring a city

Downtown Chicago

5 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Millennium Park are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotel + flight trips 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$176 per night from 11 Jan to 12 Jan
AU$176
includes taxes & fees
11 Jan - 12 Jan
7.8/10 Good! (8,359 reviews)
"Loved the history of the hotel. accessible to everything"

Reviewed on 8 Jan. 2025

Congress Plaza Hotel
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$181 per night from 16 Jan to 17 Jan
AU$181
includes taxes & fees
16 Jan - 17 Jan
8.6/10 Excellent! (3,687 reviews)
"The hotel is nice and located in a beautiful setting.."

Reviewed on 9 Jan. 2025

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$177 per night from 10 Feb to 11 Feb
AU$177
includes taxes & fees
10 Feb - 11 Feb
8.6/10 Excellent! (2,793 reviews)
"I think this is a great place! This was my second time staying there. Although, I do feel that parking prices/services could be explained a little better by their staff. Other than that, the room and stay was lovely."

Reviewed on 6 Jan. 2025

Eurostars Magnificent Mile
See all 3,692 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Little Italy holiday package cost?
From as little as AU$2,032. 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.

Discover the most popular places to visit in Little Italy

University of Illinois Chicago

University of Illinois Chicago

4.5/5(4 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.

University of Illinois Chicago

Activities

Chicago Hauntings Original Ghost Bus Tour

Chicago Hauntings Original Ghost Bus Tour

AU$95
per adult
Chicago Hauntings Original Ghost Bus Tour
Flyover in Chicago

Flyover in Chicago

AU$61
per adult
96% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

AU$79
per adult
94% of travellers recommend
Architecture River Tour
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.