Little Italy Holidays

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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.

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

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$240 per night from 18 Aug to 19 Aug
AU$240
18 Aug - 19 Aug
includes taxes & fees
7.8/10 Good! (8,994 reviews)
"The time of lake was awesome"

Reviewed on 27 Jul. 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is AU$485 per night from 22 Aug to 23 Aug
AU$485
22 Aug - 23 Aug
includes taxes & fees
9/10 Wonderful! (2,121 reviews)
"It is very loud and a lot of people. It is a great place to stay if you are good with noise and people. It is high energy."

Reviewed on 27 Jul. 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$257 per night from 17 Aug to 18 Aug
AU$257
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (2,539 reviews)
"Was great for our family trip to Chicago."

Reviewed on 26 Jul. 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,665 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 . 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

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$90
per adult
Chicago Hauntings Original Ghost Bus Tour
Boystown (North Halsted) - Boystown

Tour Chicago LGBTQ Style: On and Off History Bus Tour

AU$76
per adult
Tour Chicago LGBTQ Style: On and Off History Bus Tour
River tour boat in Chicago

Architecture River Tour

AU$75
per adult
96% 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.