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
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 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$196 per night from 11 Nov to 12 Nov
AU$196
11 Nov - 12 Nov
includes taxes & fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$226 per night from 10 Nov to 11 Nov
AU$226
10 Nov - 11 Nov
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
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$196 per night from 23 Nov to 24 Nov
AU$196
23 Nov - 24 Nov
includes taxes & fees
8.8/10 Excellent! (5,570 reviews)
"The rooms need a deep clean, they were clean but stained on the ceiling and carpets. Bed was very worn. Staff were all very nice, from check in to seeing staff in the elevator!"

Reviewed on 29 Oct 2026

River Hotel
See all 4,749 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
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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.

Stay near popular Little Italy attractions

University of Illinois Chicago

8.4/10 (1,058 reviews)
Enjoy the student vibe at University of Illinois Chicago during your visit to Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.
See properties

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$35
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

AU$58
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

AU$61
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
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.