Little Italy Holidays from AU$1,499

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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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was AU$1,845, price is now AU$1,499 per person
AU$1,499
per person
29 May - 1 June
found 5 hours ago
Return flight included
Los Angeles (LAX) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great and helpful staff very clean, a place where you don’t feel out of place

Reviewed on 25 Apr 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$2,866, price is now AU$2,025 per person
AU$2,025
per person
29 May - 1 June
found 5 hours ago
Return flight included
Los Angeles (LAX) to Chicago (ORD)
9.2/10 Wonderful! (946 reviews)
Rooms were cleaned I liked how secure the hotel was.

Reviewed on 29 Apr 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$2,433, price is now AU$1,733 per person
AU$1,733
per person
29 May - 1 June
found 5 hours ago
Return flight included
Los Angeles (LAX) to Chicago (ORD)
9.4/10 Exceptional! (2,458 reviews)
We were there for a wedding and didn't have time for much else.

Reviewed on 26 Apr 2026

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$2,836, price is now AU$2,129 per person
AU$2,129
per person
29 May - 1 June
found 5 hours ago
Return flight included
Los Angeles (LAX) to Chicago (ORD)
9.2/10 Wonderful! (3,002 reviews)
Welcoming, accommodating, pampering and regenerating experience every time we stay at the Intercontinental. A wonderful place to enhance one’s Chicago experience.

Reviewed on 29 Apr 2026

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$2,083, price is now AU$1,689 per person
AU$1,689
per person
29 May - 1 June
found 5 hours ago
Return flight included
Los Angeles (LAX) to Chicago (ORD)
8.8/10 Excellent! (2,177 reviews)
Only one working elevator… furniture in the room was chipped & headboard was damaged or dirty we could not determine… Overall location is good… staff is awesome.. but the price paid through Tpa was not worth it.. the medicine room and maintenance of the room & furniture..

Reviewed on 28 Apr 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

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

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$186 per night from 25 May to 26 May
AU$186
25 May - 26 May
includes taxes & fees
8.2/10 Very Good! (2,646 reviews)
Great location nice hotel!

Reviewed on 28 Apr 2026

Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is AU$238 per night from 25 May to 26 May
AU$238
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (5,134 reviews)
Beautiful, clean room with an incredible downtown Chicago view. Totally worth it

Reviewed on 29 Apr 2026

River Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$182 per night from 25 May to 26 May
AU$182
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (3,478 reviews)
Great check in and check out experience

Reviewed on 29 Apr 2026

Club Quarters Hotel, Central Loop, Chicago
See all 4,775 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$1,499. 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

Tri Taylor

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 acclaimed theatre scene in this vibrant area.

University of Illinois Chicago

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$38
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

AU$61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

AU$56
per adult
92% of travellers recommend
Art Institute of Chicago
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.