Little Italy Holidays

Book a Hotel + Flight or Car together to unlock savings

    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to NZ$545 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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 Navy Pier 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

River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$219 per night from 27 Oct to 28 Oct
NZ$219
per night
27 Oct - 28 Oct
8.6/10 Excellent! (3,415 reviews)
"Great Walkability. Close to shoping, river walk, restaurants, museums, theaters, etc. The rooms are small and good enough. Nothing special. But I would recommend to buy snacks and drinks for your room, there is no hotel shop."

Reviewed on 24 Sep. 2024

River Hotel
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 NZ$252 per night from 1 Oct to 2 Oct
NZ$252
per night
1 Oct - 2 Oct
7.6/10 Good! (7,860 reviews)
"I loved the lake view from the room, the classic feel of the property, and the super helpful and friendly staff!"

Reviewed on 24 Sep. 2024

Congress Plaza 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 NZ$334 per night from 27 Oct to 28 Oct
NZ$334
per night
27 Oct - 28 Oct
8.6/10 Excellent! (2,577 reviews)
"It was very clean and nice. The gym was very underwhelming but that's really it."

Reviewed on 24 Sep. 2024

Eurostars Magnificent Mile
See all 3,860 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.

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

Image for 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 acclaimed art galleries in this vibrant area.

University of Illinois Chicago
Image for Credit Union 1 Arena

Credit Union 1 Arena

Catch an event at Credit Union 1 Arena during your trip to Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.

Credit Union 1 Arena
Image for Jane Addams' Hull-House Museum

Jane Addams' Hull-House Museum

You can enjoy some culture when you stop by Jane Addams' Hull-House Museum in Chicago. Discover the acclaimed theatre scene and notable monuments in this vibrant area.

Jane Addams' Hull-House Museum

Activities

Image for Chicago Hauntings Original Ghost Bus Tour

Chicago Hauntings Original Ghost Bus Tour

NZ$72
Per adult
Chicago Hauntings Original Ghost Bus Tour
Image for Flyover in Chicago

Flyover in Chicago

NZ$45
Per adult
96% of travellers recommend
Flyover in Chicago
Image for Architecture River Tour from Navy Pier

Architecture River Tour from Navy Pier

NZ$87
Per adult
94% of travellers recommend
Architecture River Tour from Navy Pier
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.