Little Italy Holidays
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Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
€603
per person
24 Sept - 29 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.4/10 Very good! (3,942 reviews)
We had a great hotel stay. Property is clean and staff is very helpful!
Reviewed on 24 Aug 2026
Swissotel - Chicago
Downtown Chicago
€854
per person
24 Sept - 29 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (3,553 reviews)
Rooms are extremely cold. Glass/ mirrors & table dirty with fingerprints & crumbs still on table. Shower leaked water all over floor. Toilet had hair on it. Not informed about hidden $30 feet a day. Did not sleep comfortably during stay due to room temperature
Reviewed on 23 Aug 2026
Silversmith Hotel Chicago Downtown
Downtown Chicago
€789
per person
24 Sept - 29 Sept
found 19 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (2,348 reviews)
A lot of junk fees parking horrible so valet 89 dollars a night hotel was clean but the area was not good for downtown homeless people everywhere restaurants close at 9 pm on weekends and traffic so bad u have to uber everywhere and valet I booked this room for 2 days for a concert wanted the best but was not the best location for 750 for 2 nights everywhere we went we had to uber their and back
Reviewed on 24 Aug 2026
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
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.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Top hotels in Little Italy
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
€117
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,304 reviews)
"Lovely stay, beautiful architecture"
Reviewed on 24 Aug 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
€146
30 Aug - 31 Aug
includes taxes & fees
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
€259
18 Sept - 19 Sept
includes taxes & fees
8.4/10 Very good! (2,436 reviews)
"Convenient location and beautiful hotel!"
Reviewed on 23 Aug 2026
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 €603. 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 acclaimed art galleries in this vibrant area.
Credit Union 1 Arena
8.0/10 (5 reviews)
Catch an event at Credit Union 1 Arena during your trip to Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area.
Jane Addams' Hull-House Museum
You can spend time studying the exhibits at Jane Addams' Hull-House Museum in Chicago. Discover the acclaimed theatre scene and notable monuments in this vibrant area.
Addams/Medill Park
After visiting Addams/Medill Park, make a plan to see the other sights and activities in Chicago. Experience the acclaimed theatre scene and entertainment choices in this vibrant area.
St. Basil Greek Orthodox Church
St. Basil Greek Orthodox Church is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its entertainment choices.
Provision Theater
You can make plans for a show at Provision Theater on your trip to Chicago. Stroll along the riverfront or experience the acclaimed art galleries in this vibrant area.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
€21
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.