Little Italy Holidays
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Price found within the past 48 hours. Click for updated prices.
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.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
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
€135
2 Nov - 3 Nov
includes taxes & fees
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
€176
3 Nov - 4 Nov
includes taxes & fees
8.8/10 Excellent! (5,499 reviews)
"My hotel room door was left open and unlatched the entire day. I came back to see my door unlocked, and open for anyone to go in. This was a huge safety issue, thankfully it doesn’t seem like anything was stolen. However I am hesitant to stay here again. Also, the air conditioner was very loud, and ..."
Reviewed on 8 Oct 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
€151
2 Nov - 3 Nov
includes taxes & fees
8/10 Very good! (2,437 reviews)
"Where do I start: It all started on entry, I’m 71 years old and there was no one to help me with my heavy bags up the entry stairs, no doorman, someone sitting there offering valet parking. I thank the kind gentleman who was a guest at the hotel for his assistance with my bags when he saw me struggling. ..."
Reviewed on 8 Oct 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 €1,141. 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.
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 entertainment choices 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 acclaimed art galleries.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.