Little Italy Holidays

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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 hotels in Downtown Chicago

Top hotels in Little Italy

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 S$267 per night from 4 Aug to 5 Aug
S$267
4 Aug - 5 Aug
includes taxes & fees
7.8/10 Good! (8,942 reviews)
"It was perfect for my family. Very close to the millennium Park"

Reviewed on 12 Jul, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is S$340 per night from 10 Aug to 11 Aug
S$340
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (2,036 reviews)
Gorgeous and friendly
"Gorgeous hotel! Friendly staff, especially the door men were so helpful and fun. Had a small leak dripping water by the entrance of our room but they got it fixed in a timely manner."

Reviewed on 13 Jul, 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$227 per night from 10 Aug to 11 Aug
S$227
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (2,431 reviews)
"Good experience! Not the best but not bad, a little pricey for the quality and service offered"

Reviewed on 12 Jul, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,560 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.

Popular places to visit

University of Illinois Chicago

University of Illinois Chicago

4.5/5(11 reviews)

Enjoy the student vibe at University of Illinois Chicago during your visit to Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area.

University of Illinois Chicago

Things to do

Chicago Hauntings Original Ghost Bus Tour

Chicago Hauntings Original Ghost Bus Tour

S$75
per adult
Chicago Hauntings Original Ghost Bus Tour
Boystown (North Halsted) - Boystown

Tour Chicago LGBTQ Style: On and Off History Bus Tour

S$64
per adult
Tour Chicago LGBTQ Style: On and Off History Bus Tour
River tour boat in Chicago

Architecture River Tour

S$53
per adult
96% of travellers recommend
Architecture River Tour
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.