Little Italy Vacations from $252

Book a Hotel + Flight or Car together to unlock savings

Your Little Italy Vacation

A well-liked food-lovers neighborhood, Little Italy tempts visitors with its cafes, markets and bars and pubs. Lock in a vacation 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 Center and Anna and Frederick Douglass Park. Expedia can help you turn your dream Little Italy vacation into reality, whatever your travel plans or budget.

The Latest Little Italy Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $412, price is now $252 per person
$252
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Clean hotel and room. Front staff very good. Good location. Will stay again.

Reviewed on Dec 10, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $790, price is now $434 per person
$434
per person
Jan 30 - Feb 4
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
The rooms were great. Very spacious, fully stocked kitchen and extremely clean. We loved having access to the 8th floor with the steam room, sauna, fitness center, game rooms, and socializing areas 24/7. Would love to experience it in the summer with the pool and outdoor areas. We were also fortunate enough to attend during their Christmas Brunch buffet which was such a great perk! If the price stays around the same, I will continue to stay at Level hotels exclusively in any cities I visit that has one! I’ve already told so many people about my wonderful hotel experience.

Reviewed on Dec 9, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $632, price is now $393 per person
$393
per person
Feb 14 - Feb 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Amazing hotel, location, staff, and food!!

Reviewed on Dec 8, 2025

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 $530, price is now $339 per person
$339
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,229 reviews)
This place was amazing !

Reviewed on Dec 9, 2025

La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $714, price is now $460 per person
$460
per person
Jan 9 - Jan 12
found 16 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
The room was spotless and the staff was good. Loved the hotel. Was just an overnight stay. Wish we had stayed another day. Loved the area.

Reviewed on Nov 30, 2025

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 showing a city

Downtown Chicago

5 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

Little Italy Hotel Deals

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
$92 nightly
The price is $108 total per night from Dec 18 to Dec 19
$108 total
Dec 18 - Dec 19
Total with taxes and fees
8.4/10 Very Good! (5,361 reviews)
Everything was prefect. My only gripe was the heat was not heating as it should on 80 degrees. It was 20 degrees outside everyday. Other than that i will definitely return for another stay.. staff and Valetn were very professional and accommodating...10 star stay...

Reviewed on Dec 10, 2025

Embassy Suites by Hilton Chicago Downtown River North
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
$106 nightly
The price is $124 total per night from Dec 17 to Dec 18
$124 total
Dec 17 - Dec 18
Total with taxes and fees
8.8/10 Excellent! (3,456 reviews)
Clean room and friendly staff. We would definitely visit again.

Reviewed on Dec 10, 2025

Hilton Chicago/Magnificent Mile Suites
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $149 total per night from Jan 4 to Jan 5
$149 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.2/10 Wonderful! (2,109 reviews)
Awesome stay in an amazing room - lobby and bar/restaurant area were excellent as well. Location was perfect for our show at the CIBC Theatre nearby.

Reviewed on Dec 10, 2025

Silversmith Hotel Chicago Downtown
See all 4,799 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Little Italy

University of Illinois Chicago

University of Illinois Chicago

4/5(832 reviews)

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

University of Illinois Chicago

Credit Union 1 Arena

4/5(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.

Credit Union 1 Arena

Jane Addams' Hull-House Museum

You can spend time exploring the galleries in Jane Addams' Hull-House Museum during your travels in Chicago. Discover the fascinating museums and notable monuments in this vibrant area.

Jane Addams' Hull-House Museum

Things to do

River tour boat in Chicago

Architecture River Tour

$54
per adult
96% of travellers recommend
Architecture River Tour
Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$98
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$45
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture 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.