Little Italy, IL

Chicago

A city skyline with illuminated skyscrapers and a vibrant fountain display.
A city skyline with a prominent red building, a large fountain with water jets, and a green sculpture in the foreground.
A bronze statue of a baseball player in a batting pose, with a plaque reading "Joseph Paul DiMaggio The Yankee Clipper".
A cityscape with a prominent skyscraper, a circular building, and a large rectangular building.
A traditional Japanese building by a calm pond with rocks and lush greenery.

Stay near popular Little Italy attractions

University of Illinois Chicago

8.4/5 (1,058 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.
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥3,887
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,853
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

￥6,398
per adult
92% of travellers recommend
Art Institute of Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥6,478
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

￥24,703
per adult
80% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

￥7,838
per adult
90% of travellers recommend
Chicago Crime and Mob Bus Tour
See all activities in Chicago

Little Italy Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is ￥24,054 per night from Jul 2 to Jul 3
￥24,054
￥28,598 total
Jul 2 - Jul 3
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (10,171 reviews)
"Great place to stay in the city"

Reviewed on Jun 30, 2026

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
The price is ￥24,744 per night from Jul 5 to Jul 6
￥24,744
￥34,810 total
Jul 5 - Jul 6
includes taxes & fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,833 reviews)
"Staff was extremely friendly and helpful! Very clean and inviting environment!"

Reviewed on Jun 29, 2026

Omni Chicago Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
The price is ￥25,891 per night from Jul 6 to Jul 7
￥25,891
￥30,785 total
Jul 6 - Jul 7
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
9/10 Wonderful! (4,483 reviews)
"I booked three rooms at this hotel for a speacial occasion trip to celebrate a graduation. At check in I asked if one of the rooms could possibly have some kind of view of the city. I was quickly told it was not possible as the hotel was sold out. I was very sorry that out of the 100's of rooms in ..."

Reviewed on Jun 30, 2026

Hilton Chicago/Magnificent Mile Suites
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
The price is ￥25,747 per night from Jul 2 to Jul 3
￥25,747
￥29,346 total
Jul 2 - Jul 3
includes taxes & fees
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,752 reviews)
"Location close to airport"

Reviewed on Jun 29, 2026

Hyatt Regency O'Hare Chicago
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
The price is ￥40,159 per night from Jul 3 to Jul 4
￥40,159
￥47,143 total
Jul 3 - Jul 4
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very Good! (2,328 reviews)
"Very close to airport"

Reviewed on Jun 29, 2026

Hilton Chicago O'Hare Airport
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is ￥25,863 per night from Jul 5 to Jul 6
￥25,863
￥35,367 total
Jul 5 - Jul 6
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
9.4/10 Exceptional! (4,580 reviews)
"Wonderful hotel in the midst of the action. Resort like buffet breakfast with helpful staff. Great experience"

Reviewed on Jun 29, 2026

Hotel Riu Plaza Chicago
See all 4,484 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.

Where to stay in Little Italy

Find the best Little Italy areas and neighborhoods for the activities you enjoy most.
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

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.

A historic castle-like building with intricate stonework and a paved walkway.

Magnificent Mile

Michigan Avenue and Chicago Water Tower are just a few worthwhile attractions to visit in Magnificent Mile. Travelers also love the fascinating museums, panoramic lake views, and popular shops.

A river with yellow boats, a bridge, and tall buildings.

The Loop

Michigan Avenue and Lake Michigan are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops, and acclaimed art galleries.

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

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.

A river with a city skyline in the background, surrounded by green trees and grass.

Lincoln Park

Known for its ample dining options and fantastic lake views, there's plenty to explore in Lincoln Park. You can visit top attractions like Lake Michigan and Oz Park, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.

Little Italy, IL