Little Italy
Chicago
Visit Little Italy
Stay near popular Little Italy attractions
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
88% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
Chicago By Night River and Lake Cruise
CA $69
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $56
per adult
94% of travellers recommend
Little Italy Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
The price is CA $194 per night from Jun 30 to Jul 1
CA $194
CA $230 total
Jun 30 - Jul 1
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! (10,161 reviews)
"Friendly staff. Encountered a cockroach in the elevator."
Reviewed on Jun 29, 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
The price is CA $217 per night from Jul 5 to Jul 6
CA $217
CA $305 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! (1,832 reviews)
"Best location on Michigan Avenue"
Reviewed on Jun 27, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
The price is CA $198 per night from Jul 6 to Jul 7
CA $198
CA $235 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! (4,478 reviews)
"Soooo I paid for the lake view the lake view was not really a lake view the lake is in front of some other buildings I had to have a room change for that reason I appreciated the effort but it was really no difference the carpet in the room looks like it needs to not be there they could do without ..."
Reviewed on Jun 29, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
The price is CA $192 per night from Jul 20 to Jul 21
CA $192
CA $219 total
Jul 20 - Jul 21
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! (2,748 reviews)
"Awesome place to stay and wine and dine"
Reviewed on Jun 28, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
The price is CA $363 per night from Jul 4 to Jul 5
CA $363
CA $427 total
Jul 4 - Jul 5
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! (2,326 reviews)
"Very close to airport"
Reviewed on Jun 29, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
The price is CA $241 per night from Jul 6 to Jul 7
CA $241
CA $327 total
Jul 6 - Jul 7
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! (4,569 reviews)
"I love how everyone can’t go to just any floor with their keycard. That’s great for safety. The rooftop bar was nice and beautiful especially at night. The hotel staff was quick, efficient, and very helpful. Breakfast was amazing and fresh every morning."
Reviewed on Jun 29, 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.
Where to stay in Little Italy
Find the best Little Italy areas and neighborhoods for the activities you enjoy most.
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.
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.
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.
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
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.
