Little Italy Hotels, Chicago

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
8 Dec - 9 Dec
Tomorrow
9 Dec - 10 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Filter by

Guest rating
Guest rating
Star rating

4796 Cheap Hotels in Little Italy - Specials, Reviews, & Last Minute Deals

Garden
Courtyard by Marriott Chicago at Medical District/UIC

Courtyard by Marriott Chicago at Medical District/UIC

3.5 star property
Little Italy
8.8 out of 10, Excellent, (1001)
"Room was clean , staff was great, enjoyed my stay ."
United States
Michael Keith
The price is NZ$162
includes taxes & fees
17 Dec - 18 Dec
Courtyard by Marriott Chicago at Medical District/UIC
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4.0 star property
River North, 3.7 km from Little Italy
9.0 out of 10, Wonderful, (3151)
"Amazing and will be staying again!"
United States
Angie
The price is NZ$190
includes taxes & fees
6 Jan - 7 Jan 2026
Eurostars Magnificent Mile
Terrace/patio
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
Streeterville, 4 km from Little Italy
8.8 out of 10, Excellent, (2182)
"Nice Hotel"
United States
Alan
The price is NZ$182
includes taxes & fees
16 Dec - 17 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
Reception
River Hotel

River Hotel

4.0 star property
The Loop, 3.3 km from Little Italy
8.8 out of 10, Excellent, (4850)
"Location of the Hotel is very nice and the hotel is very clean."
United States
Khaing
The price is NZ$166
includes taxes & fees
21 Dec - 22 Dec
River Hotel
Ballroom
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 star property
Streeterville, 4.5 km from Little Italy
9.0 out of 10, Wonderful, (3447)
"Great place to stay "
United States
RaShawna
The price is NZ$213
includes taxes & fees
14 Dec - 15 Dec
Hilton Chicago/Magnificent Mile Suites
Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3.0 star property
Streeterville, 4 km from Little Italy
8.6 out of 10, Excellent, (2955)
"Great location and great staff!!"
United States
lynne
The price is NZ$171
includes taxes & fees
11 Dec - 12 Dec
Aloft Chicago Mag Mile
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
Streeterville, 5.1 km from Little Italy
9.4 out of 10, Exceptional, (2260)
"Smooth check in and beautiful hotel"
United States
Monique
The price is NZ$253
includes taxes & fees
6 Jan - 7 Jan 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Bar (on property)
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
River North, 3.5 km from Little Italy
8.4 out of 10, Very good, (4232)
"Staff were amazing."
United States
Debra
The price is NZ$167
includes taxes & fees
18 Dec - 19 Dec
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Exterior
Hilton Chicago

Hilton Chicago

4.0 star property
The Loop, 2.6 km from Little Italy
8.4 out of 10, Very good, (2359)
"We had a great stay and will be back again."
United States
Amber
The price is NZ$282
includes taxes & fees
21 Dec - 22 Dec
Hilton Chicago
Property amenity
citizenM Chicago Downtown

citizenM Chicago Downtown

4.0 star property
Theatre District, 3.3 km from Little Italy
9.4 out of 10, Exceptional, (4097)
"I enjoyed my stay with this hotel and would stay here again"
United States
Kim Leticia Terrelle
The price is NZ$217
includes taxes & fees
14 Dec - 15 Dec
citizenM Chicago Downtown
Seasonal outdoor pool, open 8:00 AM to 10:00 PM, pool loungers
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3.0 star property
West Loop, 1.5 km from Little Italy
8.4 out of 10, Very good, (1006)
"Amazing staff clean and secure hotel "
United States
Aniyah
The price is NZ$226
includes taxes & fees
25 Dec - 26 Dec
Holiday Inn & Suites Chicago - Downtown by IHG
Exterior
FOUND Hotel Chicago River North

FOUND Hotel Chicago River North

2.0 star property
River North, 3.3 km from Little Italy
8.4 out of 10, Very good, (364)
"love this place definitely coming back !"
United States
Dayanara
The price is NZ$131
includes taxes & fees
5 Jan - 6 Jan 2026
FOUND Hotel Chicago River North
Cocktail bar
Freehand Chicago

Freehand Chicago

4.0 star property
River North, 3.6 km from Little Italy
8.0 out of 10, Very good, (2628)
"The room was spotless and the staff where great!"
United States
Maria
The price is NZ$143
includes taxes & fees
4 Jan - 5 Jan 2026
Freehand Chicago
Lobby
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4.0 star property
Theatre District, 2.9 km from Little Italy
9.2 out of 10, Wonderful, (2114)
"Would stay again. "
United States
Montroy
Silversmith Hotel Chicago Downtown
Front of property
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4.0 star property
Streeterville, 3.9 km from Little Italy
9.4 out of 10, Exceptional, (2941)
"Great rooms, love the bar and amazing breakfast!"
United States
Michelle
The price is NZ$250
includes taxes & fees
9 Dec - 10 Dec
Hotel Riu Plaza Chicago
Banquet hall
Congress Plaza Hotel

Congress Plaza Hotel

3.5 star property
The Loop, 2.7 km from Little Italy
8.0 out of 10, Very good, (9642)
"Great stay comfortable bed and great location!"
United States
Kimberly Noel
The price is NZ$245
includes taxes & fees
13 Dec - 14 Dec
Congress Plaza Hotel
American cuisine
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 star property
1.6 km from Little Italy
9.0 out of 10, Wonderful, (1748)
"The location was great!!"
United States
Yvette
The price is NZ$174
includes taxes & fees
14 Dec - 15 Dec
Crowne Plaza Chicago West Loop by IHG
Rooftop terrace
Best Western River North Hotel

Best Western River North Hotel

2.5 star property
River North, 3.4 km from Little Italy
7.8 out of 10, Good, (1023)
"Staff was very friendly "
United States
david
The price is NZ$173
includes taxes & fees
4 Jan - 5 Jan 2026
Best Western River North Hotel
Ballroom
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4.0 star property
Theatre District, 2.8 km from Little Italy
8.4 out of 10, Very good, (2122)
"Loved and enjoyed our stay"
United States
Luis
The price is NZ$252
includes taxes & fees
28 Dec - 29 Dec
Palmer House a Hilton Hotel
Exterior
La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown

3.0 star property
The Loop, 2.3 km from Little Italy
8.6 out of 10, Excellent, (2637)
"The hotel was very clean and convenient. I really enjoyed my stay. I would stay there again."
United States
Philip
The price is NZ$225
includes taxes & fees
1 Jan - 2 Jan 2026
La Quinta Inn & Suites by Wyndham Chicago Downtown
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.
View all properties

Our guide on where to stay in Little Italy

Find the best Little Italy areas for the activities you enjoy most.
Downtown Chicago featuring a city

Downtown Chicago

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 - River North

Magnificent Mile

An avenue brimming with superb shops and restaurants, the Magnificent Mile more than lives up to its name.

The Loop - Downtown which includes a river or creek

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.

Chicago showing rides

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).

Top Little Italy Hotel Reviews

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

10/10 Excellent
"Wonderful staff. Very friendly and knowledgeable about local events and recommendations for entertainment. Property was clean at all times and walkable even during inclement weather conditions. I would definitely return."
Jeneen 1-night trip
Posted 19 hours ago
Sable at Navy Pier Chicago, Curio Collection by Hilton

Explore a world of travel with Expedia

Frequently asked questions

What's it like in Little Italy?
Travellers to Chicago's Little Italy neighbourhood will be sure to enjoy a stay here. Are you looking for Little Italy travel tips? Make sure that you visit Credit Union 1 Arena and Jane Addams' Hull-House Museum while you're in the neighbourhood.
Where is the best place to stay in Little Italy?
Based on Expedia customer reviews, Courtyard by Marriott Chicago at Medical District/UIC is the highest ranked property in Little Italy. This hotel offers a restaurant and a fitness centre.
How many hotels are there in the Little Italy area?
Expedia has 29 hotels and other accommodation options in Little Italy to choose from, making this an ideal home base for exploring the greater Chicago area.
If I need to cancel my hotel reservation in Little Italy, will I receive a refund?
Yes, the majority of hotel room reservations are refundable if you cancel before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If your reservation is non-refundable, it may still be possible to cancel it and receive a refund within 24 hours of booking. Enter dates in and click on "Search", then use the "fully refundable" filter to review the best options available in Little Italy.
What are the top things to see and do in Little Italy?
Credit Union 1 Arena, Jane Addams' Hull-House Museum and Provision Theater are just a few attractions to check out in Little Italy. While you're out sightseeing, Michigan Avenue and United Center are a couple of additional sights to visit in Chicago.
How can I get around Little Italy and the greater Chicago area?
Looking for a quick way to explore more of the city? Catch a ride on metro transit at Racine Station and UIC-Halsted Station. To venture out of town, take a train from Chicago Halsted Station.