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19 Dec - 20 Dec
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20 Dec - 21 Dec
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19 Dec - 21 Dec
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26 Dec - 28 Dec

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Our top choices for Little Italy hotels

Suite, 1 Bedroom | Egyptian cotton sheets, premium bedding, pillow-top beds, in-room safe
Courtyard by Marriott Chicago at Medical District/UIC

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, (1002)
"Room was clean , staff was great, enjoyed my stay ."
United States
Michael Keith
The price is 2.100.655 ₫
2.465.960 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Courtyard by Marriott Chicago at Medical District/UIC
Cocktail bar
Freehand Chicago

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 3.6 km from Little Italy
8.0 out of 10, Very good, (2651)
"It's an excellent place."
United States
Jose
The price is 1.539.954 ₫
2.271.279 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Freehand Chicago
Lobby
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 4 km from Little Italy
8.6 out of 10, Excellent, (2962)
"The room was very clean, the location was excellent."
United States
Craig
The price is 2.079.596 ₫
2.441.237 ₫ total
includes taxes & fees
14 Jan - 15 Jan 2026
Aloft Chicago Mag Mile
Lobby
River Hotel

River Hotel

River Hotel
4.0 star property
The Loop, 3.3 km from Little Italy
8.8 out of 10, Excellent, (4847)
"Great location, comfortable room, and nice staff."
United States
Claudia
The price is 2.189.104 ₫
2.569.789 ₫ total
includes taxes & fees
21 Dec - 22 Dec
River Hotel
Lobby
Congress Plaza Hotel

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, (9668)
"Wonderful stay!"
United States
Zach
The price is 5.663.798 ₫
6.648.732 ₫ total
includes taxes & fees
31 Dec - 1 Jan 2026
Congress Plaza Hotel
Exterior
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Streeterville, 4 km from Little Italy
8.4 out of 10, Very good, (2746)
"Excellent place to stay "
United States
Teniesha
The price is 2.177.521 ₫
3.328.801 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Bar (on property)
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Streeterville, 4.3 km from Little Italy
8.2 out of 10, Very good, (3795)
"Clean room, good location, friendly staff"
United States
Zacharias
The price is 2.015.065 ₫
2.365.486 ₫ total
includes taxes & fees
21 Dec - 22 Dec
The Whitehall Hotel, BW Premier Collection
Exterior
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Streeterville, 4 km from Little Italy
9.0 out of 10, Wonderful, (1054)
"Perfect location to surrounding area and activities, friendly staff, clean rooms, amazing gym, and delicious food."
United States
Hannah
The price is 2.579.752 ₫
3.800.979 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
Hyatt Centric Chicago Magnificent Mile
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton

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, (2269)
"Great staff and restaurants!!"
United States
Abigale
The price is 2.396.010 ₫
3.709.010 ₫ total
includes taxes & fees
15 Jan - 16 Jan 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Exterior
Warwick Allerton - Chicago

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Magnificent Mile, 4 km from Little Italy
8.4 out of 10, Very good, (3008)
"Enjoyed this hotel stay. "
United States
Kimberly
The price is 1.790.032 ₫
2.874.054 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Warwick Allerton - Chicago
Indoor pool
Hilton Garden Inn Chicago Downtown/Magnificent Mile

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, (4263)
"Excellent location Restaurant attached "
United States
Rebecca
The price is 2.266.496 ₫
2.660.640 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Reception
Palmer House a Hilton Hotel

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, (2146)
"Beautiful hotel! Perfect for a holiday staycation! "
United States
Melissa
The price is 3.345.780 ₫
4.585.712 ₫ total
includes taxes & fees
26 Dec - 27 Dec
Palmer House a Hilton Hotel
Terrace/patio
DoubleTree by Hilton Chicago - Magnificent Mile

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, (2196)
"Very friendly staff, clean rooms, the location is amazing and near of everything "
United States
Sarwat
The price is 2.352.839 ₫
2.761.996 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
DoubleTree by Hilton Chicago - Magnificent Mile
Lobby sitting area
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
The Loop, 3.3 km from Little Italy
8.8 out of 10, Excellent, (1991)
"A good place for stay "
United States
Julio
The price is 2.189.104 ₫
2.569.789 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Club Quarters Hotel Wacker at Michigan, Chicago
Exterior
Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
Gold Coast, 4.7 km from Little Italy
9.0 out of 10, Wonderful, (1486)
"Nice stay"
United States
Michelle
The price is 1.705.269 ₫
2.774.423 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Claridge House Chicago, Tapestry Collection by Hilton
City view
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago
4.0 star property
Streeterville, 4.5 km from Little Italy
8.6 out of 10, Excellent, (2007)
"Great location, clean hotel"
United States
Andre
The price is 2.316.512 ₫
3.337.440 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
Millennium Knickerbocker Chicago
Property amenity
Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District
4.0 star property
Theatre District, 2.9 km from Little Italy
8.8 out of 10, Excellent, (1461)
"The staff was super friendly at check-in and the bartender was very nice!"
United States
Jennifer
The price is 2.295.453 ₫
2.694.633 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Cambria Hotel Chicago Loop - Theatre District
2 bars/lounges
Hyatt Regency Chicago

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 3.6 km from Little Italy
9.4 out of 10, Exceptional, (3402)
"The Hotel was amazing great location "
United States
Donnisha
The price is 3.659.036 ₫
5.067.951 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Hyatt Regency Chicago
Pool
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
The Loop, 2.5 km from Little Italy
8.8 out of 10, Excellent, (1761)
"Great check in and responsive front desk staff. Housekeeping staff did a great job during our visit! "
United States
Steven
The price is 1.921.126 ₫
2.255.210 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Hilton Garden Inn Chicago Downtown South Loop
2 restaurants, breakfast, lunch, dinner served; American cuisine
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
The Loop, 3.4 km from Little Italy
9.4 out of 10, Exceptional, (3443)
"Great hotel! "
United States
Kianna
The price is 3.432.123 ₫
4.028.969 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
LondonHouse Chicago, Curio Collection by Hilton
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.
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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

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 - River North

Magnificent Mile

Are you interested in fascinating museums, panoramic lake views and popular shops? A visit to Magnificent Mile might be the perfect thing. You can also explore top sights like Michigan Avenue and Chicago Water Tower.

The Loop - Downtown featuring a river or creek

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.

Chicago which includes 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

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.
How many hotels are there in the Little Italy area?
Expedia has 30 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.