Find luxury hotels in Little Italy, Chicago

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Check availability on Little Italy Luxury Hotels

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

Top Little Italy Luxury Hotels

Front of property
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2941)
"Great rooms, love the bar and amazing breakfast!"
United States
Michelle
$123 nightly
The price is $144
Dec 9 - Dec 10
Total with taxes and fees
Hotel Riu Plaza Chicago
Cocktail bar
Freehand Chicago

Freehand Chicago

4.0 star property
Downtown Chicago
8.0 out of 10, Very Good, (2629)
"The room was spotless and the staff where great!"
United States
Maria
$74 nightly
The price is $87
Jan 4 - Jan 5, 2026
Total with taxes and fees
Freehand Chicago
Lobby
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2115)
"Would stay again. "
United States
Montroy
$127 nightly
The price is $149
Jan 4 - Jan 5, 2026
Total with taxes and fees
Silversmith Hotel Chicago Downtown
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3152)
"Amazing and will be staying again!"
United States
Angie
$94 nightly
The price is $110
Jan 7 - Jan 8, 2026
Total with taxes and fees
Eurostars Magnificent 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
Downtown Chicago
9.4 out of 10, Exceptional, (2260)
"Smooth check in and beautiful hotel"
United States
Monique
$125 nightly
The price is $146
Jan 6 - Jan 7, 2026
Total with taxes and fees
Sable at Navy Pier Chicago, Curio Collection by Hilton
American cuisine, alfresco dining
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1915)
"Awesome staff and great location "
United States
Luis C
$115 nightly
The price is $135
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Godfrey Hotel Chicago
Snack bar
Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District

4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1455)
"Clean, modern, friendly/helpful staff, the perfect spot for staying for a show at The Chicago Theatre. Parking was close and easy too. "
United States
Megan
$90 nightly
The price is $106
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cambria Hotel Chicago Loop - Theatre District
Exterior
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1047)
"Great Hotel!"
United States
Wendy
$123 nightly
The price is $144
Jan 1 - Jan 2, 2026
Total with taxes and fees
Hyatt Centric Chicago Magnificent Mile
Reception
Swissotel - Chicago

Swissotel - Chicago

4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3000)
"Very beautiful place to stay"
United States
FaithBrenda
$139 nightly
The price is $163
Jan 2 - Jan 3, 2026
Total with taxes and fees
Swissotel - Chicago
Lobby
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1007)
"Great location and restaurant "
United Kingdom
Asvin
$164 nightly
The price is $192
Jan 2 - Jan 3, 2026
Total with taxes and fees
theWit Chicago, a Hilton Hotel
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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Top Little Italy Hotel Reviews

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent
"Very nice hotel stay. Would definitely go back "
Rahul 6-night trip
Posted 12 hours ago
The Whitehall Hotel, BW Premier Collection

Frequently asked questions

Are you looking for a luxury hotel for your Little Italy vacation?
Let Expedia help you arrange your flight to Chicago Midway Airport (MDW) airport or Chicago O'Hare Intl. Airport (ORD) airport, and then choose from some places to stay that will deliver the luxury you seek. Amenities are an important consideration when you plan a vacation, so we make it easy to get what you need to make your stay special. If you want a posh hotel that has fine dining, a spa, or several swimming pools, Expedia can help you find the best luxury hotel experience that Little Italy offers. Little Italy has some interesting things to see and do including Credit Union 1 Arena and Jane Addams' Hull-House Museum, so you might want to take in the local sights during your visit.
What's there to see and do in Little Italy?
Enjoy Little Italy and visit Credit Union 1 Arena, Jane Addams' Hull-House Museum, and Provision Theater. If you have extra time while you're in the area, you might want to see Michigan Avenue and Wrigley Field.
How can I get around Little Italy?
It's easier to get around town comfortably when you know your options. Local metro stations include Racine Station and UIC-Halsted Station.

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