Little Italy Vacations from $472

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Your Little Italy Vacation

A well-liked food-lovers neighborhood, Little Italy tempts visitors with its cafes, markets and bars and pubs. Lock in a vacation package to Little Italy and look forward to experiencing all of those highlights and more. Kick off your trip to Little Italy by checking out nearby attractions such as University of Illinois Chicago, United Center and Anna and Frederick Douglass Park. Expedia can help you turn your dream Little Italy vacation into reality, whatever your travel plans or budget.

The Latest Little Italy Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Level Chicago – Old Town
Level Chicago - River North
Hampton Inn & Suites Chicago Medical District UIC
Hotel Riu Plaza Chicago

Where to stay in Little Italy

Find the best Little Italy areas and neighborhoods for the activities you enjoy most. Learn more about Little Italy

Little Italy Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $162 total per night from Jun 29 to Jun 30
$162 total
Jun 29 - Jun 30
Total with taxes and fees
8/10 Very Good! (10,167 reviews)
"Room smelled a little like mold or sitting water although the floors were never and the room was clear overall. The shower had a lot of rust in it. Hotel does not offer parking and the garage they recommend is was already full."

Reviewed on Jun 23, 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $166 total per night from Jul 6 to Jul 7
$166 total
Jul 6 - Jul 7
Total with taxes and fees
9/10 Wonderful! (4,465 reviews)
"Great location, rooms and service"

Reviewed on Jun 23, 2026

Hilton Chicago/Magnificent Mile Suites
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $146 total per night from Jun 29 to Jun 30
$146 total
Jun 29 - Jun 30
Total with taxes and fees
7.8/10 Good! (1,615 reviews)
"Stunning room, lobby, and spectacular views from the rooftop lounge. That being said, room service could’ve been more attentive. We asked for body wash for our room, as it was out when we checked in. Even after calling the front desk, this small request went unanswered. Barring that, it was a good ..."

Reviewed on Jun 23, 2026

The Chicago Hotel Collection - Magnificent Mile
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.

Discover the most popular places to visit in Little Italy

Things to do

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.