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
Downtown Chicago
Save 100% on your flight
Price was $744, price is now $472 per person
$472
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,767 reviews)
Overall, the hotel was okay for the price, but pretty basic. The room was very simple and lacked some expected amenities—there were no slippers provided, which was a bit disappointing. Also, the area around the bed wasn’t very clean, which affected the overall experience.
I paid $170 per night, and for that price, I expected a bit more attention to cleanliness and comfort. It’s not terrible, but definitely not great either.
Reviewed on Jun 22, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,231, price is now $772 per person
$772
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was $1,034, price is now $651 per person
$651
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.
Reviewed on Jun 19, 2026
Hampton Inn & Suites Chicago Medical District UIC
Near West Side
Save 100% on your flight
Price was $817, price is now $541 per person
$541
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (622 reviews)
James at the front desk was absolutely incredible. It was a quick stay due to storms in the area, but James' professionalism and care added some positivity to an otherwise stressful travel experience.
Reviewed on Jun 22, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $862, price is now $599 per person
$599
per person
Sep 18 - Sep 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,464 reviews)
The location was great for getting around the city, near bus and train stops which were convenient. The magnificent mile and river were in walking distance. The hotel is very clean and updated. The continental breakfast was the best I’ve seen. Would definitely stay again.
Reviewed on Jun 23, 2026
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
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Little Italy Hotel Deals
Congress Plaza Hotel
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
Hilton Chicago/Magnificent Mile Suites
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
The Chicago Hotel Collection - Magnificent Mile
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
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
University of Illinois Chicago
Enjoy the collegiate vibe at University of Illinois Chicago during your stay in Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area.
Credit Union 1 Arena
Catch an event at Credit Union 1 Arena during your trip to Chicago. Stroll along the riverfront or experience the acclaimed art scene in this vibrant area.
Jane Addams' Hull-House Museum
You can spend time exploring the galleries in Jane Addams' Hull-House Museum during your travels in Chicago. Discover the entertainment choices and notable monuments in this vibrant area.
Things to do
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
$154
per adult
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.