
Little Italy Holidays
- Plan, book, travel with confidence
Better together
Save up to €185 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
per person
6 Nov - 10 Nov
found 23 hours ago
Return flight included
Philadelphia (PHL) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
Overall the staff were very prompt and helpful. My only complaints with the hotel is the rooms are smaller than I expected, the 4 of us had a hard time fitting into a double bed room. It would have been nice to know that most of the food places around the hotel close on the weekend. Definitely not the best choice for a family. Proximity to activities were doable , but a little far. Wells street at night was a little scary over the weekend. Parking in Chicago is really crazy but I found parking for $18 a night on the same block without in and out access. We parked and left the car the whole time. Overall staff was amazing, nothing bad to say there, but I was disappointed as a first time visitor with the size of the hotel rooms, the cleanliness was fair, dark room, windows you couldn’t see out of well. The room temp was set at 65 but we were all swearing overnight and had to purchase a fan to help.
Reviewed on 13 Aug 2025

The Royal Sonesta Chicago River North
Downtown Chicago
Save 100% on your flight
per person
6 Nov - 10 Nov
found 23 hours ago
Return flight included
Philadelphia (PHL) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
so I gotta say The royal sonesta river north in particular is amazing it feels more like a hotel, it feels like a small community and all the staff and guest know each other. The front desk woman Gabby is amazing and dope as heck. Shaunda is a travel guide there, shes hilarious and gave us wonderful recommendations in the area. Antwonne is a dope Bellman great service and attitude. Every detail was perfect Jessenia apart of the housekeeping staff has such good attention to detail when it came to fixing up and cleaning the room everything was so organized and neat. Now to the room it couldn't have been more perfect they upgraded us to the luxury suite and it was beautiful (use the tub as much as you can)
Reviewed on 15 Aug 2025



Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
per person
6 Nov - 10 Nov
found 23 hours ago
Return flight included
Philadelphia (PHL) to Chicago (ORD)
9.2/10 Wonderful! (277 reviews)
Ran into some confusion with my credit card. It was used at check in and then they said they didn’t have it
Reviewed on 9 Aug 2025
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.
Top hotels in Little Italy

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €189 per night from 14 Sept to 15 Sept
€189
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (8,978 reviews)
"Great location. Hotel seems a bit dated"
Reviewed on 13 Aug 2025

Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €161 per night from 3 Sept to 4 Sept
€161
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,709 reviews)
"Nice property. It’s within walking distance to a lot of bars, restaurants and Bally’s casino. It’s right next door to a grocery store which was super convenient. There were a couple of women who worked at the front desk that were unpleasant, and they only have 1 washer/dryer on site, which is hard ..."
Reviewed on 16 Aug 2025

Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €195 per night from 2 Sept to 3 Sept
€195
2 Sept - 3 Sept
includes taxes & fees
8.4/10 Very Good! (1,854 reviews)
"Loved the Palmer House Hotel!!! The lobby, amazing decoration! I even took a picture of it to post on social. The bar and restaurant area, very popular and looked like everyone was enjoying themselves! The room, well, not the best, but this was an occasion where I booked last minute and through a ..."
Reviewed on 15 Aug 2025
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.
Frequently asked questions
Popular places to visit

University of Illinois Chicago
Enjoy the student vibe at University of Illinois Chicago during your visit to Chicago. Stroll along the riverfront or experience the acclaimed art galleries 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 fascinating museums in this vibrant area.
Things to do

Chicago By Night River & Lake Cruise
€39
per adult
96% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.