Little Italy Travel Guide

Tourist Guide

Chicago skyline panorama with Buckingham Fountain at night, United States
buckingham fountain, chicago ilinois
Little Italy
Tri Taylor
Little Italy

Stay near popular Little Italy attractions


Our pick of the best Little Italy Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is AU$230 per night from 29 June to 30 June
AU$230
29 June - 30 June
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8/10 Very Good! (10,265 reviews)
"The room had been updated, but the halls and some other areas have definitely seen better days. The room was comfortable and the bed was great. You could easily hear the street noise from inside the room with the windows closed. The lobby is still beautifully maintained. Great location with public ..."

Reviewed on 14 June 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The price is AU$244 per night from 30 June to 1 July
AU$244
30 June - 1 July
includes taxes & fees
Stay at this boutique hotel in Chicago. Enjoy free Wi-Fi, 2 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in their ...
7.8/10 Good! (1,580 reviews)
"The hotel was a great location and very clean and and staff was nice and friendly!"

Reviewed on 14 June 2026

The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
The price is AU$246 per night from 5 July to 6 July
AU$246
5 July - 6 July
includes taxes & fees
Stay at this business-friendly hotel in Rosemont. Enjoy free Wi-Fi, breakfast (surcharge) and a free airport shuttle. Our guests praise the helpful staff and ...
8.8/10 Excellent! (2,666 reviews)
"Overall stay was great with my brother. I will come back agin. Staff were helpful especially with our shuttle ride to the airport."

Reviewed on 13 June 2026

Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
The price is AU$264 per night from 29 June to 30 June
AU$264
29 June - 30 June
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, a 24-hour fitness centre and valet parking (surcharge). Our guests praise the helpful staff ...
8.2/10 Very Good! (1,602 reviews)
"This review reflects both the hotel and Expedia’s handling of the booking. The good: The location is excellent and very accessible. The common areas, including the lobby and bar, are pleasant and well maintained. The bad: The hotel is showing its age. The AC struggled to keep the room comfortable ..."

Reviewed on 13 June 2026

The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
The price is AU$460 per night from 5 July to 6 July
AU$460
5 July - 6 July
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge) and a free airport shuttle. Our guests praise the helpful staff and ...
8.4/10 Very Good! (2,342 reviews)
"Welcoming, helpful staff, Clean, quiet room, Lovely, comfortable Hilton bed. Outstanding fitness room with new Life Fitness equipment! Great breakfast and Honors benefits, Just steps to terminal and train service."

Reviewed on 13 June 2026

Hilton Chicago O'Hare Airport
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
The price is AU$256 per night from 5 July to 6 July
AU$256
5 July - 6 July
includes taxes & fees
Stay at this hotel in Chicago. Enjoy free Wi-Fi, room service and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms in their ...
8/10 Very Good! (3,107 reviews)
"It’s convenient location"

Reviewed on 14 June 2026

Freehand Chicago
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.

Our guide on where to stay in Little Italy

Find the best Little Italy areas for the activities you enjoy most.

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

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

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.

Lincoln Park

Known for its ample dining options and fantastic lake views, there's plenty to explore in Lincoln Park. You can visit top attractions like Lake Michigan and Lincoln Hall, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.



Little Italy Travel Guide

Choose two or more items and save on your trip: