Little Italy Holidays

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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

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.

Find hotels in Downtown Chicago

Top hotels in Little Italy

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is Rp2.494.399 per night from 29 Jun to 30 Jun
Rp2.494.399
Rp2.965.591 total
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (10,139 reviews)
"Room could’ve been cleaner specifically the floor, conditioner was out. The property is old."

Reviewed on 31 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is Rp3.379.650 per night from 30 Jun to 1 Jul
Rp3.379.650
Rp4.527.675 total
30 Jun - 1 Jul
includes taxes & fees
9.4/10 Exceptional! (4,306 reviews)
"This hotel is absolutely lovely! Immaculate in every area, with very helpful and friendly staff. The room was perfectly appointed. The bathroom door doubled as a door to the toilet and I want one of those in my house! The rain shower with a wand had great water pressure and temperature. I'm not a ..."

Reviewed on 31 May 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is Rp2.717.876 per night from 28 Jun to 29 Jun
Rp2.717.876
Rp3.231.283 total
28 Jun - 29 Jun
includes taxes & fees
7.8/10 Good! (1,496 reviews)
"Everything was great"

Reviewed on 31 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,695 properties in Little Italy
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

How much does a Little Italy holiday package cost?
From as little as . Yes, you read that correctly. Our Little Italy holiday packages are a simple way to make your budget go further. Bundle your preferred hotels, flights and rental car and get out and explore this top destination.
How do I get a cheap travel package to Little Italy?
Creating your own Little Italy holiday package with Expedia is one of the easiest ways to save. We have access to more than 550 partner airlines and 1,000,000 properties across the globe. With such a fabulous range to select from, you'll have no trouble putting together your perfect adventure.
Where should I stay in Little Italy?
A journey to Little Italy isn't complete without stopping by University of Illinois Chicago and United Centre. Reserve a room within walking distance and easily access these famous sights.
What are the top hotels in Little Italy?
Whether you're staying for one night or a week in Little Italy, you'll get a good night's rest at Courtyard by Marriott Chicago at Medical District/UIC. This option is popular with plenty of travellers.
How far in advance should I book my Little Italy holiday?
Travellers are normally able to compare international airfares on Expedia within 12 months of departure. Booking late? With a little bit of luck, it's still possible to score a cheap ticket only weeks before your flight.
What does an Expedia Little Italy travel package include?
Packages include rental cars, hotels and flights, but you can mix and match them to create your dream Little Italy escape. You can also add on some activities and tours once you've made your booking. You're in control! When you combine your bookings with Expedia, you'll enjoy deals you won't find anywhere else.
What should I know before booking a Little Italy travel package?
Design deals that match your budget with an Expedia package. Hotels, airfares, rental cars — we have everything you need to plan your escape. You'll save precious cash just by bundling your bookings. Whether you're going on a snow and ski adventure or venturing someplace warm, your ideal holiday is just clicks away.
Can I choose my airline with a Little Italy Expedia holiday package?
With a holiday package, you're always in charge. Whether you're looking to fly to Little Italy in business or coach, simply choose from the available airline options. Expedia has access to more than 550 airline partners all over the world.
If I'm not able to travel, can I cancel my Little Italy holiday package?
If your holiday plans in Little Italy have been upended, it's a relief to know that it is possible to amend or cancel your booking. If you booked in the last 24 hours, you may be able to get a refund. If your booking is older than that, your airline, hotel or car rental company may charge fees. For more information, check our Customer Service Portal.

Popular places to visit

Addams/Medill Park

After visiting Addams/Medill Park, make a plan to see the other sights and activities in Chicago. Experience the entertainment choices and acclaimed art galleries in this vibrant area.

Addams/Medill Park

Jane Addams' Hull-House Museum

You can spend time studying the exhibits at Jane Addams' Hull-House Museum in Chicago. Discover the fascinating museums and notable monuments in this vibrant area.

Jane Addams' Hull-House Museum

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Rp479.088
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

Rp733.892
per adult
94% of travellers recommend
Skydeck - Willis Tower Admission
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

Rp1.934.096
per adult
88% of travellers recommend
Chicago C3® by CityPASS®
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.