Little Italy Vacations

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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
A busy city street with tall buildings, a bus, and cars.

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

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
The price is NT$4,738 per night from Jul 2 to Jul 3
NT$4,738
NT$5,633 total
Jul 2 - Jul 3
includes taxes & fees
8/10 Very Good! (10,176 reviews)
"In the 1980s and 1990s, I often stayed at this hotel when I went to Chicago for conferences or events at the Art Institute of Chicago. The location is still great for getting to the Art Institute (easy walking distance). Sadly, the hotel has become shabby. The bathroom in my unit appeared to have ..."

Reviewed on 2026/6/30

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$4,868 per night from Jul 6 to Jul 7
NT$4,868
NT$6,849 total
Jul 6 - Jul 7
includes taxes & fees
9.2/10 Wonderful! (1,821 reviews)
"Quiet room, with plenty of space to relax. Great location on the Mag Mile. Breakfast cost was very high and there are other smaller neighborhood breakfast spots to go to. Bar/lounge was great. Did not eat there for dinner but menu looked good."

Reviewed on 2026/6/30

Omni Chicago 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
The price is NT$5,094 per night from Jul 6 to Jul 7
NT$5,094
NT$6,057 total
Jul 6 - Jul 7
includes taxes & fees
9/10 Wonderful! (4,488 reviews)
"The shower was awful. The curtain wouldn’t fully close on either end due to the rod slanting upwards which led to water getting everywhere on the floor. The water pressure was also terrible and"

Reviewed on 2026/6/30

Hilton Chicago/Magnificent Mile Suites
See all 4,484 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 vacation package cost?
From as little as . Yes, you read that correctly. Our Little Italy vacation 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 vacation 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 Center. 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 travelers.
How far in advance should I book my Little Italy vacation?
Travelers 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 vacation is just clicks away.
Can I choose my airline with a Little Italy Expedia vacation package?
With a vacation 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 vacation package?
If your vacation 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.

Stay near popular Little Italy attractions

University of Illinois Chicago

8.4/10 (1,058 reviews)
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.