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
Downtown Chicago showing a city

Downtown Chicago

4 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 hotel + flight trips in Downtown Chicago

Little Italy Hotel Deals

River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NT$5,255 per night from Jul 2 to Jul 3
NT$5,255
per night
Jul 2 - Jul 3
8.6/10 Excellent! (2,952 reviews)
"This was such a conveniently located hotel. We were able to walk to so many places. The guy that checked us in was super friendly and set the tone for a really nice stay. I also really appreciated to cold filtered water stations all over to refill our water bottles. I would definitely stay here ..."

Reviewed on 2024/6/16

River Hotel
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$5,334 per night from Jun 18 to Jun 19
NT$5,334
per night
Jun 18 - Jun 19
7.6/10 Good! (6,990 reviews)
"I love the area the Hotel is in. Almost Everything you need to see in Chicago is in walking distance."

Reviewed on 2024/6/16

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NT$6,169 per night from Jul 2 to Jul 3
NT$6,169
per night
Jul 2 - Jul 3
8/10 Very Good! (2,395 reviews)
"Alma was our checkin agent and she was amazing! So kind!! Do miss the extra sink in bedroom and would love another chair for seating Otherwise great"

Reviewed on 2024/6/16

Embassy Suites by Hilton Chicago Downtown River North
See all 4,194 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.

Discover the most popular places to visit in Little Italy

Image for University of Illinois Chicago

University of Illinois Chicago

4/5(832 reviews)

Enjoy the collegiate vibe at University of Illinois Chicago during your stay in Chicago. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.

University of Illinois Chicago
Image for Wrigley Field

Wrigley Field

4.5/5(2,128 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Image for Six Flags Great America

Six Flags Great America

4.5/5(347 reviews)

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

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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.