Little Italy Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to CA $775 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Little Italy

Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 28 - Jul. 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The hotel is beautiful and everything was so lovely.

Reviewed on May 27, 2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 8 - Aug. 13
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (977 reviews)
The staff has been wonderful, friendly, and accomodating. My 3 year old made best friends with one of the doormen.

Reviewed on May 25, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 28 - Jul. 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,190 reviews)
Beautiful hotel and great staff. The 16th floor Terrace restaurant manager Camila was also the nicest and most professional lady.

Reviewed on May 27, 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 28 - Jul. 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (687 reviews)
This is probably the very best location to stay when visiting Chicago. A beautiful old Art Deco building that has been beautifully maintained. We loved staying here. Easy walk to everything.

Reviewed on May 25, 2024

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 8 - Aug. 13
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
This hotel was very unique and attractive in a convenient location, really liked how easy everything was and straight forward

Reviewed on May 27, 2024

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

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Millennium Park are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotel + flight trips 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 CA $223 per night from May 29 to May 30
CA $223
CA $261 total
includes taxes & fees
May 29 - May 30
7.6/10 Good! (6,802 reviews)
"No parking available"

Reviewed on May 24, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from May 28 to May 29
CA $193
CA $227 total
includes taxes & fees
May 28 - May 29
8.6/10 Excellent! (2,900 reviews)
Perfect for a get away weekend
"Hotel was clean, high end, with friendly and helpful staff. The Valet in particular was a kind Italian gentleman who was helpful and informative. Only issue from my end was the “parking” I paid for turned out to be a lot several blocks from the hotel. I chose just to use the valet service but save ..."

Reviewed on May 25, 2024

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $245 per night from May 29 to May 30
CA $245
CA $288 total
includes taxes & fees
May 29 - May 30
8.2/10 Very Good! (1,953 reviews)
Outstanding Front desk staff and Hotel
"Very Nice Hotel, In the heart of Chicago. Friendly and professional staff and the vallet guys are top notch not to mention cool. You are legit in walking distance of some if not all of what Chicago has to offer in terms of touristy type tings."

Reviewed on May 26, 2024

Eurostars Magnificent Mile
See all 4,186 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Little Italy vacation package cost?
From as little as CA $725. 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(32 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 Credit Union 1 Arena

Credit Union 1 Arena

Catch an event at Credit Union 1 Arena during your trip to Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area.

Credit Union 1 Arena
Image for UIC Forum

UIC Forum

Learn about the events happening at UIC Forum during your trip to Chicago. While you're in the area, find time to visit its shops.

UIC Forum

Things to do

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

CA $255
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago Pizza Tour

Chicago Pizza Tour

CA $121
Per adult
100% of travellers recommend
Chicago Pizza Tour
Image for Chicago: City Minibus Tour with Optional Architecture Cruise

Chicago: City Minibus Tour with Optional Architecture Cruise

CA $64
Per adult
98% of travellers recommend
Chicago: City Minibus Tour with Optional Architecture Cruise
See all activities in Chicago

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.