Little Italy Trips (flight + hotel)

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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

5 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 Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Top hotels in Little Italy

River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is P4,720 per night from 5 Mar to 6 Mar
P4,720
P5,541 total
includes taxes & fees
Mar 5 - Mar 6
8.6/10 Excellent! (3,801 reviews)
"Biggest downsides to the property is that you are adjacent to Wacker and Michigan - both have high possibilities for noise (sirens, honking, etc) which I dealt with during my stay. Good dining options in the area, many within a 5 minute walk. Room size was fairly compact, but for a one night stay ..."

Reviewed on Feb 17, 2025

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 P4,956 per night from 18 Feb to 19 Feb
P4,956
P5,818 total
includes taxes & fees
Feb 18 - Feb 19
7.8/10 Good! (8,481 reviews)
"Good spot to the lake shore, but it is very crowded in the elevator."

Reviewed on Feb 15, 2025

Congress Plaza Hotel
L7 Chicago by LOTTE
L7 Chicago by LOTTE
4.5 out of 5
225 N Wabash Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is P7,462 per night from 23 Feb to 24 Feb
P7,462
P8,760 total
includes taxes & fees
Feb 23 - Feb 24
9.6/10 Exceptional! (1,634 reviews)
Fantastic hotel
"This might be the best hotel in the area."

Reviewed on Feb 16, 2025

L7 Chicago by LOTTE
See all 4,307 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.

Popular places to visit

Credit Union 1 Arena

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

Credit Union 1 Arena

Things to do

Chicago Hauntings Original Ghost Bus Tour

Chicago Hauntings Original Ghost Bus Tour

P3,442
per adult
Chicago Hauntings Original Ghost Bus Tour
Flyover in Chicago

Flyover in Chicago

P2,219
per adult
96% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

P3,162
per adult
94% of travellers recommend
Architecture River Tour
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.