Little Italy Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$989, price is now S$696 per person
S$696
per person
17 Oct - 20 Oct
found 1 day ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
8.4/10 Very Good! (1,450 reviews)
I think this is a good hotel in an extremely convenient location whether you plan to walk or catch a ride. Close to everything and staff was pleasant.

Reviewed on 19 Aug, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,791, price is now S$1,134 per person
S$1,134
per person
17 Oct - 20 Oct
found 1 day ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$2,043, price is now S$1,388 per person
S$1,388
per person
17 Oct - 20 Oct
found 1 day ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,206, price is now S$848 per person
S$848
per person
17 Oct - 20 Oct
found 1 day ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
Loved the atmosphere and friendly atmosphere

Reviewed on 18 Aug, 2025

L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,382, price is now S$984 per person
S$984
per person
17 Oct - 20 Oct
found 1 day ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.6/10 Exceptional! (2,837 reviews)
Property was well located to be able to explore Chicago easily. Very clean hotel and the staff was extremely accommodating. The only thing missing was a pool but it wasn’t a huge issue. Very nice hotel and would go back for sure.

Reviewed on 20 Aug, 2025

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 which includes a city

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
The price is S$284 per night from 14 Sept to 15 Sept
S$284
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (9,026 reviews)
"Family had a great stay."

Reviewed on 21 Aug, 2025

Congress Plaza Hotel
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
The price is S$228 per night from 1 Sept to 2 Sept
S$228
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,210 reviews)
"The room and view were super nice. Even with not being on the waterfront side of the build we werent disappointed. Check in staff could be nicer but the bar staff was excellent. Nice and informative for travelers. The pier was i. Walking distance. Food and shopping all around and spotless insude ..."

Reviewed on 20 Aug, 2025

The Wade
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
The price is S$230 per night from 4 Sept to 5 Sept
S$230
4 Sept - 5 Sept
includes taxes & fees
8.4/10 Very Good! (4,728 reviews)
"The hotel was wonderfully nestled downtown and an easy walk to sites and restaurants."

Reviewed on 18 Aug, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,697 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 S$696. 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

University of Illinois Chicago

University of Illinois Chicago

Enjoy the student vibe at University of Illinois Chicago during your visit to Chicago. Stroll along the riverfront or experience the acclaimed art galleries in this vibrant area.

University of Illinois Chicago

Things to do

Chicago Hauntings Original Ghost Bus Tour

Chicago Hauntings Original Ghost Bus Tour

S$76
per adult
Chicago Hauntings Original Ghost Bus Tour
Boystown (North Halsted) - Boystown

Tour Chicago LGBTQ Style: On and Off History Bus Tour

S$64
per adult
Tour Chicago LGBTQ Style: On and Off History Bus Tour
River tour boat in Chicago

Architecture River Tour

S$53
per adult
96% 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.