Little Italy Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
Grand Royal Hotel O'Hare - Chicago

Grand Royal Hotel O'Hare - Chicago

3.5 out of 5
Price was S$907, price is now S$691 per person
S$691
per person
28 Mar - 4 Apr
found 5 hours ago
Return direct flight included
Syracuse (SYR) to Chicago (ORD)
5.8/10 (215 reviews)
Friendly front desk, easy and convenient for my overnight layover in Chicago

Reviewed on 7 Nov, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Save 100% on your flight
Price was S$2,021, price is now S$1,404 per person
S$1,404
per person
28 Mar - 4 Apr
found 5 hours ago
Return direct flight included
Syracuse (SYR) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Great stay fir early flights

Reviewed on 8 Jan, 2026

Hilton Rosemont Chicago O'Hare

Hilton Rosemont Chicago O'Hare

3.5 out of 5
Price was S$1,516, price is now S$1,165 per person
S$1,165
per person
28 Mar - 4 Apr
found 5 hours ago
Return direct flight included
Syracuse (SYR) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
The room and staff were extremely friendly, but I specifically requested a room with a bath so I could soak my leg after a surgery. There was absolutely no water pressure when it came to the bath and the drain wouldn't close all the way. For how much I paid I feel like I should have been able to take a bath

Reviewed on 8 Dec, 2025

DoubleTree by Hilton Chicago - Oak Brook

DoubleTree by Hilton Chicago - Oak Brook

4 out of 5
Price was S$1,245, price is now S$957 per person
S$957
per person
28 Mar - 4 Apr
found 5 hours ago
Return direct flight included
Syracuse (SYR) to Chicago (ORD)
6.8/10 (1,000 reviews)
Hotel is old and showing its age. Rooms are old too. Few amenities etc.

Reviewed on 6 Jan, 2026

Motel Edgebrook Chicago North Shore by OYO

Motel Edgebrook Chicago North Shore by OYO

2 out of 5
Forest Glen
Price was S$984, price is now S$757 per person
S$757
per person
28 Mar - 4 Apr
found 5 hours ago
Return direct flight included
Syracuse (SYR) to Chicago (ORD)
6.2/10 (365 reviews)
dated, lamp shade missing, overall dumpy place

Reviewed on 19 Dec, 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

Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$247 per night from 26 Jan to 27 Jan
S$247
26 Jan - 27 Jan
includes taxes & fees
8.4/10 Very Good! (2,501 reviews)
Everything was amazing abt my stay

Reviewed on 7 Jan, 2026

Hilton Chicago
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$247 per night from 26 Jan to 27 Jan
S$247
26 Jan - 27 Jan
includes taxes & fees
8.4/10 Very Good! (2,215 reviews)
Room was clean bathroom was dated. Also pubic hair from the last guest on the bathroom floor which was not great after the 1 hour check in process. Not to mention the additional charges added to my bill.

Reviewed on 4 Jan, 2026

Palmer House a Hilton 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 S$135 per night from 25 Jan to 26 Jan
S$135
25 Jan - 26 Jan
includes taxes & fees
8.8/10 Excellent! (3,678 reviews)
Room and hotel overall very clean. Noted some things that could be updated in bathroom(stopper in sink didnt go all the way down, peeling caulk and some missing grout). Minor updates. Our sink was clogged when we checked in and I called the front desk, housekeeping and the hotel hotline 4 different ...

Reviewed on 7 Jan, 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,814 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$691. 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 entertainment choices in this vibrant area.

University of Illinois Chicago

Things to do

Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

S$57
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

S$32
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

S$51
per adult
92% of travellers recommend
Art Institute of Chicago
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.