Little Italy Holidays from £1,014

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Your University Village / Little Italy Holiday

Cafes, markets and bars and pubs are just a few of the things to look forward to when you lock in a holiday package to University Village / Little Italy. Whether you're seeking relaxation, adventure or something else, this food-lovers neighbourhood has it all. Eager to sightsee during your trip to University Village / Little Italy? Don't miss nearby attractions such as Millennium Park, Willis Tower and Art Institute of Chicago. Don't just dream it — turn it into a reality! Secure your perfect University Village / Little Italy holiday with Expedia and enjoy travelling your way.

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,554, price is now £1,014 per person
£1,014
per person
27 Oct - 31 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.

Reviewed on 25 Aug 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was £2,303, price is now £1,465 per person
£1,465
per person
8 Oct - 15 Oct
found 21 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (2,087 reviews)
Loved the view from the room of Lake Michigan.

Reviewed on 25 Aug 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was £2,172, price is now £1,399 per person
£1,399
per person
8 Oct - 15 Oct
found 21 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9/10 Wonderful! (1,962 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.

Reviewed on 25 Aug 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £2,020, price is now £1,307 per person
£1,307
per person
8 Oct - 15 Oct
found 21 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
8.2/10 Very Good! (2,061 reviews)
Great property. Clean and convenient. Only unsightly thing is that there was a dirty t shirt laying in the hallway that nobody seemed to pick up.

Reviewed on 26 Aug 2025

Holiday Inn Express Chicago - Magnificent Mile by IHG

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 out of 5
Downtown Chicago
Price was £1,907, price is now £1,267 per person
£1,267
per person
8 Oct - 15 Oct
found 21 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
8.4/10 Very Good! (1,011 reviews)
Bed was comfortable, breakfast good, room VERY small

Reviewed on 24 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 featuring 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

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £132 per night from 1 Sept to 2 Sept
£132
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,219 reviews)
"Friendly"

Reviewed on 24 Aug 2025

The Wade
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 £117 per night from 1 Sept to 2 Sept
£117
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (8,995 reviews)
"Transportation by bus or subway is within a 5 minute walk, very easy. Hotel is across from a beautiful park. Lobby is nice but the hallways look very rough. It’s an old hotel with basic upgrades. Rooms were clean but shows it age. Beds were comfy. We checked our luggage upon arrival because our room ..."

Reviewed on 23 Aug 2025

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 £133 per night from 3 Sept to 4 Sept
£133
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,752 reviews)
"Great location. Nice size rooms. Breakfast was really good, only way to busy and crowded during that experience. They should extend the breakfast hours by an hour to reduce the over crowding. Overall good stay. Would return.."

Reviewed on 23 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does an University Village / Little Italy travel package cost?
Customize your University Village / Little Italy travel package from a low £1,014. Pick from any combination of rental cars, flights and hotels to craft the getaway of your dreams. Don't forget to add on a few experiences or tours!
If I'm not able to travel, can I cancel my University Village / Little Italy travel package?
Yes, you can. We totally understand that life doesn't always go to plan, so we're happy to help if you have to make changes to your University Village / Little Italy travel package. It may be possible to cancel or amend your itinerary for free if you've booked within 24 hours. Your airline, hotel or car rental company may impose a fee if you booked more than 24 hours ago. Have a look at our Customer Service Portal for more information. Also, be sure to check your itinerary for the nitty-gritty on change fees.
How do I get a cheap travel package to University Village / Little Italy?
Just imagine all the thrilling things you could do in University Village / Little Italy with a wad of extra cash in your pocket. Watch your savings stack up when you bundle your airfare and hotel bookings into an University Village / Little Italy travel package. You have loads of choice when you book with Expedia too. In fact, you can select from over 550 airlines and 1,000,000 hotel options globally. Whether you're heading off with the entire family or embarking on a solo adventure, planning a getaway to University Village / Little Italy is better with a package.
Does Expedia offer Book Now, Pay Later University Village / Little Italy holidays?
Your bank balance shouldn't stop you from escaping on holiday, so Expedia has devised a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book a terrific getaway without drying up your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your trip. Check out these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month works for you, Klarna can help. Paying in convenient monthly instalments will make that dream getaway possible.
  • Pay in instalments holidays: If you'd like to pay off your escape across multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: When you spot an unbeatable deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you lock in your escape.

Where should I stay in University Village / Little Italy?
Most people who visit University Village / Little Italy include Millennium Park and Wrigley Field on their must-see lists. Why not go for a hotel near these main attractions?
What are the top hotels in University Village / Little Italy?
Hyatt Regency Chicago and The Godfrey Hotel Chicago are a couple of the most well-known hotels in University Village / Little Italy. Why not check out the amenities and facilities at each and then make up your mind?
How far in advance should I book my University Village / Little Italy holiday?
While prices fluctuate, we generally suggest booking your seats as early as possible. Most international airfares become available on Expedia up to 12 months in advance. If circumstances have left you booking late, you may still get lucky. Cheap journeys to University Village / Little Italy sometimes appear only weeks before departure.
What does an Expedia University Village / Little Italy travel package include?
Choose from any combination of flights, hotels and rental cars. Once you've made your booking, you can add the fun stuff like tours and experiences. Want to pick your airfare class? That's easily done too. The choice is yours when it comes to putting together your perfect University Village / Little Italy trip.
What should I know before booking an University Village / Little Italy travel package?
Bundling your bookings into an University Village / Little Italy travel package is the most convenient way to organise your trip. Not only that, you'll get great discounts just for combining your hotels, flights and car rentals. Once you've booked, why not add on a tour or an activity?
Can I choose my airline with an University Village / Little Italy Expedia travel package?
Yes, and with more than 550 airlines to pick from across the globe, you have plenty of choice. Look through the available options and see which airline suits your budget and needs.

Things to do

Chicago Hauntings Original Ghost Bus Tour

Chicago Hauntings Original Ghost Bus Tour

£43
per adult
Chicago Hauntings Original Ghost Bus Tour
River tour boat in Chicago

Architecture River Tour

£31
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
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. Flight-inclusive packages are ATOL protected.