Little Italy Holidays from £1,077

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,537, price is now £1,077 per person
£1,077
per person
11 May - 18 May
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.2/10 Very Good! (2,604 reviews)
This was a great price for a great stay!! Central to many locations downtown! I am planning to book this hotel again in the future!

Reviewed on 9 Apr 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,898, price is now £1,243 per person
£1,243
per person
11 May - 18 May
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Great service, loved this place.

Reviewed on 9 Apr 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was £1,789, price is now £1,226 per person
£1,226
per person
17 Jun - 21 Jun
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
Breakfast was very good. Enjoyed our room and how everything was clean. There was no microwave so don’t try to bring food if you need to reheat it. Fridge was also not strong to freeze my ice cream so be aware. All the staff were kind and helpful. Rooftop was beautiful but the glass floor was out of service. The hotel was close to Michigan Ave so heading to stores was a breeze. Overall, had an amazing time with my partner and would recommend reserving a room at this establishment.

Reviewed on 10 Apr 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was £1,964, price is now £1,357 per person
£1,357
per person
11 May - 18 May
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Very friendly staff, great location.

Reviewed on 6 Apr 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,725, price is now £1,224 per person
£1,224
per person
11 May - 18 May
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,357 reviews)
The staff is helpful. The room is a little bit old.

Reviewed on 10 Apr 2026

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

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
Fully refundableReserve now, pay when you stay
The price is £101 per night from 26 Apr to 27 Apr
£101
26 Apr - 27 Apr
includes taxes & fees
8/10 Very Good! (10,079 reviews)
Parking was terrible and extremely expensive

Reviewed on 10 Apr 2026

Congress Plaza 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 £120 per night from 26 Apr to 27 Apr
£120
26 Apr - 27 Apr
includes taxes & fees
9/10 Wonderful! (4,092 reviews)
It was nice

Reviewed on 10 Apr 2026

Hilton Chicago/Magnificent Mile Suites
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 £136 per night from 19 Apr to 20 Apr
£136
19 Apr - 20 Apr
includes taxes & fees
8.6/10 Excellent! (5,831 reviews)
Perfect location for a family trip, the hotel amenities were amazing and the staff was very friendly. We did have an issue with having our room serviced during our stay, after a long day out we came back to it still not being serviced, after asking the front desk they said they would put in the request ...

Reviewed on 9 Apr 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,790 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 £1,077. 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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Flyover in Chicago

Flyover in Chicago

£29
per adult
98% of travellers recommend
Flyover in 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. Flight-inclusive packages are ATOL protected.