Little Italy Holidays from £1,216

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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.
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Price was £1,625, price is now £1,216 per person
£1,216
per person
11 Sept - 16 Sept
found 24 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,388 reviews)
We originally had room 2101 and the ac or mini fridge didn’t work so we were given another room 1601 and everything worked. Trip was great.

Reviewed on 9 Jul 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,035, price is now £1,325 per person
£1,325
per person
11 Sept - 16 Sept
found 24 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.

Reviewed on 9 Jul 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,852, price is now £1,238 per person
£1,238
per person
11 Sept - 16 Sept
found 24 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Amazing and beautiful hotel with caring and helpful staff!

Reviewed on 8 Jul 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,890, price is now £1,386 per person
£1,386
per person
1 Oct - 6 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Front desk staff was super helpful and enthusiastic. Smooth check-in, and checkout.

Reviewed on 8 Jul 2026

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was £1,928, price is now £1,446 per person
£1,446
per person
11 Sept - 16 Sept
found 24 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,251 reviews)
Viceroy staff were

Reviewed on 7 Jul 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
A busy city street with tall buildings, a bus, and cars.

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 Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is £136 per night from 27 Jul to 28 Jul
£136
27 Jul - 28 Jul
includes taxes & fees
8.2/10 Very good! (1,725 reviews)
"We were happy to be given a room before check in time, but the one we were given was dirty and not cleaned from the previous person. We were given another room which worked out fine. We enjoyed that it was historic but renovated for the most part. The downfall was that we could hear the neighbors ..."

Reviewed on 9 Jul 2026

The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is £209 per night from 9 Aug to 10 Aug
£209
9 Aug - 10 Aug
includes taxes & fees
9.2/10 Wonderful! (1,894 reviews)
"It was an amazing hotel!"

Reviewed on 9 Jul 2026

Omni Chicago 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 £164 per night from 6 Aug to 7 Aug
£164
6 Aug - 7 Aug
includes taxes & fees
8/10 Very good! (10,217 reviews)
"Our stay was great, best was comfortable and room was clean."

Reviewed on 9 Jul 2026

Congress Plaza Hotel
See all 4,490 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
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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 £1,216. 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.

Stay near popular Little Italy attractions

University of Illinois Chicago

8.4/10 (1,058 reviews)
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.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£19
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£31
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture 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. Flight-inclusive packages are ATOL protected.