Little Italy Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 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

    Packages with flights are ATOL protected

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.
  • Smart TV
    Jul 4 - Jul 11

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    7 nights
    4.0 star property
    9.2/10 - Wonderful (488 reviews)
    "Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely."
    Reviewed May 22, 2026
    Return • Aberdeen (ABZ) - Chicago (ORD)
    ABZ - ORD • 1 stop ORD - ABZ • 1 stop
    £2,037
    £1,457
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • Premium bedding, pillow-top beds, in-room safe, individually furnished
    Jul 4 - Jul 11

    Level Chicago - River North + Flight

    Downtown Chicago
    7 nights
    4.0 star property
    9.2/10 - Wonderful (1,010 reviews)
    "I loved everything."
    Reviewed May 25, 2026
    Return • Aberdeen (ABZ) - Chicago (ORD)
    ABZ - ORD • 1 stop ORD - ABZ • 1 stop
    Save 100% on your flight
    £3,557
    £2,423
    per traveller
    found 1 day ago
    Level Chicago - River North
  • Full-sized fridge, microwave, oven, stovetop
    Jul 4 - Jul 11

    Level Chicago – Old Town + Flight

    Downtown Chicago
    7 nights
    4.0 star property
    9.0/10 - Wonderful (481 reviews)
    "Nice and big"
    Reviewed May 24, 2026
    Return • Aberdeen (ABZ) - Chicago (ORD)
    ABZ - ORD • 1 stop ORD - ABZ • 1 stop
    £2,220
    £1,640
    per traveller
    found 1 day ago
    Level Chicago – Old Town
  • Terrace/patio
    Jul 4 - Jul 11

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    7 nights
    5.0 star property
    9.6/10 - Exceptional (1,882 reviews)
    "Excellent"
    Reviewed May 21, 2026
    Return • Aberdeen (ABZ) - Chicago (ORD)
    ABZ - ORD • 1 stop ORD - ABZ • 1 stop
    £2,896
    £2,185
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago
  • Terrace/patio
    Jul 4 - Jul 11

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    7 nights
    4.0 star property
    9.4/10 - Exceptional (2,513 reviews)
    "Beautiful views and amazing amenities"
    Reviewed May 25, 2026
    Return • Aberdeen (ABZ) - Chicago (ORD)
    ABZ - ORD • 1 stop ORD - ABZ • 1 stop
    £2,149
    £1,623
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton

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 £118 per night from 27 May to 28 May
£118
27 May - 28 May
includes taxes & fees
8/10 Very Good! (10,140 reviews)
"tiniest room i’ve ever stayed in and shower leaked all over the floor and"

Reviewed on 25 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £205 per night from 26 May to 27 May
£205
26 May - 27 May
includes taxes & fees
9.4/10 Exceptional! (4,246 reviews)
"Nice room and great breakfast Roof deck has a great view"

Reviewed on 25 May 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is £107 per night from 27 May to 28 May
£107
27 May - 28 May
includes taxes & fees
7.8/10 Good! (1,472 reviews)
"Staff was extremely helpful!"

Reviewed on 25 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,722 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 . 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
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

£16
per child
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.