Little Italy Holidays

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    Save up to €900 when you book a flight and hotel together*

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

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Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Jun 25 - Jul 3

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    8 nights
    4.0 star property
    8.2/10 - Very good (2,721 reviews)
    "Great location and helpful staff. Small rooms and public areas."
    Reviewed May 25, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    €1,730
    €1,195
    per traveller
    found 1 day ago
    Hotel Felix River North/Magnificent Mile
  • Smart TV
    Jun 25 - Jul 3

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    8 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 • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    Save 100% on your flight
    €2,063
    €1,298
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • View from property
    Jun 25 - Jul 3

    The Talbott, Autograph Collection + Flight

    Downtown Chicago
    8 nights
    4.5 star property
    9.4/10 - Exceptional (117 reviews)
    "We thoroughly enjoyed our stay. The location was excellent, conveniently close to everything we needed. The room was spacious and spotless. The breakfast was fantastic, offering a wide variety of options to choose from. "
    Reviewed May 17, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    Save 100% on your flight
    €2,174
    €1,545
    per traveller
    found 1 day ago
    The Talbott, Autograph Collection
  • 2 restaurants; breakfast, lunch, and dinner served
    Jun 25 - Jul 3

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    8 nights
    4.5 star property
    9.4/10 - Exceptional (3,725 reviews)
    "Super location, good crowd of staff and fellow travellers. Smells great!"
    Reviewed May 24, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    Save 100% on your flight
    €1,955
    €1,389
    per traveller
    found 1 day ago
    LondonHouse Chicago, Curio Collection by Hilton
  • Exterior
    Jun 25 - Jul 3

    Hilton Garden Inn Chicago Downtown Riverwalk + Flight

    Downtown Chicago
    8 nights
    3.0 star property
    9.0/10 - Wonderful (1,937 reviews)
    "Front desk staff are cheerful and helpful. Checking was a breeze. On our 4 night stay our room was immaculately clean when we returned from our day's activities."
    Reviewed May 24, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    Save 100% on your flight
    €2,071
    €1,490
    per traveller
    found 1 day ago
    Hilton Garden Inn Chicago Downtown Riverwalk

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 €137 per night from 26 May to 27 May
€137
26 May - 27 May
includes taxes & fees
8/10 Very Good! (10,138 reviews)
"Good"

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 €269 per night from 16 Jun to 17 Jun
€269
16 Jun - 17 Jun
includes taxes & fees
9.4/10 Exceptional! (4,238 reviews)
"Solo traveler. Spacious king room. Double sink bathroom. The breakfast buffett was one of the best I've had. Convenient location to Michigan Ave and Riverwalk."

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 €156 per night from 27 May to 28 May
€156
27 May - 28 May
includes taxes & fees
7.8/10 Good! (1,467 reviews)
"Complimentary breakfast was really nice."

Reviewed on 24 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,724 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 . 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

Tri Taylor

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 acclaimed theatre scene in this vibrant area.

University of Illinois Chicago

Credit Union 1 Arena

Catch an event at Credit Union 1 Arena during your trip to Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area.

Credit Union 1 Arena

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€23
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

€38
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€39
per adult
100% of travellers recommend
Chicago Sightseeing River and 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.