Little Italy Holidays

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Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Jul 14 - Jul 26

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    12 nights
    4.0 star property
    8.2/10 - Very good (2,770 reviews)
    "Staff was friendly and hotel was very clean! It’s in a great location and we enjoyed our room a lot! I took off a point because when we asked for fresh towels, they never came to our room and we had to ask again. But overall very comfortable and pleasant stay!"
    Reviewed June 7, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$7,339
    NZ$5,025
    per traveller
    found 7 hours ago
    Hotel Felix River North/Magnificent Mile
  • Smart TV
    Jul 14 - Jul 26

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    12 nights
    4.0 star property
    9.2/10 - Wonderful (493 reviews)
    "Fully equipmet"
    Reviewed June 2, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    Save 100% on your flight
    NZ$8,374
    NZ$5,408
    per traveller
    found 7 hours ago
    Level Chicago Fulton Market
  • 2 restaurants; breakfast, lunch and dinner served
    Jul 14 - Jul 26

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    12 nights
    4.5 star property
    9.4/10 - Exceptional (3,732 reviews)
    "We stayed in this hotel in our daughter's wedding weekend. It was wonderful, the river and city view from our 18th story room was spectacular. I recommend it to.all ages."
    Reviewed June 7, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    Save 100% on your flight
    NZ$10,218
    NZ$6,821
    per traveller
    found 7 hours ago
    LondonHouse Chicago, Curio Collection by Hilton
  • Terrace/patio
    Jul 14 - Jul 26

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

    Downtown Chicago
    12 nights
    4.0 star property
    9.4/10 - Exceptional (2,529 reviews)
    "All elevators to the 6th floor were not working due to some apparent flooding. Carrying suitcases up 5 flights for a family of four was exhausting. They offered a $60 food voucher at the restaurant. The room had 2 towels despite notifying them that we were a family of four. The view was great, but the curtains did not close so the room was not very dark all night from the navy pier lights."
    Reviewed June 8, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    Save 100% on your flight
    NZ$7,904
    NZ$5,443
    per traveller
    found 7 hours ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Breakfast and dinner served
    Jul 14 - Jul 26

    Omni Chicago Hotel + Flight

    Downtown Chicago
    12 nights
    4.5 star property
    9.2/10 - Wonderful (1,793 reviews)
    "Harry Pooter touch was the best!!"
    Reviewed June 7, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$7,911
    NZ$5,558
    per traveller
    found 7 hours ago
    Omni Chicago Hotel

Our guide on 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

Our pick of the best Little Italy Hotel Deals

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 NZ$279 per night from 29 June to 30 June
NZ$279
29 June - 30 June
includes taxes & fees
8/10 Very Good! (10,202 reviews)
"Just didn’t feel nice enough for the price"

Reviewed on 8 June 2026

Congress Plaza Hotel
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 NZ$312 per night from 28 June to 29 June
NZ$312
28 June - 29 June
includes taxes & fees
7.8/10 Good! (1,536 reviews)
"The property was good, no pool which is fine for us. Read that there was a hidden mandatory fee but book with Expedia and that was not the case. Card didn’t open the door to the hotel room on 2 occasions but that was the only hiccup"

Reviewed on 8 June 2026

The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is NZ$313 per night from 28 June to 29 June
NZ$313
28 June - 29 June
includes taxes & fees
8.8/10 Excellent! (2,629 reviews)
"Good hotel for family and business trips. Conveniently located near O’Hare. Courteous staff and people of Chi."

Reviewed on 7 June 2026

Hyatt Regency O'Hare Chicago
See all 4,683 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.

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$45
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

NZ$77
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
Art Institute of Chicago

Art Institute of Chicago

NZ$67
per adult
92% of travellers recommend
Art Institute of 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.