Little Italy Vacations

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  • Better together

    Save up to ¥109,000 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.
  • Jul 9 - Jul 20

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    11 nights
    4.0 star property
    8.2/10 - Very Good (2,757 reviews)
    "The staff were friendly and helpful."
    Reviewed June 5, 2026
    Roundtrip Tokyo (HND) - Chicago (ORD)
    HND - ORD1 stop ORD - NRT1 stop
    ¥664,976
    ¥515,076
    per traveler
    found 17 hours ago
    Hotel Felix River North/Magnificent Mile
  • Jul 9 - Jul 20

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    11 nights
    4.0 star property
    9.4/10 - Exceptional (4,349 reviews)
    "Everyone was very polite and the hotel was very clean."
    Reviewed June 5, 2026
    Roundtrip Tokyo (HND) - Chicago (ORD)
    HND - ORD1 stop ORD - NRT1 stop
    ¥788,655
    ¥547,408
    per traveler
    found 17 hours ago
    Hotel Riu Plaza Chicago
  • Jul 9 - Jul 20

    Omni Chicago Hotel + Flight

    Downtown Chicago
    11 nights
    4.5 star property
    9.2/10 - Wonderful (1,789 reviews)
    "Booked a room - got a suite! Enjoyed the extra space. A separate living room for watching TV or working at a desk. Staff at the hotel was very helpful. Enjoyed the breakfast too."
    Reviewed June 3, 2026
    Roundtrip Tokyo (HND) - Chicago (ORD)
    HND - ORD1 stop ORD - NRT1 stop
    ¥658,901
    ¥526,351
    per traveler
    found 17 hours ago
    Omni Chicago Hotel
  • Jul 9 - Jul 20

    Eurostars Magnificent Mile + Flight

    Downtown Chicago
    11 nights
    4.0 star property
    9.0/10 - Wonderful (3,605 reviews)
    "The hotel staff was very friendly and inviting on all shifts. Also the parking garage is two blocks down from the hotel which wasn’t a problem for me but plan accordingly. The room was very clean and house keeping dose a nice job tidying up during the stay. Very close to all attractions. Also the view of the city is everything you could hope for!"
    Reviewed June 3, 2026
    Roundtrip Tokyo (HND) - Chicago (ORD)
    HND - ORD1 stop ORD - NRT1 stop
    ¥639,677
    ¥522,158
    per traveler
    found 17 hours ago
    Eurostars Magnificent Mile
  • Jul 9 - Jul 20

    Arlo Chicago + Flight

    Downtown Chicago
    11 nights
    4.0 star property
    9.4/10 - Exceptional (2,124 reviews)
    "Loved this location and eager to try other Arlo’s in other states"
    Reviewed June 5, 2026
    Roundtrip Tokyo (HND) - Chicago (ORD)
    HND - ORD1 stop ORD - NRT1 stop
    ¥673,159
    ¥557,585
    per traveler
    found 17 hours ago
    Arlo Chicago

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

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 ¥22,322 per night from Jun 29 to Jun 30
¥22,322
¥26,539 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,175 reviews)
"We had a clean room, the staff was attentive. It was a great experience!"

Reviewed on Jun 5, 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 ¥24,305 per night from Jun 28 to Jun 29
¥24,305
¥28,896 total
Jun 28 - Jun 29
includes taxes & fees
7.8/10 Good! (1,520 reviews)
"👍"

Reviewed on Jun 5, 2026

The Chicago Hotel Collection - Magnificent Mile
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 ¥30,243 per night from Jun 30 to Jul 1
¥30,243
¥40,517 total
Jun 30 - Jul 1
includes taxes & fees
9.4/10 Exceptional! (4,349 reviews)
"Everyone was very polite and the hotel was very clean."

Reviewed on Jun 5, 2026

Hotel Riu Plaza Chicago
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 vacation package cost?
From as little as . Yes, you read that correctly. Our Little Italy vacation 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 vacation 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 Center. 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 travelers.
How far in advance should I book my Little Italy vacation?
Travelers 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 vacation is just clicks away.
Can I choose my airline with a Little Italy Expedia vacation package?
With a vacation 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 vacation package?
If your vacation 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.

Discover the most popular places to visit in Little Italy

Things to do

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.