New City Vacations from ￥210,174

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The Latest New City Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was ￥265,634, price is now ￥210,174 per person
￥210,174
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (2,027 reviews)
The property is Great I got married there!

Reviewed on Sep 24, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥343,518, price is now ￥246,906 per person
￥246,906
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
The hotel was great but we were hit with an unexpected $50 charge at checking that wasn’t noted when booking the room. I might have chosen a different hotel if I had known about this charge. It kinda ruined my thoughts on the hotel, but overall the experience was positive

Reviewed on Sep 25, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥399,230, price is now ￥289,662 per person
￥289,662
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
The hotel was above the expectations and river view was fabulous also staff were incredibly awesome specially the front dest employee Natalia she was helpful, smiling and welcoming.

Reviewed on Sep 24, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was ￥326,194, price is now ￥242,014 per person
￥242,014
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The room was perfect and the front staff were exceptional. Our stay was amazing!

Reviewed on Sep 21, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was ￥304,646, price is now ￥239,497 per person
￥239,497
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
I was so disappointed in my stay at the Emily. For almost $500/night I was expecting nice, spacious rooms. The room was so small, the sink was in the hallway, the bed was so uncomfortable, dingy design. I’ve stayed at better Aloft or Moxy rooms. The food at Fora, the hotel restaurant, is uninspired and unseasoned. The brunch chiliques were bland. Skip this hotel in west loop and stay at the hoxton instead

Reviewed on Sep 22, 2025

Where to stay in New City

Find the best New City areas and neighborhoods for the activities you enjoy most. Learn more about New City
Downtown Chicago showing a city

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

New City 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 ￥19,991 per night from Oct 26 to Oct 27
￥19,991
￥23,468 total
Oct 26 - Oct 27
includes taxes & fees
7.8/10 Good! (9,307 reviews)
"Parking situation is ridicules, hallways carpet very filthy. I understand it’s an older hotel but needs to be kept up. Bathroom door didn’t even close."

Reviewed on Sep 25, 2025

Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥15,863 per night from Oct 20 to Oct 21
￥15,863
￥21,241 total
Oct 20 - Oct 21
includes taxes & fees
7.8/10 Good! (2,387 reviews)
"It felt cozy and comfortable. The room was a little bit dusty and the night light was not working."

Reviewed on Sep 24, 2025

Freehand Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥23,908 per night from Oct 20 to Oct 21
￥23,908
￥28,067 total
Oct 20 - Oct 21
includes taxes & fees
8.8/10 Excellent! (2,946 reviews)
"This hotel was clean and the staff was very helpful and friendly. Parking is expensive, but that’s the case everywhere in Chicago. The view of the lake and surrounding buildings is very nice! The location is excellent and easy walking distance to everything you want to do in Chicago."

Reviewed on Sep 24, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,640 properties in New City
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 New City vacation package cost?
From just ￥210,174. Yes, you read that right. Our New City packages are the easiest way to stretch your budget further. Bundle your preferred hotels, flights and car rentals and discover this wonderful destination.
How do I get a cheap travel package to New City?
Just imagine all the amazing things you could do in New City with extra cash in your pocket. Watch your savings stack up when you bundle your hotel and flights into a New City vacation package. You have plenty of choice when it comes to booking with Expedia too. In fact, you can choose from over 550 airlines and 1,000,000 hotel options around the globe. Whether you're taking a break with the entire family or flying solo, exploring New City is better with a package.
Where should I stay in New City?
We recommend staying near the action. Many people book hotels within easy reach of top sights, such as St. Bernard Hospital, S.S. Peter and Paul Church and Holy Cross Hospital.
How far in advance should I book my New City vacation?
Savvy travelers will likely want to book as early as possible. You can normally browse through international airfares on Expedia up to 12 months before your flight. If you're purchasing your ticket at the last minute, don't despair. Bargain prices sometimes occur just weeks prior to departure.
What does an Expedia New City travel package include?
Rental cars, hotels and flights, or any combination of them — it's your choice. Whether you're visiting New City with the entire family or enjoying a solo break, there's a package to match every budget and style. Once you've made your booking, why not add on a few tours and experiences?
What should I know before booking a New City travel package?
You'll enjoy amazing savings when you bundle your flights, hotels and rental cars into a travel package. Plus, booking everything in one spot just makes things easier. So why waste money or time? Whether you're organizing a ritzy city getaway or an affordable family break, take a look at our package deals today.
Can I choose my airline with a New City Expedia vacation package?
With a vacation package, you're in charge. Whether you're looking to fly to New City in coach or first class, simply pick from the available airline options. Expedia has access to over 550 partner airlines globally.
If I'm not able to travel, can I cancel my New City vacation package?
If your travel plans in New City have been upended, it's a relief to know that it's possible to amend or cancel your booking. If you made your booking within the last 24 hours, you may be eligible to receive a refund. If your booking is older than that, your hotel, airline or car rental company may impose fees. To find out more, check our Customer Service Portal.

Discover the most popular places to visit in New City

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

￥7,144
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥6,633
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

￥6,633
per adult
96% of travellers recommend
Chicago By Night River & 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.