New City Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

    Plan, book, and manage your trip all in one place

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 which includes 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

Top hotels in New City

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is S$268 per night from 4 Aug to 5 Aug
S$268
4 Aug - 5 Aug
includes taxes & fees
7.8/10 Good! (8,909 reviews)
A Gem on Michigan Ave
"I was surprised at how nice my room was in this older building. The view of Buckingham fountain and the lake was the best. I was able to watch navy pier fireworks. Just an absolute pleasure and I will return!!!"

Reviewed on 21 Jul, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is S$417 per night from 24 Jul to 25 Jul
S$417
24 Jul - 25 Jul
includes taxes & fees
9/10 Wonderful! (2,071 reviews)
"Great location!"

Reviewed on 19 Jul, 2025

InterContinental Chicago Magnificent Mile by IHG
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 S$217 per night from 17 Aug to 18 Aug
S$217
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (2,482 reviews)
"The staff was very helpful"

Reviewed on 19 Jul, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,699 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 holiday package cost?
From just . 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 holiday 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 holiday?
Savvy travellers 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 organising 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 holiday package?
With a holiday 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 holiday 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.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

4.5/5(147 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

Things to do

River tour boat in Chicago

Architecture River Tour

S$53
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

S$52
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

S$58
per adult
94% 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.