New City Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in New City
Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
CA $1,152
per person
Jan 3 - Jan 9
found 16 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.6/10 Excellent! (1,015 reviews)
We had an early arrival, and first had only planned to store the luggage. Very friendly at reception had a nice surprise that rooms were already available - no extra costs.
All staff was very attentive,
Reviewed on Oct 18, 2026
Level Chicago Fulton Market
Downtown Chicago
CA $1,122
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (576 reviews)
El edificio es muy bueno, la atención del personal pésimo, siempre mal predispuestos para ayudar!
Reviewed on Oct 17, 2026
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
4 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.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
New City Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $148
CA $176 total
Nov 11 - Nov 12
includes taxes & fees
8/10 Very good! (10,141 reviews)
"The location is spectacular! The lobby is beautiful with historic charm. Our room was updated and modern. I’d stay here again!"
Reviewed on Oct 18, 2026
River Hotel
75 East Wacker Drive Chicago IL
CA $215
CA $256 total
Nov 1 - Nov 2
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $171
CA $203 total
Nov 11 - Nov 12
includes taxes & fees
8/10 Very good! (2,524 reviews)
"This is an old hotel with small elevators old stairwells which don't have handrails on both sides. the rooms are nice."
Reviewed on Oct 18, 2026
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 CA $1,063. 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.
Stay near popular New City attractions
Union Stock Yard Gate
You can find out about the history of Chicago with a trip to Union Stock Yard Gate.
Things to do
Skydeck Chicago at Willis Tower
CA $59
per adult
88% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.