New Chicago Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Your New Chicago Vacation

When a city stay is calling your name, answer it with a New Chicago vacation package. With all your travel plans in place before you leave, all you need to do here is concentrate on having fun. Eager to do some sightseeing but not sure where to begin? Any trip to New Chicago should include Drytown Cellars. Stop daydreaming and start traveling. Browse the broad range of options on Expedia today and finally put your New Chicago vacation plans in motion!

Top New Chicago Vacation Deals

Price found within the past 48 hours. Click for updated prices.
SIRTAJ - Beverly Hills

SIRTAJ - Beverly Hills

4 out of 5
South of Wilshire
Price was CA $2,023, price is now CA $1,023 per person
CA $1,023
per person
Jan 9 - Jan 15
found 5 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Los Angeles (LAX)
8.2/10 Very good! (1,005 reviews)

The Sofia Hotel

The Sofia Hotel

3.5 out of 5
Downtown San Diego
Price was CA $2,069, price is now CA $1,066 per person
CA $1,066
per person
Jan 12 - Jan 19
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to San Diego (SAN)
8.8/10 Excellent! (2,743 reviews)
It was great. Would come back any time

Reviewed on Nov 4, 2026

The Historic Broadlind Hotel at Long Beach Convention Center

The Historic Broadlind Hotel at Long Beach Convention Center

3 out of 5
Downtown Long Beach
Save 100% on your flight
Price was CA $3,795, price is now CA $2,111 per person
CA $2,111
per person
Dec 13 - Dec 20
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Los Angeles (LAX)
7.6/10 Good! (966 reviews)

Hotel Z

Hotel Z

3 out of 5
Downtown San Diego
Save 100% on your flight
Price was CA $1,897, price is now CA $1,150 per person
CA $1,150
per person
Jan 26 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to San Diego (SAN)
9.2/10 Wonderful! (1,212 reviews)
Nice place

Reviewed on Nov 3, 2026

1 Hotel West Hollywood

1 Hotel West Hollywood

5 out of 5
West Hollywood
Price was CA $4,451, price is now CA $2,714 per person
CA $2,714
per person
Jan 9 - Jan 15
found 5 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Los Angeles (LAX)
8.8/10 Excellent! (1,005 reviews)

Ready to book your vacation to New Chicago?

 

Choose your dates

New Chicago Hotel Deals

Red Hawk Resort & Casino

Red Hawk Resort & Casino

4 out of 5
1 Red Hawk Pkwy Placerville CA
Fully refundableReserve now, pay when you stay
The price is CA $236 per night from Nov 17 to Nov 18
CA $236
CA $260 total
Nov 17 - Nov 18
includes taxes & fees
9.4/10 Exceptional! (682 reviews)
"First time here at this location resort was amazed how clean and nice the service. Especially the bellman. He took his time to explain everything I should know about the room and amenities. Will be back when I’m in town again."

Reviewed on Nov 5, 2026

Red Hawk Resort & Casino
Studio 6 Suites Cameron Park, CA – Folsom

Studio 6 Suites Cameron Park, CA – Folsom

2 out of 5
3444 Coach Ln Shingle Springs CA
Fully refundableReserve now, pay when you stay
The price is CA $120 per night from Nov 10 to Nov 11
CA $120
CA $132 total
Nov 10 - Nov 11
includes taxes & fees
Studio 6 Suites Cameron Park, CA – Folsom
Best Western Amador Inn

Best Western Amador Inn

2.5 out of 5
200 S State Highway 49 Jackson CA
Fully refundableReserve now, pay when you stay
The price is CA $117 per night from Nov 15 to Nov 16
CA $117
CA $131 total
Nov 15 - Nov 16
includes taxes & fees
Best Western Amador Inn
See all 231 properties in New 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a New Chicago vacation package cost?
Offering excellent value package deals from CA $1,023 on Expedia, you'll be thrilled with how little a vacation to New Chicago costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to New Chicago?
January, February and November are the best times to look for cheap New Chicago vacation packages. Choosing to travel in less busy periods means you can generally find lower prices on hotels and flights.
How many days is enough for New Chicago?
The ideal duration for your New Chicago vacation depends on what you'd like to see and do. Typically, a handful of days to a week will give you plenty of time to hit all the top attractions and explore some hidden spots along the way.
How to find the best New Chicago package deals?
Begin your search for a New Chicago package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect New Chicago package deal right away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your New Chicago adventure underway.
Is it cheaper to book a New Chicago vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging hotels and flights individually. Better still, you can personalize your New Chicago escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to New Chicago?
If you're considering a spontaneous New Chicago adventure, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to New Chicago?

  1. Choose your dates: The things you want to do in New Chicago and your favourite season can help you decide when to go.
  2. Plan your budget wisely: As well as the price of your stay, you'll need to factor in other expenses. These include food, flights and transportation. Also, put aside some extra funds for unexpected expenses that may crop up during your trip to New Chicago.
  3. Decide your trip length: Think about how long you want to spend discovering New Chicago. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a tailored New Chicago vacation package.

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