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New Chicago Vacations from $330

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The Latest New Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Deluxe Studio Suite | Desk, laptop workspace, WiFi (free), bed sheets
    Sep 4 - Sep 8

    Encore Inn Inglewood + Flight

    Lockhaven
    4 nights
    2.5 star property
    6.4/10 - (183 reviews)
    "My room had termites. There were literally all over the bed. My face broke out. It was all over my personal belongings. It was horrible. The front desk clerk was very hesitant to change my rooms. The housekeeper had to come to the and then he moved me. O only stayed at night. O was so uncomfortable. This place was terrible."
    Reviewed July 6, 2026
    Roundtrip • Denver (DEN) - Los Angeles (LAX)
    DEN - LAX • Nonstop LAX - DEN • Nonstop
    $863
    $330
    per traveler
    found 1 day ago
    Encore Inn Inglewood
  • Front of property - evening/night
    Sep 3 - Sep 8

    SIRTAJ - Beverly Hills + Flight

    South of Wilshire
    5 nights
    4.0 star property
    8.2/10 - Very Good (1,001 reviews)
    "Close to Beverly hills."
    Reviewed July 18, 2026
    Roundtrip • Denver (DEN) - Los Angeles (LAX)
    DEN - LAX • Nonstop LAX - DEN • Nonstop
    $1,259
    $474
    per traveler
    found 1 day ago
    SIRTAJ - Beverly Hills
  • Jacuzzi, Non smoking | Living area
    Sep 4 - Sep 8

    Dream Inn + Flight

    Lockhaven
    4 nights
    3.0 star property
    7.0/10 - Good (72 reviews)
    Roundtrip • Denver (DEN) - Los Angeles (LAX)
    DEN - LAX • Nonstop LAX - DEN • Nonstop
    $1,370
    $589
    per traveler
    found 1 day ago
    Dream Inn
  • Exterior
    Aug 19 - Aug 23

    The Sofia Hotel + Flight

    Downtown San Diego
    4 nights
    3.5 star property
    8.6/10 - Excellent (2,389 reviews)
    Roundtrip • Dallas (DAL) - San Diego (SAN)
    DAL - SAN • Nonstop SAN - DAL • Nonstop
    $1,152
    $500
    per traveler
    found 1 day ago
    The Sofia Hotel
  • Desk, laptop workspace, iron/ironing board (on request), WiFi (free)
    Sep 26 - Oct 1

    Hyland Inn Near Legoland + Flight

    Olde Carlsbad
    5 nights
    3.0 star property
    7.8/10 - Good (1,007 reviews)
    Roundtrip • New York (JFK) - San Diego (SAN)
    JFK - SAN • Nonstop SAN - JFK • 1 stop
    Save 100% on your flight
    $1,163
    $547
    per traveler
    found 1 day ago
    Hyland Inn Near Legoland

New Chicago Hotel Deals

Lobby

Kiota Inn & Event Center Sutter Creek, an Ascend Collection Hotel

Kiota Inn & Event Center Sutter Creek, an Ascend Collection Hotel
3.0 star property
3.1 mi from New Chicago
8.6 out of 10, Excellent, (1,002 reviews)
"Nice and comfortable rooms."
$107 nightly
The price is $122
Aug 16 - Aug 17
Total with taxes and fees
Kiota Inn & Event Center Sutter Creek, an Ascend Collection Hotel
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.
See all properties in New Chicago

Frequently Asked Questions

How much does a New Chicago vacation package cost?

Offering excellent value package deals from $330 on Expedia, you'll be thrilled with how little a vacation to New Chicago costs! Expedia's packages simplify travel planning and maximize your savings.

What are the cheapest months to go to New Chicago?

You can usually find lower prices and greater availability in September, November and December. Take a look at our cheap New Chicago vacation packages and you could land some excellent off-season deals.

How many days is enough for New Chicago?

Typically, a handful of days is enough to check out the main sights during your New Chicago vacation. However, if you want to have time to rest or take day tours, think about extending your trip.

How to find the best New Chicago package deals?

Bagging a cheap New Chicago package deal is a breeze with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can tailor your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to view the most affordable New Chicago package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.

Is it cheaper to book a New Chicago vacation as a package?

You can enjoy significant savings on your New Chicago getaway by booking a customized vacation package. Click on the "Package" heading, then select your travel dates and destination to see some great hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.

When to book a vacation package to New Chicago?

If you're planning an impromptu New Chicago vacation, check out our last-minute deals that can be booked up to a 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.

Does Expedia offer Book Now, Pay Later New Chicago vacation packages?

Jet off on your dream escape to New Chicago with help from our Book Now, Pay Later vacations. No need to save up or wait until payday — we've joined forces with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans mean you can split the cost over 3, 6 or 12 months. With no hidden or late payment fees, you can easily stay on budget and snag great deals before they sell out.

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