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New Chicago Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

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

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

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Top New Chicago vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Deluxe Quadruple Room, 2 Double Beds
    Sept 4 - Sept 7

    Encore Inn Inglewood + Flight

    Lockhaven
    3 nights
    2.5 star property
    6.4/10 - (197 reviews)
    "it was dirty. There was hair in the shower. The fridge was dirty. The floors are dirty. There was roaches, and even the mattress has stains."
    Reviewed August 4, 2026
    Roundtrip • Toronto (YTO) - Los Angeles (LAX)
    YYZ - LAX • Nonstop LAX - YYZ • Nonstop
    CA $1,323
    CA $716
    per traveller
    found 1 day ago
    Encore Inn Inglewood
  • Front of property - evening/night
    Sept 14 - Sept 20

    SIRTAJ - Beverly Hills + Flight

    South of Wilshire
    6 nights
    4.0 star property
    8.2/10 - Very good (1,010 reviews)
    Roundtrip • Edmonton (YEG) - Los Angeles (LAX)
    YEG - LAX • 1 stop LAX - YEG • 1 stop
    CA $2,444
    CA $1,220
    per traveller
    found 1 day ago
    SIRTAJ - Beverly Hills
  • Exterior
    Sept 6 - Sept 10

    The Sofia Hotel + Flight

    Downtown San Diego
    4 nights
    3.5 star property
    8.6/10 - Excellent (2,470 reviews)
    "Historically Classy!"
    Reviewed August 5, 2026
    Roundtrip • Edmonton (YEG) - San Diego (SAN)
    YEG - SAN • 1 stop SAN - YEG • 1 stop
    CA $1,755
    CA $999
    per traveller
    found 16 hours ago
    The Sofia Hotel
  • Comfort Room, 1 Queen Bed, Non Smoking | Terrace/patio
    Sept 21 - Sept 27

    The LEEF Hotel + Flight

    Citrus Grove
    6 nights
    2.0 star property
    8.6/10 - Excellent (786 reviews)
    "The Leef was so cute. Very clean. Super comfy bed. AC worked well which was a blessing on a 100 degree day. The TV is mounted on the wall and swings out in a really nifty way. It was alao nice a quiet. The check in process with the lobby person on a screen was really interesting. Different but it worked well. And I 😘 bed the code for the door instead of a key. No key to lose! I would stay here again in a heartbeat"
    Reviewed August 4, 2026
    Roundtrip • Edmonton (YEG) - Los Angeles (LAX)
    YEG - LAX • 2 stops LAX - YEG • 1 stop
    CA $1,540
    CA $905
    per traveller
    found 1 day ago
    The LEEF Hotel
  • Couples treatment rooms, sauna, steam room, body treatments
    Oct 13 - Oct 18

    The Huntington Hotel + Flight

    Downtown San Francisco
    5 nights
    5.0 star property
    9.4/10 - Exceptional (28 reviews)
    "I have not experienced this level of service in San Francisco anywhere else. The staff was friendly, helpful and went above and beyond to make us feel welcome. From ensuring we had rides, reservations and the necessary infrastructure to conduct work from the hotel to the little touches of dropping of fresh flowers and providing yummy treats throughout our stay -- everything was so carefully crafted and thought through. And the views, interiors and food were delicious. To bring this home, when i..."
    Reviewed July 29, 2026
    Roundtrip • Vancouver (YVR) - San Francisco (SFO)
    YVR - SFO • Nonstop SFO - YVR • Nonstop
    CA $4,025
    CA $2,408
    per traveller
    found 1 day ago
    The Huntington Hotel

New Chicago Hotel Deals

Outdoor pool

Oak Ridge Inn

Oak Ridge Inn
2.5 star property
3.6 km from New Chicago
8.6 out of 10, Excellent, (328 reviews)
"While the property was clean, when we arrived and checked into the room, our room was so hot, you’d think, since they knew they were having people stay in this room, they’d turn on the air, but no. We had to turn on the air and leave for awhile. Thankfully, it cooled, but not a great start. And if your a person, like myself and my family, we don’t like to wake up to a bright room- the curtains were so thin, the room was so bright, we couldn’t sleep. So, definitely will not be returning."
The price is CA $176
CA $197 total
includes taxes & fees
Aug 17 - Aug 18
Oak Ridge Inn
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 CA $716 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.