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

Top New Chicago Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile
Hotel Riu Plaza Chicago
Hotel Felix River North/Magnificent Mile
Sable at Navy Pier Chicago, Curio Collection by Hilton
Trump International Hotel & Tower Chicago

Ready to book your vacation to New Chicago?

 

Choose your dates

New Chicago Hotel Deals

Days Inn and Suites by Wyndham Hammond, IN

Days Inn and Suites by Wyndham Hammond, IN

2 out of 5
4000 Calumet Avenue Hammond IN
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from Aug 31 to Sep 1
CA $134
CA $150 total
Aug 31 - Sep 1
includes taxes & fees
Days Inn and Suites by Wyndham Hammond, IN
Super 8 by Wyndham South Holland

Super 8 by Wyndham South Holland

2 out of 5
17225 Halsted St South Holland IL
Fully refundableReserve now, pay when you stay
The price is CA $95 per night from Sep 6 to Sep 7
CA $95
CA $107 total
Sep 6 - Sep 7
includes taxes & fees
7.6/10 Good! (1,186 reviews)
"Clean room was my most concern and it was spotless"

Reviewed on Aug 5, 2026

Super 8 by Wyndham South Holland
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

4 out of 5
777 Ameristar Blvd. East Chicago IN
Fully refundableReserve now, pay when you stay
The price is CA $146 per night from Aug 30 to Aug 31
CA $146
CA $181 total
Aug 30 - Aug 31
includes taxes & fees
Ameristar Casino Hotel East 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.

Frequently asked questions

How much does a New Chicago vacation package cost?
You can snap up a vacation package to this destination from CA $710 on Expedia. However, how much your vacation to New Chicago costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to New Chicago?
If you're hoping to score a cheap New Chicago vacation package, consider travelling in January, February and September. You'll generally find better prices on flights and hotels during these months — ideal for budget-conscious travellers.
How many days is enough for New Chicago?
The ideal duration for your New Chicago vacation depends on what you'd like to do and see. Usually, a few days to a week will give you enough time to go to all the top attractions and explore some hidden gems along the way.
How to find the best New Chicago package deals?
Start your search for a New Chicago package deal by entering your travel dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect New Chicago package deal right away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your New Chicago escape underway.
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 tailored vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to New Chicago?
If you're planning a spontaneous New Chicago trip, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to New Chicago?

  1. Choose the best time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit New Chicago.
  2. Figure out your budget: Ensure you have enough money to cover everything from food and transportation to activities and flights. Your accommodations will likely be the largest expense during your trip to New Chicago.
  3. Work out your trip length: Consider how much time you'd like to spend discovering New Chicago. Plan your itinerary so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a personalized 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.