New Chicago Vacations from ￥240,237

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The Latest New Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Sep 18 - Sep 24
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Nice hotel with a great breakfast buffet

Reviewed on Jul 25, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
The property in itself was not terrible, but I expected better.

Reviewed on Jul 19, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Very nice amenities and food. We would come back to this property

Reviewed on Jul 25, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on Jul 22, 2025

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
per person
Oct 8 - Oct 12
found 5 hours ago
Roundtrip flight included
Nagoya (NGO) to Chicago (ORD)
9.4/10 Exceptional! (1,011 reviews)
Great staff and services!

Reviewed on Jul 23, 2025

Find the Best New Chicago Vacation Packages

New Chicago Hotel Deals

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 ￥16,589 per night from Aug 4 to Aug 5
￥16,589
￥20,049 total
Aug 4 - Aug 5
includes taxes & fees
8.4/10 Very Good! (1,024 reviews)
"Great"

Reviewed on Jul 24, 2025

Ameristar Casino Hotel East Chicago
Spring House Inn

Spring House Inn

2.5 out of 5
303 N Mineral Springs Rd, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is ￥19,052 per night from Aug 18 to Aug 19
￥19,052
￥21,338 total
Aug 18 - Aug 19
includes taxes & fees
8.8/10 Excellent! (1,015 reviews)
"Nestled in the woods it was a nice place to stay. The room was very clean and the staff were very friendly."

Reviewed on Jul 24, 2025

Spring House Inn
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 ￥11,252 per night from Aug 4 to Aug 5
￥11,252
￥12,713 total
Aug 4 - Aug 5
includes taxes & fees
7.4/10 Good! (1,024 reviews)
"The room was comfortable, clean and quiet. The only problem I had was the hot water pressure was low in the sink."

Reviewed on Jul 21, 2025

Super 8 by Wyndham South Holland
See all 479 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.

Frequently asked questions

How much does a New Chicago vacation package cost?
You can snap up a vacation package to this destination from ￥240,237 on Expedia. But how much your vacation to New Chicago costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to New Chicago?
January, February and September are great times to look for cheap New Chicago vacation packages. Traveling in quieter months means you can usually find lower prices on flights and hotels.
How many days is enough for New Chicago?
With a well-organized schedule, you can easily visit the top New Chicago sights in a handful of days. But if you prefer to discover hidden spots or go on day tours, consider booking your New Chicago vacation for longer.
How to find the best New Chicago package deals?
Begin your search for a New Chicago package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect New Chicago package deal right away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your New Chicago adventure off to a flying start.
Is it cheaper to book a New Chicago vacation as a package?
You can enjoy significant savings on your New Chicago escape by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to view some great airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to New Chicago?
If you're considering 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 score amazing deals on your hotels and flights by booking ahead.
How to plan a trip to New Chicago?

  1. Choose the ideal time to travel: Your schedule, favorite season and the type of weather you enjoy can all influence your decision on when to travel to New Chicago.
  2. Work out your budget: Make sure you have enough money to pay for everything from dining out and transportation to experiences and flights. Your hotel will likely be the biggest expense during your trip to New Chicago.
  3. Determine how many days away: Start by compiling a list of the attractions you'd like to get to in New Chicago. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights 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.