New Chicago Vacations from ￥308,218

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The Latest New Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Oct 17 - Oct 24
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
The hotel is beautiful inside and out and the staff are super nice and helpful. Hotel is in a very crowded area. It can take time to get in and out with your car. A lot of noise from the outside even when staying on top floors. Hotel could be managed better. Elevator was broken for a whole day. Room had some minor repairs that were not done when we checked in.

Reviewed on Jul 28, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Oct 10 - Oct 17
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (324 reviews)
I liked the hotel room's kitchen and it is very nice, however VERY small. The pool/amenities are also very nice. One major challenge was there was a last minute change to the location of our reservation from old town to fulton market. They did communicate the change and provided a discount, however, this occurred the day before our trip. The check-in process was also very disorganized and confusing. Information easily accessible in the reservation was not used, requiring extra check-in time. They told us a crib was available, and later found only a pack and play. I requested bedding for the pull out 4 times before someone brought them. Overall, management needs to improve their operations.

Reviewed on Jul 21, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 10 - Oct 17
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on Jul 26, 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
per person
Oct 17 - Oct 24
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Very nice location super friendly staff very modern and clear hotel

Reviewed on Jul 27, 2025

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
per person
Oct 10 - Oct 17
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,042 reviews)
Beautiful Hotel! Rooftop pool is wonderful!

Reviewed on Jul 27, 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 ￥16,303 per night from Jul 29 to Jul 30
￥16,303
￥19,735 total
Jul 29 - Jul 30
includes taxes & fees
8.4/10 Very Good! (1,029 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 4 to Aug 5
￥19,052
￥21,338 total
Aug 4 - Aug 5
includes taxes & fees
8.8/10 Excellent! (1,018 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 ￥11,300 per night from Aug 3 to Aug 4
￥11,300
￥12,766 total
Aug 3 - Aug 4
includes taxes & fees
7.4/10 Good! (1,029 reviews)
"We loved the pillows! Overall, we had a very nice stay. No complaints."

Reviewed on Jul 25, 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 ￥308,218 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.