New Chicago Vacations from ￥551,993
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest New Chicago Vacation Packages
Price found within the past 48 hours. Click for updated prices.
AC Hotels by Marriott Chicago Downtown
Downtown Chicago
￥554,988
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.8/10 Excellent! (1,009 reviews)
My family and I had a wonderful stay. The staff were awesome and the location is excellent. Rooms clean and comfortable. Chris the bell hop made our time there even more enjoyable. We are already planning our return trip!
Reviewed on Sep 12, 2026
Find the Best New Chicago Vacation Packages
New Chicago Hotel Deals
Ameristar Casino Hotel East Chicago
777 Ameristar Blvd. East Chicago IN
Fully refundableReserve now, pay when you stay
￥22,272
￥26,786 total
Oct 5 - Oct 6
includes taxes & fees
Motel 6 Hammond, IN - Chicago Area
3840 179th St Hammond IN
Fully refundableReserve now, pay when you stay
￥9,215
￥10,631 total
Sep 20 - Sep 21
includes taxes & fees
Fairfield Inn and Suites By Marriott Merrillville
8275 Georgia St Merrillville IN
Fully refundableReserve now, pay when you stay
￥13,207
￥14,792 total
Oct 4 - Oct 5
includes taxes & fees
7.8/10 Good! (1,002 reviews)
"Expedia is terrible!!! When I arrived at my hotel after a 3-hour drive. I discovered my room had been sold. The front desk person told me that they had sent an email for the cancellation. She then directed me back to the third-party booking agent (Expedia) for a refund. I actually received the cancelation ..."
Reviewed on Sep 12, 2026
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 ￥551,993 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?
- 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.
- 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.
- 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.
- 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.
