Winfield Vacations from ￥231,194

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The Latest Winfield Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
per person
Sep 18 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,011 reviews)
Great staff and services!

Reviewed on Jul 23, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Sep 18 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Close proximity to everything

Reviewed on Jul 22, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 12 - Oct 17
found 23 hours 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

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
per person
Sep 18 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,484 reviews)
Very nice and clean place

Reviewed on Jul 21, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
Sep 13 - Sep 17
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Beautiful, welcoming, quiet, lovely linens and bed

Reviewed on Jul 20, 2025

Find the Best Winfield Vacation Packages

Winfield 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 Jul 28 to Jul 29
￥16,589
￥20,049 total
Jul 28 - Jul 29
includes taxes & fees
8.4/10 Very Good! (1,015 reviews)
"My husband and I enjoyed our stay in the hotel. The king room was very spacious which we really appreciated. It was clean and the bed was comfortable. We enjoyed the casino but did not utilize any of the other amenities to say about the food."

Reviewed on Jul 19, 2025

Ameristar Casino Hotel East Chicago
Spring House Inn

Spring House Inn

2.5 out of 5
303 N Mineral Springs Rd, Chesterton, IN
The price is ￥18,892 per night from Aug 3 to Aug 4
￥18,892
￥21,159 total
Aug 3 - Aug 4
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
Best Western Indian Oak

Best Western Indian Oak

2.5 out of 5
558 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is ￥16,250 per night from Aug 13 to Aug 14
￥16,250
￥18,201 total
Aug 13 - Aug 14
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
"I liked the small lake by the breakfast dining area and the hotel was very clean and staff was wonderful."

Reviewed on Jul 16, 2025

Best Western Indian Oak
See all 464 properties in Winfield
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 Winfield vacation package cost?
Offering great value package deals from ￥231,194 on Expedia, you'll be thrilled with how little a vacation to Winfield costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Winfield?
You're likely to find reduced prices and greater availability in January, February and March. Take a look at our cheap Winfield vacation packages and you could get some excellent off-season deals.
How many days is enough for Winfield?
With a well-planned itinerary, you can easily visit the top Winfield attractions in a few days. But if you want to discover hidden spots or go on day trips, think about booking your Winfield vacation for longer.
How to find the best Winfield package deals?
Begin your search for a Winfield package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Winfield package deal right away, simply switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Winfield adventure underway.
Is it cheaper to book a Winfield vacation as a package?
You can enjoy significant savings on your next Winfield retreat by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to view the best hotel prices and airfares. Bundle everything into a great-value 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 Winfield?
If you're planning a spontaneous Winfield getaway, 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 find terrific deals on your hotels and flights by booking ahead.
How to plan a trip to Winfield?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Winfield.
  2. Set a budget: Factor in costs such as food, flights and transportation when calculating how much to set aside for your trip to Winfield. Then, pick a property that fits your budget, whether that's a wallet-friendly stay or a lavish retreat.
  3. Decide how long to go for: Now that you know more about Winfield, you can work out the right length of your break. Put together a rough plan and allocate enough time to get through everything on your must-do list.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose a Winfield vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.