Winfield Vacations from ￥317,022

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The Latest Winfield Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

3 out of 5
Price was ￥356,392, price is now ￥317,022 per person
￥317,022
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,073 reviews)
If going to Allstate for any reason best affordable stay

Reviewed on Oct 26, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥518,514, price is now ￥456,260 per person
￥456,260
per person
Jan 3 - Jan 9
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)

Hilton Rosemont Chicago O'Hare

Hilton Rosemont Chicago O'Hare

3.5 out of 5
Price was ￥462,301, price is now ￥407,801 per person
￥407,801
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
Loved this hotel and will stay again.

Reviewed on Oct 26, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was ￥515,734, price is now ￥459,628 per person
￥459,628
per person
Jan 3 - Jan 9
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
This place is great and clean

Reviewed on Oct 26, 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was ￥552,384, price is now ￥494,025 per person
￥494,025
per person
Jan 3 - Jan 9
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
Wonderful stay, super clean and staff was verybhelpful

Reviewed on Oct 26, 2026

Find the Best Winfield Vacation Packages

Winfield Hotel Deals

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥33,202 per night from Nov 22 to Nov 23
￥33,202
￥38,975 total
Nov 22 - Nov 23
includes taxes & fees
Hilton Chicago O'Hare Airport
Chicago Club Inn & Suites

Chicago Club Inn & Suites

3 out of 5
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
The price is ￥10,667 per night from Nov 2 to Nov 3
￥10,667
￥11,838 total
Nov 2 - Nov 3
includes taxes & fees
7.2/10 Good! (1,890 reviews)
"The property itself is very rundown not modern at all. When you enter the property, it smelled like marijuana. There were tons of supplies everywhere almost as if a renovation was going to happen. No one ever checked to see if we needed additional towels, the lighting in the room was horrible. There ..."

Reviewed on Oct 26, 2026

Chicago Club Inn & Suites
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road Chicago IL
The price is ￥22,448 per night from Nov 25 to Nov 26
￥22,448
￥26,352 total
Nov 25 - Nov 26
includes taxes & fees
8.6/10 Excellent! (1,449 reviews)
"No microwave in the rroom. The temperature of the room wouldn’t Go below 65 but the hallway were cold. bathroom to small"

Reviewed on Oct 26, 2026

Marriott Chicago O'Hare
See all 1,376 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.

Stay near popular Winfield attractions

Royal Golf Club at Klein Creek

This challenging 18-hole championship course features rolling prairieland and strategic water hazards. Enjoy the cozy clubhouse and Americana cuisine after tackling the notorious 9th hole, one of Chicago's toughest par 4s.
See properties

What to do in Winfield

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥3,812
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

￥6,275
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

￥6,642
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
See all activities in Winfield

Frequently asked questions

How much does a Winfield vacation package cost?
You'll find cheap prices from ￥317,022 on Expedia for your Winfield getaway. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Winfield costs.
What are the cheapest months to go to Winfield?
Travel in the off-season and you're likely to find cheap Winfield vacation packages. Bear in mind that public holidays and local events and festivals can impact prices, so do a little research before booking.
How many days is enough for Winfield?
The ideal length for your Winfield vacation depends on what you'd like to see. Usually, a few days to a week will give you time to hit all the main attractions and explore some hidden treasures along the way.
How to find the best Winfield package deals?
Start your search for a Winfield package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Winfield package deal straight away, just play around with your dates and search again. Remember 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 break by booking a tailored vacation package. Check the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Winfield?
Score amazing discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Winfield break.
How to plan a trip to Winfield?

  1. Choose the right 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 like flights, transportation and food when working out how much to set aside for your trip to Winfield. Then, select a property that suits your budget, whether that's an economical stay or a high-end retreat.
  3. Determine how many days away: Start by making a list of all the attractions you'd like to experience in Winfield. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to pick 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.