Winfield Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Winfield Vacation Packages

Winfield Hotel Deals

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is SARĀ 635 per night from Aug 3 to Aug 4
SARĀ 635
SARĀ 723 total
3 Aug - 4 Aug
includes taxes & fees
8.8/10 Excellent! (2,840 reviews)
"Everything was good"

Reviewed on 17 July 2026

Hyatt Regency O'Hare Chicago
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 SARĀ 1,048 per night from Aug 7 to Aug 8
SARĀ 1,048
SARĀ 1,230 total
7 Aug - 8 Aug
includes taxes & fees
Hilton Chicago O'Hare Airport
Comfort Suites Chicago O'Hare Airport

Comfort Suites Chicago O'Hare Airport

3 out of 5
4200 North River Road Schiller Park IL
Fully refundable
The price is SARĀ 409 per night from Jul 19 to Jul 20
SARĀ 409
SARĀ 471 total
19 Jul - 20 Jul
includes taxes & fees
Comfort Suites Chicago O'Hare Airport
See all 1,341 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.
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Frequently asked questions

How much does a Winfield vacation package cost?
You'll find cheap prices on Expedia for your Winfield getaway. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Winfield costs.
What are the cheapest months to go to Winfield?
The off-season is the best time to head to Winfield if you're trying to save. Another tip for scoring cheap Winfield vacation packages? Avoid visiting during public holidays and any major events.
How to find the best Winfield package deals?
Use Expedia's filter tool to help you find some tempting Winfield package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for Winfield package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Winfield vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging stays and flights separately. Better still, you can tailor your Winfield escape to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Winfield?
Secure fantastic discounts by booking your flights in advance with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Winfield break.
How to plan a trip to Winfield?

  1. Choose when to travel: Check your diary and pack your bags. Your preferred season and the type of activities on offer will also help you decide when to vacation in Winfield.
  2. Set a budget: Consider costs such as flights, transportation and food when working out how much to set aside for your trip to Winfield. Then, select a property that fits your budget, whether that's an economical stay or a more upscale getaway.
  3. Decide how many days away: Start by listing all the sights and activities you want to experience in Winfield. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to pick a Winfield vacation package that brings all your bookings together.