Winfield Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ฿27,000 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

Top hotels in Winfield

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 ฿6,355 per night from 6 Aug to 7 Aug
฿6,355
฿7,244 total
6 Aug - 7 Aug
includes taxes & fees
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 ฿9,382 per night from 7 Aug to 8 Aug
฿9,382
฿11,013 total
7 Aug - 8 Aug
includes taxes & fees
8.4/10 Very good! (2,346 reviews)
"On the airport property very easy to get to my flight in the morning"

Reviewed on 18 Jul 2026

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 ฿3,665 per night from 19 Jul to 20 Jul
฿3,665
฿4,214 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 cosy 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

฿904
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago CityPASS: Admission to Top 5 Chicago Attractions

Chicago CityPASS®: Experience 5 must-see attractions

฿4,820
per adult
94% of travellers recommend
Chicago CityPASS®: Experience 5 must-see attractions
Art Institute of Chicago

Art Institute of Chicago

฿1,339
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Winfield

Frequently asked questions

How much does a Winfield holiday package cost?
You'll find cheap prices on Expedia for your Winfield getaway. However, factors like the season, choice of hotel and length of stay will determine how much your holiday 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 holiday 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 holiday 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 holiday as a package?
You can enjoy significant savings on your next Winfield break by booking a tailored holiday package. Check the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday 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 holiday package that brings all your bookings together.

Explore a world of travel with Expedia

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