Winfield Holidays from AU$2,499

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Your Winfield Holiday

When you organise a holiday package to Winfield, you can relax and enjoy your escape knowing your travel plans have been worked out ahead of time. Uncover the wonders of this lively city while based in a neighbourhood like Medinah, which is good for golfing. Fill your itinerary with visits to Wheaton College, College of Dupage and North Central College Fine & Performing Arts, some of the things you just have to see during your trip to Winfield. Whatever your travel plans or budget, putting together a tailored Winfield holiday is a piece of cake with Expedia.

The Latest Winfield Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was AU$2,874, price is now AU$2,499 per person
AU$2,499
per person
2 Sept - 5 Sept
found 1 day ago
Return direct flight included
Brisbane (BNE) to Chicago (ORD)
8.2/10 Very good! (2,854 reviews)
We really enjoyed our stay. clean rooms and staff was very friendly

Reviewed on 22 July 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was AU$3,374, price is now AU$2,723 per person
AU$2,723
per person
2 Sept - 5 Sept
found 1 day ago
Return direct flight included
Brisbane (BNE) to Chicago (ORD)
9.4/10 Exceptional! (4,714 reviews)
Great location and clean room.

Reviewed on 23 July 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was AU$3,445, price is now AU$2,787 per person
AU$2,787
per person
2 Sept - 5 Sept
found 1 day ago
Return direct flight included
Brisbane (BNE) to Chicago (ORD)
9.2/10 Wonderful! (1,150 reviews)

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was AU$3,307, price is now AU$2,772 per person
AU$2,772
per person
2 Sept - 5 Sept
found 1 day ago
Return direct flight included
Brisbane (BNE) to Chicago (ORD)
9.2/10 Wonderful! (1,035 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was AU$3,810, price is now AU$3,251 per person
AU$3,251
per person
2 Sept - 5 Sept
found 1 day ago
Return direct flight included
Brisbane (BNE) to Chicago (ORD)
9.6/10 Exceptional! (1,934 reviews)

Winfield Holiday

Winfield Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
9,700
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Arcada Theatre, Paramount Theatre and DuPage Childrens Museum

Our pick of the best 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 AU$308 per night from 6 Aug to 7 Aug
AU$308
6 Aug - 7 Aug
includes taxes & fees
8.8/10 Excellent! (2,880 reviews)
"The hotel advertises a swimming pool and when we asked where we could find it that’s when they told us there is no pool. Apparently there has not been a pool in years. Another issue was the room we were given was nothing like the one in the photos. Not happy at all with their false advertising. Lastly ..."

Reviewed on 23 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 AU$408 per night from 7 Aug to 8 Aug
AU$408
7 Aug - 8 Aug
includes taxes & fees
8.4/10 Very good! (2,364 reviews)
"Everything was great"

Reviewed on 22 July 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 AU$174 per night from 9 Aug to 10 Aug
AU$174
9 Aug - 10 Aug
includes taxes & fees
8/10 Very good! (3,090 reviews)
"Bed was broken I told them they didn’t help me with that and didn’t provide me any other room"

Reviewed on 23 July 2026

Comfort Suites Chicago O'Hare Airport
See all 1,337 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.
All Inclusive Holidays
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All Inclusive Holidays
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beach holidays
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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

AU$39
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

AU$58
per adult
92% of travellers recommend
Art Institute of Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$59
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Winfield

Frequently asked questions

How much does a Winfield holiday package cost?
You'll find cheap prices from AU$2,499 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.

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