Winfield Holidays from £669

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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 many charms of this amazing city from your base in a neighbourhood like Medinah, which is great for golfing. Fill your itinerary with tours of Wheaton College, College of Dupage and North Central College Fine & Performing Arts, some of the attractions you just have to see during a trip to Winfield. Expedia has what you need to escape your daily routine. Tailor your holiday to Winfield to suit your travel style, whatever that may be!

Top Winfield Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,050, price is now £669 per person
£669
per person
6 Nov - 10 Nov
found 16 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
Rooms are basic and bathrooms and sink area small. But all comfortable

Reviewed on 17 Aug 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,724, price is now £1,037 per person
£1,037
per person
20 Sept - 27 Sept
found 19 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,033 reviews)
Loved the atmosphere and friendly atmosphere

Reviewed on 18 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,385, price is now £839 per person
£839
per person
6 Nov - 10 Nov
found 16 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,576, price is now £982 per person
£982
per person
20 Sept - 27 Sept
found 19 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,359 reviews)
The rooftop should be guest only or have a better security as some people skip to other floors with no cards and be a security threat

Reviewed on 18 Aug 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,266, price is now £807 per person
£807
per person
20 Sept - 27 Sept
found 19 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Great area: able to walk to many restaurants.

Reviewed on 18 Aug 2025

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 Lynfred Winery

Top hotels in Winfield

Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £117 per night from 6 Sept to 7 Sept
£117
6 Sept - 7 Sept
includes taxes & fees
8.4/10 Very Good! (1,125 reviews)
"."

Reviewed on 16 Aug 2025

Marriott Chicago O'Hare
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 £155 per night from 12 Sept to 13 Sept
£155
12 Sept - 13 Sept
includes taxes & fees
8.2/10 Very Good! (2,088 reviews)
"Very convenient for early/late flights, room clean, overall quiet, bed was pretty soft/low to the ground, service a little slow."

Reviewed on 12 Aug 2025

Hilton Chicago O'Hare Airport
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
5440 N River Rd, Rosemont, IL
Fully refundable
The price is £104 per night from 1 Sept to 2 Sept
£104
1 Sept - 2 Sept
includes taxes & fees
8.6/10 Excellent! (2,399 reviews)
"Close to ORD airport. Very clean hotel and rooms. Water pressure really good and hot!"

Reviewed on 18 Aug 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
See all 1,301 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
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North which includes street scenes, signage and night scenes

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier

Navy Pier

4/5(125 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Winfield

River tour boat in Chicago

Architecture River Tour

£31
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Winfield

Frequently asked questions

Why should I book my Winfield holiday with Expedia?
Expedia has you covered for all aspects of your upcoming Winfield getaway. You'll always land the best prices, but when you bundle your flights, hotel and/or car hire into a holiday package, you'll score even bigger savings. Keen to truly make the most of your adventure? Add a few fun activities and tours to your package. Expedia offers flexible cancellation policies on almost all bookings, so there's no need to worry if your plans change. Head over to our Customer Service Portal link to learn more.
When is the best time of year to holiday in Winfield?
If you love the excitement that comes with peak season, visit Winfield in March, May and June. If you're looking for a calmer vibe, December, January and February will suit you better. Plan your getaway to Winfield based on what kind of adventure you want. January is the coolest time of year, when daytime temperatures average -4ºC. In July, the warmest period, you will experience temperatures of around 23ºC during the day.
What is the top hotel for my holiday in Winfield?
LondonHouse Chicago, Curio Collection by Hilton is a perfect base for a wonderful trip to Winfield, offering all the comforts and amenities you need and more.
How do I get a cheap holiday to Winfield?
Browse and lock in everything in one place with our Winfield holidays. You'll find deals on hotels, flights and more that'll keep your credit card happy and your adventurous spirit busy. And, with more than 400 air carriers and 321,000 hotels across the globe to select from, you'll have endless opportunities to mix and match all you want. Learn more about how you can save money on your holiday when you book a flight and hotel together with Expedia.
What should I do on my Winfield holiday?
Make sure your holiday in Winfield is an unforgettable one by checking out its leading attractions. Chicago Premium Outlets, Arcada Theatre, Morton Arboretum and Wheaton College are just a few of the things you must see while you're in this city.
What is the best area to stay in when on holiday in Winfield?
If you're interested in visiting Royal Golf Club at Klein Creek, save yourself the hassle of commuting and book a stay close by. It's one of the top attractions in Winfield.
Do I need a visa for my Winfield holiday?
Visa requirements for Winfield vary based on your nationality and the purpose of your visit. Be sure to check official government websites to determine if you need a visa for your trip. They'll give you the most up-to-date information, including details about application procedures and any supporting documentation you might need. Research your visa requirements well in advance to ensure a smooth travel experience. Also double-check to see that your passport has at least six months validity from the date of your return.
What should I wear on my Winfield holiday?
Though everyone's fashion style varies, it can be useful to have some guidelines for what to bring on your holiday in Winfield. We recommend looking up social media before you go for inspiration on local dress codes or fashion trends. Have a look at the weather forecast so you can pack accordingly. The warmest time of year in Winfield is July, with average daytime temperatures of 23ºC. If you plan to visit during the coolest month of January, the mercury hovers around -4ºC during the day.
What does an Expedia Winfield holiday include?
Much of that depends on you. Simply select from a variety of Winfield packages, such as a hire car, hotel and flight. You can also book a hotel with a flight, or a car hire with a flight. Once you've made your booking, add on the fun stuff like experiences and tours. Whatever your dream Winfield holiday looks like, get set to save! Check if there are any available private holiday homes in Winfield as they are the most popular property type here. You can also find other stays on Expedia and tailor your own unique travel experience.
Does Expedia offer Book Now, Pay Later Winfield holidays?
We do. Expedia has partnered with online lender Klarna to help you conveniently pay for your holiday in manageable instalments. Simply select the payment plan that suits best during checkout and take the stress out of budgeting for your next trip. Don't forget to bundle your flights, accommodation and car hire with Expedia to get the biggest bang for your travel buck. Consider these flexible payment options below:

  • Pay monthly holidays: Jet off on that dream holiday sooner with Klarna's convenient monthly instalment plans. If paying in multiple transactions sounds right for you, pick this option at checkout.
  • No-deposit holidays: Pressing the "book now" button is much easier with this option. With no upfront fee for your holiday, you can Book Now, Pay Later and start working on your travel itinerary.

Can I choose my airline with a Winfield Expedia holiday?
Yes — that's the beauty of an Expedia holiday package. You get to choose. We have access to more than 400 airline partners all over the world, so you have loads of choice when putting together your Winfield adventure.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.