Winfield Holidays from £1,001

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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.
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Price was £1,477, price is now £1,001 per person
£1,001
per person
21 Sept - 28 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (635 reviews)
I love the pool and exercise room access, breakfast was amazing

Reviewed on 1 Jul 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was £2,715, price is now £1,994 per person
£1,994
per person
22 Aug - 29 Aug
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
stay away, no one told us it had been damage and under repair, staff could not even help get me bording pass, room service sub par. We got a notice from Expedia after we checked in saying we could cancil, a bit to late.

Reviewed on 3 Jul 2026

Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was £1,522, price is now £1,125 per person
£1,125
per person
21 Sept - 28 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
Everything was lovely, but for reference the rooms with views on the first 5-6 floors are extremely noisy at night due to traffic etc.. Not the properties fault, although I would have thought there might be noise canceling glass or something like other hotels I've stayed at.

Reviewed on 30 Jun 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,637, price is now £1,236 per person
£1,236
per person
21 Sept - 28 Sept
found 24 hours ago
Return flight included
London (LON) to Chicago (ORD)
8.4/10 Very good! (2,006 reviews)
It was so amazing awesome.

Reviewed on 3 Jul 2026

Nobu Hotel Chicago

Nobu Hotel Chicago

5 out of 5
Downtown Chicago
Price was £1,670, price is now £1,295 per person
£1,295
per person
14 Aug - 18 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (873 reviews)
The staff was friendly and helpful. They let us check in early, and I got an upgraded room. Very nice property, I would stay here again.

Reviewed on 2 Jul 2026

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

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 £144 per night from 7 Jul to 8 Jul
£144
7 Jul - 8 Jul
includes taxes & fees
8.8/10 Excellent! (2,768 reviews)
"We were there under duress. Our flights had been canceled, our luggage delayed, and it was so late! The staff was amazing. They were quick and responsive. The room was gorgeous!! I set my alarm and slept late, and there were no disturbances. There was a wait for the restaurant to open. The atrium ..."

Reviewed on 3 Jul 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 £228 per night from 5 Jul to 6 Jul
£228
5 Jul - 6 Jul
includes taxes & fees
8.4/10 Very good! (2,318 reviews)
"Only thing I dont like is after a long haul flight I had to pull my luggage through their unbearable deep shaggy carpets. I was pulling 2 large bags through the lobby and to the room because they do not have porters to help you. That was brutal"

Reviewed on 3 Jul 2026

Hilton Chicago O'Hare Airport
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 £149 per night from 5 Jul to 6 Jul
£149
5 Jul - 6 Jul
includes taxes & fees
8.6/10 Excellent! (1,302 reviews)
"Nice pool, great desk staff. We only spent a night and didn't visit the bar or restaurant. Looked nice, but we had other plans. Lots of restaurants nearby. I'd book here again."

Reviewed on 3 Jul 2026

Marriott Chicago O'Hare
See all 1,329 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.
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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

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.

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. Flight-inclusive packages are ATOL protected.