Winfield Holidays

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Top Flight + Hotel Deals in Winfield

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was €946, price is now €630 per person
€630
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Everyone was wonderful and the property and rooms are very well maintained. Will definitely stay there again.

Reviewed on 24 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €1,932, price is now €1,162 per person
€1,162
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was €1,430, price is now €872 per person
€872
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on 22 Aug 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was €1,979, price is now €1,240 per person
€1,240
per person
2 Nov - 7 Nov
found 7 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was €1,206, price is now €796 per person
€796
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Everything was nice!!

Reviewed on 23 Aug 2025

Top hotels in Winfield

Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

4 out of 5
777 Ameristar Blvd., East Chicago, IN
Fully refundableReserve now, pay when you stay
The price is €112 per night from 1 Sept to 2 Sept
€112
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
"The Ameristar Casino Hotel East Chicago absolutely exceeded my expectations! The room was honestly one of the best I’ve ever stayed in — incredibly spacious, spotless, and so comfortable that it felt like a luxury retreat. I went during an off-season day, so the price was very affordable, which made ..."

Reviewed on 19 Aug 2025

Ameristar Casino Hotel East Chicago
Red Roof Inn Chicago - Lansing

Red Roof Inn Chicago - Lansing

2 out of 5
2450 East 173rd Street, Lansing, IL
Fully refundableReserve now, pay when you stay
The price is €71 per night from 25 Aug to 26 Aug
€71
25 Aug - 26 Aug
includes taxes & fees
4.2/10 (1,002 reviews)
"It’s a cool little spot. If you have a pet, you could bring your pet no drama not too much noise."

Reviewed on 7 Aug 2025

Red Roof Inn Chicago - Lansing
Days Inn and Suites by Wyndham Hammond, IN

Days Inn and Suites by Wyndham Hammond, IN

2 out of 5
4000 Calumet Avenue, Hammond, IN
Fully refundableReserve now, pay when you stay
The price is €88 per night from 25 Aug to 26 Aug
€88
25 Aug - 26 Aug
includes taxes & fees
6.6/10 (72 reviews)
"Recently remodeled and nice"

Reviewed on 21 Aug 2025

Days Inn and Suites by Wyndham Hammond, IN
See all 458 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.

Frequently asked questions

How much does a Winfield holiday package cost?
Offering great value package deals from €630 on Expedia, you'll be thrilled with how little a holiday to Winfield costs! Expedia's packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Winfield?
You're likely to find reduced prices and greater availability in January, February and March. Take a look at our cheap Winfield holiday packages and you could get some excellent off-season deals.
How many days is enough for Winfield?
With a well-planned itinerary, you can easily visit the top Winfield attractions in a few days. But if you want to discover hidden spots or go on day trips, think about booking your Winfield holiday for longer.
How to find the best Winfield package deals?
Begin your search for a Winfield package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Winfield package deal right away, simply switch up your dates and search again. Bear in mind 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 retreat by booking a personalised holiday package. Click on the "Package" heading, then select your travel dates and destination to view the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Winfield?
If you're planning a spontaneous Winfield getaway, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find terrific deals on your hotels and flights by booking ahead.
How to plan a trip to Winfield?

  1. Pick the ideal 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 such as food, flights and transportation when calculating how much to set aside for your trip to Winfield. Then, pick a property that fits your budget, whether that's a wallet-friendly stay or a lavish retreat.
  3. Decide how long to go for: Now that you know more about Winfield, you can work out the right length of your break. Put together a rough plan and allocate enough time to get through everything on your must-do list.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose 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.