Winfield Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Winfield Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$989, price is now S$696 per person
S$696
per person
17 Oct - 20 Oct
found 1 day ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
8.4/10 Very Good! (1,450 reviews)
I think this is a good hotel in an extremely convenient location whether you plan to walk or catch a ride. Close to everything and staff was pleasant.

Reviewed on 19 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 S$1,791, price is now S$1,134 per person
S$1,134
per person
17 Oct - 20 Oct
found 1 day ago
Return direct flight included
Fort Lauderdale (FLL) 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

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$2,043, price is now S$1,388 per person
S$1,388
per person
17 Oct - 20 Oct
found 1 day ago
Return direct flight included
Fort Lauderdale (FLL) 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

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,206, price is now S$848 per person
S$848
per person
17 Oct - 20 Oct
found 1 day ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
Loved the atmosphere and friendly atmosphere

Reviewed on 18 Aug, 2025

L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,382, price is now S$984 per person
S$984
per person
17 Oct - 20 Oct
found 1 day ago
Return direct flight included
Fort Lauderdale (FLL) to Chicago (ORD)
9.6/10 Exceptional! (2,837 reviews)
Property was well located to be able to explore Chicago easily. Very clean hotel and the staff was extremely accommodating. The only thing missing was a pool but it wasn’t a huge issue. Very nice hotel and would go back for sure.

Reviewed on 20 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 S$161 per night from 1 Sept to 2 Sept
S$161
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 S$107 per night from 24 Aug to 25 Aug
S$107
24 Aug - 25 Aug
includes taxes & fees
4.2/10 (1,000 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 S$131 per night from 25 Aug to 26 Aug
S$131
25 Aug - 26 Aug
includes taxes & fees
6.6/10 (73 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 S$696 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.