Winfield Vacation Packages

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Your Winfield Vacation

Our vacation packages to Winfield provide endless opportunities to discover new sights, sounds and experiences. And with all the planning worked out, you can breathe easy and enjoy your city getaway without a worry in the world. Love to explore your new surroundings? Deep River Water Park, Crown Point Sports Complex and Lake County Fairgrounds are some of the leading places to visit during your trip to Winfield. A couple of clicks is all it takes to craft a tailor-made Winfield vacation on Expedia.

Top Winfield Vacation Deals

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 CA $1,018, price is now CA $639 per person
CA $639
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Great Staff, Beautiful Hotel!

Reviewed on Aug. 22, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $3,441, price is now CA $1,974 per person
CA $1,974
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on Aug. 19, 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was CA $1,775, price is now CA $1,041 per person
CA $1,041
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (1,962 reviews)
Staff were excellent, I needed to mail some parcels for a business event which they held for over a week (arrived earlier than expected!) breakfast was also excellent. Rooms were noisy, not from outside but from the other rooms. Walls must be thin and could hear conversation and the TV from both sides.

Reviewed on Aug. 20, 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was CA $2,444, price is now CA $1,439 per person
CA $1,439
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.

Reviewed on Aug. 21, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $3,954, price is now CA $2,330 per person
CA $2,330
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug. 10, 2025

Ready to book your vacation to Winfield?

 

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Winfield Hotel Deals

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 CA $121 per night from Aug 25 to Aug 26
CA $121
CA $150 total
Aug 25 - Aug 26
includes taxes & fees
8.4/10 Very Good! (1,000 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 Aug. 19, 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 CA $103 per night from Aug 24 to Aug 25
CA $103
CA $116 total
Aug 24 - Aug 25
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 Aug. 7, 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 CA $130 per night from Aug 25 to Aug 26
CA $130
CA $146 total
Aug 25 - Aug 26
includes taxes & fees
6.4/10 (69 reviews)
A Great Stay!!
"My husband and I visit with Days Inn was very nice. Helpful and friendly Front Desk Staff, and friendly housekeeping staff. Their breakfast was nice! Nice clean hotel."

Reviewed on Aug. 20, 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.
All Inclusive Vacations
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Frequently asked questions

How much does a Winfield vacation package cost?
Offering great value package deals from CA $639 on Expedia, you'll be thrilled with how little a vacation to Winfield costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Winfield?
If you're hoping to book a cheap Winfield vacation package, consider travelling in January, February and March. You'll typically find better prices on flights and accommodations during these months — perfect for a budget-friendly break.
How many days is enough for Winfield?
With a well-organized schedule, you can easily tick off the most popular Winfield sights in a few days. But if you prefer to discover lesser-known spots or take day trips, think about booking your Winfield vacation for longer.
How to find the best Winfield package deals?
Landing a cheap Winfield package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget range, apply a few filters and browse what's available. You can personalize your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to view the most economical Winfield package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Winfield vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging flights and hotels individually. Better still, you can customize your Winfield escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Winfield?
If you've got your Winfield vacation dates confirmed, book as soon as you can to snap up some unbeatable deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to Winfield?

  1. Choose 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 your budget: Consider expenses like flights, food and transportation when calculating how much to put aside for your trip to Winfield. Then, choose a hotel that fits your budget, whether that's an affordable stay or a lavish retreat.
  3. Set the duration of your trip: Start by making a list of all the activities and attractions you want to experience in Winfield. Then, estimate how long you'll need for each, along with any travel time.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to pick a Winfield vacation 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.