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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 8 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
Bad room service, bad dinner/breakfast service at the restaurants and no house keeping - had to ask for it - and when they finally did they didn’t restock the bar or towels.

Reviewed on Aug. 4, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
Sep 8 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on Jul. 26, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Sep 8 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on Jul. 22, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
Sep 10 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,049 reviews)
Amazing view, nice room sizes and very clean

Reviewed on Aug. 3, 2025

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
per person
Oct 10 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (3,055 reviews)
Had a lovely stay during the weekend and would likely stay here again in the near future. Staff always greeted me when leaving or entering the building every day and wished me well.

Reviewed on Aug. 4, 2025

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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 20 to Aug 21
CA $121
CA $150 total
Aug 20 - Aug 21
includes taxes & fees
8.4/10 Very Good! (1,012 reviews)
"Everything was good, but I requested housekeeping and no one never came besides that things was ok"

Reviewed on Aug. 4, 2025

Ameristar Casino Hotel East Chicago
Spring House Inn

Spring House Inn

2.5 out of 5
303 N Mineral Springs Rd, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Sep 2 to Sep 3
CA $150
CA $175 total
Sep 2 - Sep 3
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"We enjoyed staying at the Spring House Inn! The room was clean and spacious. There were great options at the continental breakfast. The staff was friendly & helpful! Our stay was great!"

Reviewed on Jul. 30, 2025

Spring House Inn
Best Western Indian Oak

Best Western Indian Oak

2.5 out of 5
558 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from Sep 1 to Sep 2
CA $140
CA $157 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very Good! (1,013 reviews)
"Scary raccoons"

Reviewed on Aug. 3, 2025

Best Western Indian Oak
See all 453 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
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Winfield vacation package cost?
Offering great value package deals from CA $1,189 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.