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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,256, price is now CA $833 per person
CA $833
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,797 reviews)
The room, the location, the amenities it comes with it’s fair for the price

Reviewed on Jun 30, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,665, price is now CA $1,113 per person
CA $1,113
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,128 reviews)
Muriel at the front desk made our 54th Anniversary memorable as she upgraded our room to a suite and sent a bottle of Prosecco and box of chocolates to our room plus a voucher for oysters at the restaurant. Kudos to her for being so kind and thoughtful. Thank you so much!!

Reviewed on Jun 30, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,424, price is now CA $990 per person
CA $990
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
Very clean, great location. Every staff member we encountered was just terrific

Reviewed on Jun 30, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,635, price is now CA $1,143 per person
CA $1,143
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,330 reviews)
Nice clean room with minimalist/industrial vibe. Room was spacious. The front desk was helpful. The coffee shop was much appreciated.

Reviewed on Jun 30, 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 CA $1,765, price is now CA $1,243 per person
CA $1,243
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Great stay; fabulous location, amazing views and access to so much; friendly staff. Super friendly and accommodating housekeeping! Food/bar service took a long long time, every time..long wait to order…long wait to get drinks…long wait to pay bill. Not enough staff behind the bar.

Reviewed on Jun 30, 2026

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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 $166 per night from Jul 7 to Jul 8
CA $166
CA $203 total
Jul 7 - Jul 8
includes taxes & fees
8.6/10 Excellent! (1,047 reviews)
"Clean room, very quiet and comfortable."

Reviewed on Jun 28, 2026

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 $105 per night from Jul 14 to Jul 15
CA $105
CA $119 total
Jul 14 - Jul 15
includes taxes & fees
4.6/10 (1,003 reviews)
"She ores are near by! Most are walking distance!"

Reviewed on Jun 28, 2026

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 $129 per night from Jul 12 to Jul 13
CA $129
CA $145 total
Jul 12 - Jul 13
includes taxes & fees
7.2/10 Good! (357 reviews)
"Your Continental breakfast needs to improve it could have been better"

Reviewed on Jun 30, 2026

Days Inn and Suites by Wyndham Hammond, IN
See all 517 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 $833 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.

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.