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.
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination
Price was CA $890, price is now CA $617 per person
CA $617
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (998 reviews)
I enjoyed my stay here. Clean and friendly environment
Reviewed on Apr 4, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,815, price is now CA $1,156 per person
CA $1,156
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Beautiful rooms at an amazing location. Parking is terribly expensive though, and breakfast is not included. There is no mini fridge, so good luck saving leftovers to reduce expenses. There is also no swimming pool which I found weird for a place this elegant.
Their main restaurant does not have good breakfast. Go for dinner or lunch and you will be very happy. But don't bother with breakfast, it's just a bunch of cheese and grease and it's unpleasant.
Reviewed on Apr 4, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,432, price is now CA $1,041 per person
CA $1,041
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
Was a little noisy but I think that was just my unit. Facilities were top notch!
Reviewed on Apr 4, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,493, price is now CA $1,117 per person
CA $1,117
per person
Jun 5 - Jun 7
found 6 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
Best free Hotel breakfast you will ever have
Reviewed on Apr 4, 2026
Hotel 55 Chicago Downtown
Downtown Chicago
Price was CA $1,436, price is now CA $1,076 per person
CA $1,076
per person
May 14 - May 17
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,575 reviews)
The room was spacious and the decor was lovely. It was conveniently located right next to Marshalls, making it easy to grab a quick snack or a new pair of shoes. The hotel is also just a 10-minute walk from the riverfront, where you can enjoy a leisurely stroll or take a boat ride. From there, it’s only a 5-6 minute walk to the Bean, a popular coffee shop that’s perfect for a quick caffeine fix. And if you’re looking for some shopping, the Starbucks Reserve is just a 2-minute walk away. Overall, this hotel offers a great combination of convenience and amenities, making it a perfect choice for any traveler.
Reviewed on Apr 4, 2026
Winfield Hotel Deals
Motel 6 Hammond, IN - Chicago Area
3840 179th St Hammond IN
Fully refundableReserve now, pay when you stay
The price is CA $73 per night from Apr 6 to Apr 7
CA $73
CA $81 total
Apr 6 - Apr 7
includes taxes & fees
6.4/10 (1,003 reviews)
My hotel room smelled like cigarette smoke. Even though it was about 90% clean, there were a few details that could be considered dirty. Within the entire complex, the hotel is practically at the very end—far away from everything. If you’re looking for a place near shops or restaurants, this isn’t ...
Reviewed on Apr 1, 2026
FairBridge Inn Express Merrillville
8250 Louisiana Street Merrillville IN
Fully refundableReserve now, pay when you stay
The price is CA $63 per night from Apr 6 to Apr 7
CA $63
CA $70 total
Apr 6 - Apr 7
includes taxes & fees
7/10 Good! (580 reviews)
Great location, helpful staff, budget room
Reviewed on Apr 3, 2026
Hampton Inn & Suites Munster
8936 Calumet Ave Munster IN
Fully refundableReserve now, pay when you stay
The price is CA $160 per night from Apr 19 to Apr 20
CA $160
CA $179 total
Apr 19 - Apr 20
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
Breakfast was good. Staff was helpful and nice. Pool was cold but hot tub was hot.
Reviewed on Apr 3, 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
