Winfield Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,691, price is now CA $1,132 per person
CA $1,132
per person
Jun 20 - Jun 23
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Very quiet, really clean and staff was great
Reviewed on Apr 2, 2026
Hotel Chicago Downtown, Autograph Collection by Marriott
Downtown Chicago
Price was CA $1,944, price is now CA $1,327 per person
CA $1,327
per person
May 5 - May 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
Nice hotel with friendly staff! Housekeeping very helpful and kind. It does seem the front desk was understaffed for the size of hotel and how busy it was. Was hard to get call answered when phoned desk.
Reviewed on Mar 30, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,617, price is now CA $1,176 per person
CA $1,176
per person
May 7 - May 11
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Hotel is in a good central location near many of the main attractions. Room was spacious and clean. Nice bar downstairs, there is also a rooftop bar, but that is only open in after Easter in summer.
Buffet breakfast is included and that makes it very good value. Hotel also has a gym/
Not too many amenities in the room though.
Reviewed on Apr 2, 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 $72 per night from Apr 5 to Apr 6
CA $72
CA $81 total
Apr 5 - Apr 6
includes taxes & fees
6.4/10 (1,001 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 $62 per night from Apr 3 to Apr 4
CA $62
CA $70 total
Apr 3 - Apr 4
includes taxes & fees
7/10 Good! (576 reviews)
Definitely needs some updates (which looks like are being slowly done). But a quiet place close to food
Reviewed on Apr 1, 2026
Hampton Inn & Suites Munster
8936 Calumet Ave Munster IN
Fully refundableReserve now, pay when you stay
The price is CA $170 per night from Apr 26 to Apr 27
CA $170
CA $190 total
Apr 26 - Apr 27
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Excellent
Reviewed on Mar 27, 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.
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.
