Winfield Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
- Swissotel - Chicago
Jan 7 - Jan 11Swissotel - Chicago + Flight
Downtown Chicago4 nights4.5 star property9.0/10 - Wonderful (3,566 reviews)"Breakfast was good"Reviewed November 4, 2026Roundtrip • Montreal (YUL) - Chicago (ORD)YUL - ORD • 1 stop ORD - YUL • 1 stopCA $1,051CA $758found 1 day agoper traveller - Sheraton Grand Chicago Riverwalk
Dec 19 - Dec 23Sheraton Grand Chicago Riverwalk + Flight
Downtown Chicago4 nights4.0 star property8.6/10 - Excellent (1,875 reviews)Roundtrip • Hamilton (YHM) - Chicago (ORD)YHM - ORD • 1 stop ORD - YHM • 1 stopCA $2,739CA $1,191found 1 day agoper traveller - Park Hyatt Chicago
Dec 27 - Jan 2Park Hyatt Chicago + Flight
Downtown Chicago6 nights5.0 star property9.6/10 - Exceptional (1,001 reviews)"Given the price point and other reviews, we came here expecting a luxury stay similar to the Waldorf Astoria, Four Seasons, and Peninsula, which are some of our favorite properties to stay at. However, everything from the service and cleanliness to the ambiance of the entrance and lobby and the amenities (other than the gym, which was excellent) is best described as an upgraded version of an average Hilton, Hyatt, or Marriott. For example, there was a hair in the bed. When we reported it, the..."Reviewed November 4, 2026Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YTZ • Nonstop - The Emily Hotel
Jan 7 - Jan 11The Emily Hotel + Flight
Downtown Chicago4 nights4.0 star property9.2/10 - Wonderful (1,357 reviews)"Our stay at The Emily Hotel was outstanding! The entire property was well-maintained and the customer service provided by Leo and his team was excellent! We thoroughly enjoyed the offerings at Flora and were able to experience a Rooftop Cinema event! The hotel is conveniently located in walking distance to great restaurants and the L. I highly recommend The Emily Hotel and look forward to my stay during my next visit to Chicago!"Reviewed November 4, 2026Roundtrip • Montreal (YUL) - Chicago (ORD)YUL - ORD • 1 stop ORD - YUL • 1 stopCA $1,190CA $853found 1 day agoper traveller - Level Chicago Fulton Market
Jan 7 - Jan 11Level Chicago Fulton Market + Flight
Downtown Chicago4 nights4.0 star property9.2/10 - Wonderful (602 reviews)"If you are looking to stay in a condo type setting, this may be your spot. I checked in which you need to go through a process that takes 15 minutes, (do it before) and they automatically add a $25 per night fee for their gym and roof top. This was NOT published on Hotels.com or any other site. A total rip off as this is not a spa. There was no housekeeping. Checking in took 15 minutes in which there was little to no Wifi, so I had to go do this outside (crazy?). Do the check-in before..."Reviewed November 4, 2026Roundtrip • Montreal (YUL) - Chicago (ORD)YUL - ORD • 1 stop ORD - YUL • 1 stopCA $1,044CA $760found 1 day agoper traveller
Winfield Hotel Deals
"Staff was kind and helpful. The bed was very comfy and everything was clean."
"Hotel is in great shape. Friendly staff."
Fairfield Inn and Suites By Marriott Merrillville
Fairfield Inn and Suites By Marriott Merrillville
Hampton Inn by Hilton Merrillville
Hampton Inn by Hilton Merrillville"Meh~ very old and outdated Hampton."
"Awesome"
Home2 Suites by Hilton Merrillville
Home2 Suites by Hilton Merrillville
Towneplace Suites By Marriott Crown Point
Towneplace Suites By Marriott Crown Point
Country Inn & Suites by Radisson, Merrillville, IN
Country Inn & Suites by Radisson, Merrillville, INFrequently Asked Questions
How much does a Winfield vacation package cost?
Offering great value package deals from CA $758 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?
- 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.
- 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.
- 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.
- 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.