Winnetka 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 Winnetka Vacation
When a city adventure is calling, answer it with a Winnetka vacation package. With all your travel needs in place before you leave, all you have to do here is focus on making unforgettable memories. Fill your free time with tours of Chicago Botanic Garden, The Glen Club and North Shore Center for the Performing Arts, some of the attractions you simply have to see during your trip to Winnetka. Browse Expedia's wide range of travel options and begin planning your perfect vacation to Winnetka now.
Top Winnetka Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
CA $1,135
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,960 reviews)
I loved the room, the cleanliness, the ambiance, but I just think you should offer breakfast. Otherwise the place is great!
Reviewed on Aug 25, 2026
Swissotel - Chicago
Downtown Chicago
CA $1,360
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9/10 Wonderful! (3,553 reviews)
The views are nice. The room is more simple. The bathroom needs to be upgraded. Definitely just 3.5-4*. The late night snack area is a nice feature though.
Reviewed on Aug 25, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,313
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)
Nice place and location, especially if you have a good room. It's expensive but you get good experiance
Reviewed on Aug 26, 2026
Four Seasons Hotel Chicago
Downtown Chicago
CA $1,914
per person
Oct 9 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Amazing hotel in excellent location. We loved our stay and hope to return for another trip to Chicago.
Reviewed on Aug 23, 2026
Ready to book your vacation to Winnetka?
Winnetka Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $168
CA $200 total
Sep 7 - Sep 8
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $185
CA $220 total
Aug 30 - Aug 31
includes taxes & fees
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
CA $325
CA $370 total
Sep 18 - Sep 19
includes taxes & fees
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.
Stay near popular Winnetka attractions
Elder Lane Beach
Why not spend a lazy afternoon at Elder Lane Beach during your trip to Winnetka? Amble around the area's forest or visit its shops.
What to do in Winnetka
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
Frequently asked questions
How much does a Winnetka vacation package cost?
You'll find cheap prices from CA $1,135 on Expedia for your Winnetka getaway. However, a range of factors like the season, choice of hotel and length of stay will determine how much your vacation to Winnetka costs.
What are the cheapest months to go to Winnetka?
If you're hoping to book a cheap Winnetka vacation package, consider planning a trip in January, February and November. You'll usually find lower prices on flights and hotels during these months — ideal for budget-conscious travellers.
How many days is enough for Winnetka?
To get the most out of your Winnetka vacation, we recommend booking for 2 days. Split your time between discovering The Glen Club, Baha'i House of Worship and other well-known attractions, on top of experiencing neighbourhoods like Gross Point and North Evanston. If you've got some spare time, include a day trip in your Winnetka vacation itinerary.
How to find the best Winnetka package deals?
Use Expedia's handy filters to help you find some of the best Winnetka package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or browse for Winnetka package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Winnetka vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component separately. And you'll still get the flexibility to create a tailored Winnetka vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Winnetka?
If you're planning an impromptu Winnetka getaway, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Winnetka?
- Choose when to travel: Check your calendar and get packing. Your preferred season and the activities on offer will also help you decide when to escape to Winnetka.
- Budget wisely: As well as the cost of your hotel, you should factor in other expenses too. These include food, flights and transportation. Also, set aside a little extra for unexpected costs that may come up during your trip to Winnetka.
- Decide how many days away: Start by compiling a list of the attractions and activities you'd like to experience in Winnetka. Then, estimate how long you'll need at each, along with any travel time.
- Bundle your airfare and accommodations: Once you've nailed down your trip dates and duration, book the right Winnetka vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
