Winnetka Vacation Packages

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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.
The Allegro Royal Sonesta Hotel Chicago Loop
Trump International Hotel & Tower Chicago
Park Hyatt Chicago
Staypineapple, An Iconic Hotel, The Loop
Level Chicago – Old Town

Ready to book your vacation to Winnetka?

 

Choose your dates

Winnetka Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Sep 2 to Sep 3
CA $185
CA $218 total
Sep 2 - Sep 3
includes taxes & fees
7.8/10 Good! (8,961 reviews)
"Its location is the main reason why I chose to stay. The room has been updated; it is roomy and clean. Staffs are very friendly and helpful."

Reviewed on Aug. 17, 2025

Congress Plaza Hotel
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Sep 1 to Sep 2
CA $208
CA $245 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,201 reviews)
"I asked for a microwave and they said they would bring it to the room and it was never delivered, other than that, the stay was very comfortable and convenient."

Reviewed on Aug. 18, 2025

The Wade
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
The price is CA $222 per night from Sep 3 to Sep 4
CA $222
CA $260 total
Sep 3 - Sep 4
includes taxes & fees
8.4/10 Very Good! (4,711 reviews)
"Happy Hour drinks were amazing!"

Reviewed on Aug. 16, 2025

Embassy Suites by Hilton Chicago Downtown River North
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.

Frequently asked questions

How much does a Winnetka vacation package cost?
You'll find cheap prices from CA $479 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.