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.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
Oct 6 - Oct 10
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (652 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).

Reviewed on Jul. 27, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Oct 10 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,253 reviews)
The location of the hotel right off Michigan Avenue was perfect. Public parking right across the street. The hotel is fresh and new. Many staff available to assist. Do not skip the complimentary breakfast! I would easy pay $20 for that breakfast as it had everything from fresh fruit, real eggs, pastries, even a coffee cream warmer/frother machine for the great coffee!

Reviewed on Aug. 6, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on Jul. 26, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
Oct 10 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,049 reviews)
Amazing view, nice room sizes and very clean

Reviewed on Aug. 3, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 10 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Loved the attention to details that made the experience exceptional.

Reviewed on Aug. 6, 2025

Ready to book your vacation to Winnetka?

 

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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 1 to Sep 2
CA $185
CA $217 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (8,981 reviews)
"I love it"

Reviewed on Aug. 5, 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $239 per night from Aug 22 to Aug 23
CA $239
CA $315 total
Aug 22 - Aug 23
includes taxes & fees
8.2/10 Very Good! (1,830 reviews)
"Love the gym!"

Reviewed on Aug. 5, 2025

Palmer House a Hilton Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is CA $201 per night from Aug 24 to Aug 25
CA $201
CA $236 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,351 reviews)
"I liked the in and out parking access for one rate per day."

Reviewed on Aug. 6, 2025

Crowne Plaza Chicago West Loop by IHG
See all 4,577 properties in Winnetka
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Winnetka

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Winnetka

River tour boat in Chicago

Architecture River Tour

CA $57
per adult
96% of travellers recommend
Architecture River Tour
Couple on a sightseeing boat in Chicago

Skyline Lake Tour

CA $41
per adult
92% of travellers recommend
Skyline Lake Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

CA $62
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
See all activities in Winnetka

Frequently asked questions

How much does a Winnetka vacation package cost?
You'll find cheap prices from CA $1,051 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.