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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was CA $862, price is now CA $568 per person
CA $568
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Everything was nice!!

Reviewed on Aug. 23, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,660, price is now CA $1,011 per person
CA $1,011
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on Aug. 19, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $914, price is now CA $582 per person
CA $582
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (335 reviews)
Great except parking

Reviewed on Aug. 19, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,021, price is now CA $667 per person
CA $667
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
Will be coming back! Beautiful rooms and great staff.

Reviewed on Aug. 24, 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,291, price is now CA $845 per person
CA $845
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.

Reviewed on Aug. 21, 2025

Ready to book your vacation to Winnetka?

 

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Winnetka Hotel Deals

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 $209 per night from Sep 1 to Sep 2
CA $209
CA $245 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,218 reviews)
"Friendly"

Reviewed on Aug. 24, 2025

The Wade
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 $168 per night from Aug 26 to Aug 27
CA $168
CA $198 total
Aug 26 - Aug 27
includes taxes & fees
7.8/10 Good! (8,992 reviews)
"Transportation by bus or subway is within a 5 minute walk, very easy. Hotel is across from a beautiful park. Lobby is nice but the hallways look very rough. It’s an old hotel with basic upgrades. Rooms were clean but shows it age. Beds were comfy. We checked our luggage upon arrival because our room ..."

Reviewed on Aug. 23, 2025

Congress Plaza Hotel
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
Fully refundableReserve now, pay when you stay
The price is CA $210 per night from Sep 3 to Sep 4
CA $210
CA $247 total
Sep 3 - Sep 4
includes taxes & fees
8.4/10 Very Good! (4,752 reviews)
"Great location. Nice size rooms. Breakfast was really good, only way to busy and crowded during that experience. They should extend the breakfast hours by an hour to reduce the over crowding. Overall good stay. Would return.."

Reviewed on Aug. 23, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,480 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
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Family Vacations
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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
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $56
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
96% of travellers recommend
Chicago By Night River & 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 $568 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.