Winnetka Vacations from $156

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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.

The Latest Winnetka vacation packages

Price found within the past 48 hours. Click for updated prices.
Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Save 100% on your flight
Price was $261, price is now $156 per person
$156
per person
Oct 30 - Nov 2
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.2/10 Very Good! (384 reviews)
I like the place, it is very quiet and safe, but the room requires better cleaning, the balcony was not clean and blinds need to be washed, anyhow i liked it.

Reviewed on Aug 21, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $1,322, price is now $641 per person
$641
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on Aug 22, 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
Save 100% on your flight
Price was $1,180, price is now $631 per person
$631
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,087 reviews)
I give this hotel five stars. A very clean atmosphere. The staff is amazing, the valet workers knew my name, but the best was when I opened that door and seen that window view. It was amazing, gorgeous absolutely beautiful!! I would definitely stay again and tell people what a great experience I had here!

Reviewed on Aug 24, 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $945, price is now $557 per person
$557
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,061 reviews)
Amazing service and friendly staff! Great place and within walkable distances to near by shops.

Reviewed on Aug 23, 2025

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,030, price is now $621 per person
$621
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (3,059 reviews)
Loved the property, big size room and very cool decoration! Great location

Reviewed on Aug 22, 2025

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Discover the most popular places to visit in Winnetka

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

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

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

Michigan Avenue

4.5/5(332 reviews)

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 featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

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

$41
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

$41
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

$45
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Winnetka

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
$151 nightly
The price is $177 total per night from Sep 1 to Sep 2
$177 total
Sep 1 - Sep 2
Total with taxes and fees
8.2/10 Very Good! (1,211 reviews)
"The room and view were super nice. Even with not being on the waterfront side of the build we werent disappointed. Check in staff could be nicer but the bar staff was excellent. Nice and informative for travelers. The pier was i. Walking distance. Food and shopping all around and spotless insude ..."

Reviewed on Aug 20, 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
$143 nightly
The price is $168 total per night from Aug 25 to Aug 26
$168 total
Aug 25 - Aug 26
Total with taxes and fees
7.8/10 Good! (8,982 reviews)
"Experience what it must have felt like to attend the 1893 Worlds Fair"

Reviewed on Aug 22, 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
$152 nightly
The price is $179 total per night from Sep 3 to Sep 4
$179 total
Sep 3 - Sep 4
Total with taxes and fees
8.4/10 Very Good! (4,736 reviews)
"Great location for a quick getaway"

Reviewed on Aug 21, 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.

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Frequently asked questions

How much does a Winnetka vacation package cost?
Offering excellent value package deals from $156 on Expedia, you'll be pleasantly surprised at how much a vacation to Winnetka costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Winnetka?
You can typically find reduced prices and better availability in December, January and February. Check out our cheap Winnetka vacation packages and you could land some great off-season deals.
How many days is enough for Winnetka?
The ideal duration for your Winnetka vacation depends on what you'd like to do. Typically, a few days to a week will give you enough time to hit all the main attractions and explore some hidden gems along the way.
How to find the best Winnetka package deals?
Begin your search for a Winnetka package deal by entering your travel dates and destination under our "Packages" tab. Then select a few filters, like "Guest rating" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Winnetka package deal straight away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Winnetka getaway off to a flying start.
Is it cheaper to book a Winnetka vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and hotels individually. Better still, you can tailor your Winnetka getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Winnetka?
If you're considering a spontaneous Winnetka vacation, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Winnetka?

  1. Choose when to travel: Check your schedule and get your bags packed. Your favorite season and the type of activities on offer will also help you decide when to vacation in Winnetka.
  2. Calculate your budget: Make sure you have enough money to pay for everything from transportation and food to activities and flights. Your hotel will probably be the biggest expense during your trip to Winnetka.
  3. Organize your Winnetka getaway with Expedia's trip planning tool: Look for and book stays and experiences all in one place. You can also collaborate with your group to plan an unforgettable trip to Winnetka together.
  4. Determine how many days away: Start by making a list of all the activities and sights you'd like to get to in Winnetka. Then, estimate how long you'll need at each, along with any travel time.
  5. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a customized Winnetka vacation package.
  6. Add on excursions and experiences: Take a look at our dedicated travel guide to find some incredible things to do in Winnetka in Winnetka. Book tickets or make reservations before you go to save time and avoid the stress of trying to find activities once you arrive.

Does Expedia offer Book Now, Pay Later Winnetka vacation packages?
If you're anything like us, you love jet-setting around the world but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Winnetka break over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.