Winnetka Vacations from $786

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, 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.

The Latest Winnetka vacation packages

Price found within the past 48 hours. Click for updated prices.
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 $1,361, price is now $786 per person
$786
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,573 reviews)
the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well. The location is excellent and i would go back.

Reviewed on Mar 4, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,900, price is now $946 per person
$946
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Everything was great, except for the rooftop that was not open because which was the main reason we chose this hotel

Reviewed on Mar 10, 2026

The Wade

The Wade

4.5 out of 5
Downtown Chicago
Price was $1,645, price is now $904 per person
$904
per person
May 13 - May 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,705 reviews)
Room decent. Bartendars very friendly.

Reviewed on Mar 10, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was $2,194, price is now $1,279 per person
$1,279
per person
May 13 - May 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,613 reviews)
My stay at LondonHouse Chicago was absolutely amazing from start to finish. The hotel itself is beautiful and perfectly located, offering stunning views of the river and city skyline. The restaurants were excellent, with delicious food and a great atmosphere. The rooftop experience was definitely a highlight and made the stay feel even more special. I also had the chance to visit the spa, which was incredibly relaxing and well done. The environment was peaceful, the service was top-tier, and it was the perfect way to unwind during my trip. Overall, everything—from the service to the amenities—was exceptional. I would definitely book again and highly recommend LondonHouse Chicago to anyone visiting the city. ⭐⭐⭐⭐⭐

Reviewed on Mar 10, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,393, price is now $835 per person
$835
per person
May 26 - May 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (436 reviews)
Great value, friendly staff

Reviewed on Mar 8, 2026

Don't see what you're looking for?
See all available trips from Columbus to Winnetka
View all trips

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

Discover the most popular places to visit in Winnetka

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

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

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

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 featuring a sunset and rides

Navy Pier

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

Navy Pier

What to do in Winnetka

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$26
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

$44
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$61
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
See all activities in Winnetka

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
$101 nightly
The price is $118 total per night from Apr 1 to Apr 2
$118 total
Apr 1 - Apr 2
Total with taxes and fees
8/10 Very Good! (9,942 reviews)
I like this hotel. It’s simple, clean, no frills and gets the job done. Hallways carpets are a little worse for wear but the room serves the purpose - you get what you reserve! - and you’re close to everything. It’s a “go to” for me.

Reviewed on Mar 10, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
$162 nightly
The price is $190 total per night from Mar 24 to Mar 25
$190 total
Mar 24 - Mar 25
Total with taxes and fees
9.4/10 Exceptional! (3,509 reviews)
Clean, amazing terrace, bad and breakfast.

Reviewed on Mar 10, 2026

Hotel Riu Plaza Chicago
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
$122 nightly
The price is $143 total per night from Mar 22 to Mar 23
$143 total
Mar 22 - Mar 23
Total with taxes and fees
8.6/10 Excellent! (5,725 reviews)
Great location. Room was very hot. U can't switch heat to AC in the rooms. U just have to deal with what the hotel has it on. Also they would only give us one little fan to cool off. Not 2 which I'm sure they had plenty of. Other then that no complaints. They give a free happy hour with 2 free drinks ...

Reviewed on Mar 11, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,614 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.

Find the Best Winnetka Vacation Packages

Winnetka Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
12,500
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Rosemont Theatre, Parkway Bank Park Entertainment District and Montrose Beach

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Winnetka vacation package cost?
Offering excellent value package deals from $786 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.