Winnetka Vacations from $636

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was $1,057, price is now $636 per person
$636
per person
Jun 4 - Jun 8
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 $1,559, price is now $816 per person
$816
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Great location right off of Michigan Ave. They have a very good breakfast, that included almost everything you could want. It was very popular and packed with people. One negative, it felt like it was a cafeteria and not a relaxing place to sit down, relax and enjoy.

Reviewed on Mar 9, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $1,506, price is now $895 per person
$895
per person
Jun 4 - Jun 8
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

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was $1,258, price is now $753 per person
$753
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,070 reviews)
Very nice & clean hotel and near the Bean and shops are walkable.

Reviewed on Mar 3, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was $1,426, price is now $880 per person
$880
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,613 reviews)
Every thing was amazing the staff was friendly and helpful shops and everything was close by I loved it thank you again

Reviewed on Mar 9, 2026

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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
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

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

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! (9,936 reviews)
Good: Clean; friendly staff. Bad: hot water stopped working at some point; safe was not working; lightbulb kept flickering; ice machine was broken on the 10th floor

Reviewed on Mar 9, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$162 nightly
The price is $190 total per night from Mar 18 to Mar 19
$190 total
Mar 18 - Mar 19
Total with taxes and fees
9.4/10 Exceptional! (3,497 reviews)
Great location right off of Michigan Ave. They have a very good breakfast, that included almost everything you could want. It was very popular and packed with people. One negative, it felt like it was a cafeteria and not a relaxing place to sit down, relax and enjoy.

Reviewed on Mar 9, 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! (5,742 reviews)
The breakfast menu was excellent. The hotel had a small pool and gym in a nice location. The room was clean and well-equipped with a refrigerator, coffee machine, and microwave. The bathroom was luxurious with Crab Tree The staff was friendly, and it was close to everything. However, there was no ...

Reviewed on Mar 9, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,639 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

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Frequently asked questions

How much does a Winnetka vacation package cost?
Offering excellent value package deals from $636 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.

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