Winnetka Vacations from $426

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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
Save 100% on your flight
Price was $694, price is now $426 per person
$426
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,809 reviews)
Staff were great but the room was much smaller than expected. There was a desk in room which was unnecessary and it took up so much of the walk that the bar fridge and microwave stacked on top of it stuck out past the wall and ended up being a tripping hazard.

Reviewed on Jul 18, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $898, price is now $559 per person
$559
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Save 100% on your flight
Price was $717, price is now $480 per person
$480
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (657 reviews)
We were greeted by the GM. Felt like coming to my favorite Aunt’s home. Staff checked in several times to make sure all was well. The GM was at breakfast both mornings and Rene other reason for our stay. It was a concert and she wanted to know if we enjoyed it. Who does that at a hotel?! By fa the best hotel we have ever stayed at. Oh, and if you’re worried about walking back from the United Center, don’t. Very well lit and lots of people. Very safe

Reviewed on Jul 17, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $800, price is now $541 per person
$541
per person
Sep 6 - Sep 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
Good location. Expensive parking

Reviewed on Jul 17, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $867, price is now $592 per person
$592
per person
Aug 21 - Aug 23
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (501 reviews)
Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place.

Reviewed on Jul 14, 2026

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Stay near popular Winnetka attractions

Chocolate Box

Enjoy a stop at Chocolate Box, an entertaining place to visit in Winnetka. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
See properties

What to do in Winnetka

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$22
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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 all activities in Winnetka

Winnetka Hotel Deals

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $204 total per night from Aug 8 to Aug 9
$204 total
Aug 8 - Aug 9
Total with taxes and fees
Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$181 nightly
The price is $215 total per night from Jul 19 to Jul 20
$215 total
Jul 19 - Jul 20
Total with taxes and fees
8.2/10 Very Good! (1,773 reviews)
"Overall, the service was decent, but I was disappointed by how my situation was handled. When I arrived at the hotel, I realized that I had accidentally booked the correct dates but the wrong month. The staff told me to make a new reservation for the correct dates and assured me that the payment ..."

Reviewed on Jul 18, 2026

The Chicago Hotel Collection Ambassador Gold Coast
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Fully refundableReserve now, pay when you stay
$254 nightly
The price is $302 total per night from Aug 9 to Aug 10
$302 total
Aug 9 - Aug 10
Total with taxes and fees
8.6/10 Excellent! (1,927 reviews)
"Well... when we got there the rooms weren't ready and we had to wait over 4 hours until we finally got our rooms ready at 9 pm. There was no water in my room. And the room AC was very loud and the constant elevator noise while it moved up and down throughout the night... felt like sleeping next to ..."

Reviewed on Jul 18, 2026

The Wade
See all 4,331 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 $426 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.