Winnetka Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to CA $775 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    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.

Top Winnetka Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Nov. 16 - Nov. 20
found 6 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (457 reviews)
We want to come back in the future if we receive the same service then I will confirm my appreciation firmly...

Reviewed on Sep. 23, 2024

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Nov. 5 - Nov. 11
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8/10 Very Good! (1,051 reviews)
No microwave in my room 605. I dont like that.

Reviewed on Sep. 21, 2024

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Nov. 5 - Nov. 11
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,137 reviews)
Never have any complaints when staring at The Virgin. The rooms are clean and quiet and the rain shower is amazing!

Reviewed on Sep. 22, 2024

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Nov. 16 - Nov. 20
found 6 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.6/10 Excellent! (1,529 reviews)
The property was in a great location with lots of affordable parking options. The staff was accommodating. The room was clean.

Reviewed on Sep. 20, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Nov. 16 - Nov. 20
found 6 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (1,364 reviews)
It was an absolutely amazing hotel and I was so glad we picked Trump Tower! The staff was absolutely amazing, kind and helpful. The room was beautiful, extremely clean and the view was amazing. We will be back there for sure.

Reviewed on Sep. 23, 2024

Ready to book your vacation to Winnetka?

 

Choose your dates

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
The price is CA $185 per night from Oct. 1 to Oct. 2
CA $185
CA $217 total
includes taxes & fees
Oct 1 - Oct 2
7.6/10 Good! (7,858 reviews)
"Great stay!"

Reviewed on Sep. 22, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $166 per night from Sep. 29 to Sep. 30
CA $166
CA $195 total
includes taxes & fees
Sep 29 - Sep 30
8.6/10 Excellent! (3,408 reviews)
"Very clean room, shower water pressure was actually amazing, and really helpful after my 21 hour day! Pedro at the front desk was very helpful, super polite, great first impression for this hotel! Would definitely recommend this hotel!"

Reviewed on Sep. 21, 2024

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $271 per night from Oct. 1 to Oct. 2
CA $271
CA $319 total
includes taxes & fees
Oct 1 - Oct 2
8.6/10 Excellent! (2,557 reviews)
"Check in went smoothly and the staff member was excellent."

Reviewed on Sep. 20, 2024

Eurostars Magnificent Mile
See all 3,778 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

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Winnetka vacation package cost?
We make it easy to travel the world, with Winnetka vacation packages starting from as little as CA $928. You’ll have the flexibility to combine your favorite airlines, hotels and car rental. For the ultimate getaway, why not add a few tours and experiences to your travel itinerary?
How do I get a cheap travel package to Winnetka?
Bundle your flights and hotels, toss in extras such as a rental car or activities, and save with a Winnetka vacation package. You won’t just score superb discounts on your getaway — you’ll have a world of choice within your reach too. When you book through Expedia, you can select from more than 550 air carriers and 1,000,000 properties worldwide. Your unforgettable vacation starts right here, right now!
Where should I stay in Winnetka?
A vacation in Winnetka wouldn’t be complete without visiting Wagner Farm, Langdon Park Beach and Elder Lane Beach. Spend your nights close to these popular attractions and make sightseeing easy.
How far in advance should I book my Winnetka vacation?
Smart travelers will likely want to book early. You can generally compare international fares on Expedia up to a year before your flight. If you’re purchasing your ticket at the last minute, fear not. Discounted prices sometimes occur just weeks prior to departure.
What does an Expedia Winnetka travel package include?
It comes down to what you’re looking for. If you’re traveling solo, you might decide to bundle hotels and flights. Taking the whole family to Winnetka? A travel package that includes flights, hotels and rental cars might suit you better. Expedia gives you the freedom to tailor your travel package.
What should I know before booking a Winnetka travel package?
Whether it’s relaxation or adventure you’re chasing, a Winnetka vacation package lets you plan your escape your way. Plus, you’ll score great discounts just for combining your accommodations with your rental car and flights. The more you bundle, the bigger the savings!
Can I choose my airline with a Winnetka Expedia vacation package?
Yes — and it’s simple too. Expedia has access to more than 550 partner airlines globally. Our packages give you the freedom to take your pick of available flights, hotels and activities that fit your needs.
If I'm not able to travel, can I cancel my Winnetka vacation package?
Because we understand life is full of surprises, the answer is yes. To learn more, head to our Customer Service Portal. But generally speaking, if you’ve booked your Winnetka vacation package in the last 24 hours, you may be able to change or cancel it free of charge. Your airline, hotel or car rental company may charge a fee if your booking is older than that.

Discover the most popular places to visit in Winnetka

Image for McCormick Place

McCormick Place

4.5/5(141 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Image for Michigan Avenue

Michigan Avenue

4.5/5(19 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
Image for Navy Pier

Navy Pier

4.5/5(459 reviews)

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

Navy Pier

What to do in Winnetka

Image for Flyover in Chicago

Flyover in Chicago

CA $38
Per adult
96% of travellers recommend
Flyover in Chicago
Image for Architecture River Tour from Navy Pier

Architecture River Tour from Navy Pier

CA $62
Per adult
94% of travellers recommend
Architecture River Tour from Navy Pier
Image for Chicago by Night: 90 Minute River and Lakefront Cruise

Chicago by Night: 90 Minute River and Lakefront Cruise

CA $57
Per adult
86% of travellers recommend
Chicago by Night: 90 Minute River and Lakefront Cruise
See all activities in Winnetka

Other vacations you might like

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