Winnetka Trips (flight + hotel)

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Top hotels in Winnetka

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 P5,055 per night from 24 Nov to 25 Nov
P5,055
P5,934 total
includes taxes & fees
Nov 24 - Nov 25
7.8/10 Good! (8,124 reviews)
Great hotel
"Very beautiful hotel. Friendly, competent staff. The room is comfortable. It would be better if the temperature of the air conditioner can be controlled."

Reviewed on Nov 20, 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 P5,876 per night from 23 Dec to 24 Dec
P5,876
P6,897 total
includes taxes & fees
Dec 23 - Dec 24
8.6/10 Excellent! (3,547 reviews)
"I loved the view from my room! I loved that it is right in the middle of Downtown!!! I would stay here again."

Reviewed on Nov 21, 2024

River Hotel
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is P5,660 per night from 23 Dec to 24 Dec
P5,660
P6,645 total
includes taxes & fees
Dec 23 - Dec 24
8.4/10 Very Good! (3,264 reviews)
"This is a go-to hotel for me near a yearly event I participate in. It's the best value of any of the hotels in its immediate surrounding area."

Reviewed on Nov 21, 2024

Club Quarters Hotel, Central Loop, Chicago
See all 4,113 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.

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 . 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.

Popular places to visit

McCormick Place

McCormick Place

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
United Center

United Center

Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

United Center
Millennium Park showing modern architecture, autumn leaves and street scenes

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

What to do in Winnetka

Flyover in Chicago

Flyover in Chicago

P2,217
Per adult
94% of travellers recommend
Flyover in Chicago
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

P2,594
Per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
River tour boat in Chicago

Architecture River Tour

P3,130
Per adult
94% of travellers recommend
Architecture River Tour
See all activities in Winnetka
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.