Winnetka Holidays

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Top Flight + Hotel Deals in Winnetka

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Pool fixed would be nicer.

Reviewed on 10 Aug 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
This was my first time staying. The staff was very friendly and helpful. Our room was very nice and perfectly located downtown. Also, the breakfast buffet was amazing and a nice surprise.

Reviewed on 9 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
Really nice and amazing location!! Would stay again!

Reviewed on 9 Aug 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (335 reviews)
A lot of good food options walkable distance.

Reviewed on 3 Aug 2025

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
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (1,991 reviews)
I liked this hotel, the rooms are cleaning and beautiful, the staff is nice, and the hotel is located near amazing restaurants, cafes, and tourist places.

Reviewed on 9 Aug 2025

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 €253 per night from 7 Sept to 8 Sept
€253
7 Sept - 8 Sept
includes taxes & fees
7.8/10 Good! (8,917 reviews)
Great stay.
"Hotel has old charm, which is a great change. a/c worked well to keep our room cool and great water pressure in the shower. Beds were comfortable and room was spacious. Location was top priority."

Reviewed on 7 Aug 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €196 per night from 22 Aug to 23 Aug
€196
22 Aug - 23 Aug
includes taxes & fees
8.2/10 Very Good! (1,836 reviews)
"The property if beautiful and historic. The main room is incredible. The rooms are well taken care of, you can just tell they are a little dated with a slight smell. I would definitely stay here again."

Reviewed on 8 Aug 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €155 per night from 24 Aug to 25 Aug
€155
24 Aug - 25 Aug
includes taxes & fees
8.4/10 Very Good! (3,632 reviews)
"Very Nice Staff"

Reviewed on 7 Aug 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,456 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.

Popular places to visit

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

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

Wrigley Field
Magnificent Mile - River North showing street scenes, signage and night scenes

Michigan Avenue

You can find the perfect gifts to bring home 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

Navy Pier

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

Navy Pier

What to do in Winnetka

River tour boat in Chicago

Architecture River Tour

€36
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

€39
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

€35
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Winnetka

Frequently asked questions

How much does a Winnetka holiday package cost?
Offering excellent value package deals from €805 on Expedia, you'll be pleasantly surprised at how much a holiday to Winnetka costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Winnetka?
January, February and November are the best times to search for cheap Winnetka holiday packages. Travelling in quieter periods means you can typically find lower prices on flights and hotels.
How many days is enough for Winnetka?
Typically, a handful of days is enough to explore the major sights during your Winnetka holiday. But if you prefer to have time to kick back or go on day tours, think about extending your itinerary.
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 holiday as a package?
An Expedia holiday 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 holiday package to Winnetka?
If you're considering a spontaneous Winnetka holiday, 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. Pick your travel dates: What you want to do in Winnetka and your favourite season can help you decide when to go.
  2. Figure out your budget: Ensure you have enough money to cover everything from food and transportation to airfares and activities. Your accommodation will likely be the biggest expense during your trip to Winnetka.
  3. Set the duration of your trip: Start by compiling a list of the attractions and activities you'd like to experience in Winnetka. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to find a Winnetka holiday package that brings all your bookings together.

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