Winnetka Holidays from £928

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Your Winnetka Holiday

When a city adventure is calling, answer it with a Winnetka holiday 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 Centre 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 holiday to Winnetka now.

Top Winnetka Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
15 Sept - 20 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (652 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).

Reviewed on 27 Jul 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
15 Sept - 20 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on 22 Jul 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
17 Sept - 24 Sept
found 21 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,149 reviews)
I’d like to give props to the housekeepers the most. Anything I used, that product was replaced. Very attentive.

Reviewed on 5 Aug 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
per person
25 Oct - 1 Nov
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (270 reviews)
walkable to many desireable places.

Reviewed on 16 Jul 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
15 Sept - 20 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on 26 Jul 2025

Winnetka Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
12,500
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Rosemont Theatre, Parkway Bank Park Entertainment District and Montrose Beach

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 £118 per night from 6 Aug to 7 Aug
£118
6 Aug - 7 Aug
includes taxes & fees
7.8/10 Good! (8,974 reviews)
"Great location! Rooms are newly renovated and nice."

Reviewed on 5 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 £172 per night from 22 Aug to 23 Aug
£172
22 Aug - 23 Aug
includes taxes & fees
8.2/10 Very Good! (1,820 reviews)
"Beautiful gilded age feel. Long wait for elevators is my only complaint"

Reviewed on 3 Aug 2025

Palmer House a Hilton Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is £129 per night from 24 Aug to 25 Aug
£129
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (1,345 reviews)
"My wife and daughter loved there was a Starbucks a short walk down the street, maybe 5 minutes, this was their morning routine. The restaurant was good, prices were in line with other spots in the area, however, I did not like being told the restaurant closes at 9:30, even though hours say 10. Not ..."

Reviewed on 5 Aug 2025

Crowne Plaza Chicago West Loop by IHG
See all 4,577 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

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 which includes 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

£31
per adult
96% of travellers recommend
Architecture River Tour
Couple on a sightseeing boat in Chicago

Skyline Lake Tour

£22
per adult
92% of travellers recommend
Skyline Lake Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

£33
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
See all activities in Winnetka

Frequently asked questions

How much does a Winnetka travel package cost?
We make it easy to explore the world, with Winnetka travel packages starting from just £928. You'll have the flexibility to bundle your favourite airlines, hotels and car rental. For the ultimate escape, why not add a couple of tours and activities to your travel itinerary?
If I'm not able to travel, can I cancel my Winnetka travel package?
You can cancel your Winnetka booking if your travel plans have been upended. Whether you'll incur a fee or not depends on your hotel, airline or car rental company. You may be able to change or cancel for free if you booked in the last 24 hours. Visit our Customer Service Portal for more information.
How do I get a cheap travel package to Winnetka?
Booking a Winnetka travel package with Expedia is a smart way to save. We have access to more than 550 air carriers and 1,000,000 hotel options all over the world. With such a wonderful range to choose from, you'll have no issues putting together your next dream holiday.
Does Expedia offer Book Now, Pay Later Winnetka holidays?
Yes. Expedia has partnered with online lender Klarna to help you easily pay for your holiday in instalments. Simply select the payment plan that suits best during the checkout process and take away the stress of budgeting for your next trip. Make sure you bundle your flights, car hire and hotel with Expedia to get the biggest bang for your travel buck. Check out our flexible payment options below:

  • Pay monthly holidays: Jet off on that dream holiday sooner with Klarna's convenient monthly instalment plans. If paying just a little each month works for you, choose this option at checkout.
  • Pay in instalments holidays: If you want to pay for your escape in multiple transactions, holidays paid in instalments might be the best option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: When you see an amazing deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you lock in your escape.

Where should I stay in Winnetka?
With lots to discover in Winnetka, we suggest you stay close to its attractions. Wagner Farm, Writers Theatre and Kenilworth Beach are some popular ones to add to your must-see list.
What are the top hotels in Winnetka?
Lock in a room at Hyatt Regency Chicago. It's one of this area's most sought-after hotels. Another top option in Winnetka is The Godfrey Hotel Chicago.
How far in advance should I book my Winnetka holiday?
While not all air carriers release tickets early, you can normally look up international flights on Expedia up to a year in advance. This is when you'll score some fantastic deals. If you're booking last minute, you may still be in luck. Sometimes the cheapest prices appear a few weeks prior to departure.
What does an Expedia Winnetka travel package include?
With Expedia, you can choose a combination of car rentals, flights and hotels to build your perfect Winnetka travel package. Once you've made your booking, you can add on fun stuff like sightseeing tours and activities. Don't forget — the more you bundle, the bigger the savings!
What should I know before booking a Winnetka travel package?
Discover deals that suit your budget with an Expedia package. Hotels, airfares, rental cars — we have them all. You'll save a tidy sum just by bundling your bookings. Whether you're embarking on a winter snow adventure or getting some sun on a warm beach, your ideal getaway is just a few clicks away.
Can I choose my airline with a Winnetka Expedia travel package?
With a travel package, you're always in charge. Whether you'd prefer to fly to Winnetka in coach or first class, simply pick from the available airline options. Expedia has access to over 550 partner airlines throughout the world.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.