Winnetka Holidays from £1,063
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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.
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
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
£167
25 Oct - 26 Oct
includes taxes & fees
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£134
25 Oct - 26 Oct
includes taxes & fees
8/10 Very good! (10,219 reviews)
"I was in a North wing and was here for one night. The property looks old. The room was tidy but smelling. There is no temperature control I could find in the room. Only Fan On/off. The TV in the room is very small. The bathroom fan was making lot of noise and there is only one switch for the bathroom ..."
Reviewed on 25 Sept 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
£120
27 Sept - 28 Sept
includes taxes & fees
8/10 Very good! (2,341 reviews)
"Loved my stay the staff was nice and the location was great."
Reviewed on 25 Sept 2026
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.
Stay near popular Winnetka attractions
Maple Street Beach
Why not spend a lazy afternoon at Maple Street Beach during your trip to Winnetka? Amble around the area's forests or visit its shops.
Elder Lane Beach
This lakefront sanctuary offers a serene escape with pristine sandy shores and Lake Michigan views. Enjoy a peaceful afternoon in the adjacent park with its well-maintained picnic areas and playground.
What to do in Winnetka
Skydeck Chicago at Willis Tower
£32
per adult
88% of travellers recommend
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 £1,063. 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.
Explore a world of travel with Expedia
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- Winnetka Hotels
- Flights to Chicago
- Flights to Evanston
- Flights to Glencoe
- Flights to O'Hare Intl.
- Flights to Skokie
- Flights to Wilmette
- Flights to Winnetka
- Flights from O'Hare Intl.
- American Airlines Dublin (DUB) to Chicago (ORD) flights
- American Airlines London (LHR) to Chicago (ORD) flights
- British Airways London (LHR) to Chicago (ORD) flights
- Virgin Atlantic London (LHR) to Chicago (ORD) flights
- Virgin Atlantic Manchester (MAN) to Chicago (ORD) flights
- Flights from Golf
- Flights from Birmingham (BHX) to Chicago (ORD)
- Flights from Columbus (CMH) to Chicago (ORD)
- Flights from Dublin (DUB) to Chicago (ORD)
- Flights from Edinburgh (EDI) to Chicago (ORD)
- Flights from Glasgow (GLA) to Chicago (ORD)
- Flights from New York (JFK) to Chicago (ORD)
- Flights from Los Angeles (LAX) to Chicago (ORD)
- Flights from New York (LGA) to Chicago (ORD)
- Flights from London (LGW) to Chicago (ORD)
- Flights from London (LHR) to Chicago (ORD)
- Flights from Manchester (MAN) to Chicago (ORD)
- Flights from San Diego (SAN) to Chicago (ORD)
- Flights from Sacramento (SMF) to Chicago (PWK)
- Flights from Tulsa (TUL) to Chicago (ORD)
- Flights from Toronto (YYZ) to Chicago (ORD)
- Art Institute of Chicago
- Visit Norwood Park East
- Chicago Riverwalk
- Visit Rogers Park
- Visit The Loop
- Chicago Theatre
- Chicago Water Tower
- Chicago Holidays
- Visit Chicago
- Downtown Chicago Holidays
- Ernest Hemingway Museum and House
- Visit Evanston
- Garfield Park Conservatory
- Golf Holidays
- Grant Park
- Home Alone House
- Lake Forest Holidays
- Lakeview Holidays
- Legoland® Discovery Center
- Lincoln Hall
- Lincoln Park Conservatory
- Lincoln Park Zoo
- Lincoln Park Holidays
- Lincolnshire Holidays
- Michigan Avenue
- Millennium Park
- Montrose Beach
- Navy Pier
- Visit North Suburbs
- Northwestern University
- Rosemont Holidays
- Shops at North Bridge
- Unity Temple
- Willis Tower
- Visit Winnetka
- Woodfield Mall
- Wrigley Field
* 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.
