A suburban street with a stone house, a tree, and a clear sky.

Winnetka Holidays from £720

Book a Hotel + Flight or Car together to unlock savings

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    Save up to £750 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Packages with flights are ATOL protected

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.
  • 20 Jan - 24 Jan

    Kimpton Gray Hotel by IHG + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (1,007 reviews)
    "I was surprised by the $29.50 daily charge for "Guest Amenity Fee". I did not ask for it. I don't even know what it is. I hate when hotels charge you hidden items."
    Reviewed November 9, 2026
    Return • London (LON) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 1 stop
    £898
    £720
    per traveller
    found 1 day ago
    Kimpton Gray Hotel by IHG
  • 25 Dec - 30 Dec

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.6/10 - Exceptional (2,082 reviews)
    "Amazing experience! Kurtis and Luis at concierge was great! I had a romantic arrangement in the room before arrival and they made it happen! Great great great 5 ✨"
    Reviewed November 9, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 2 stops
    £1,797
    £1,324
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago
  • 20 Jan - 24 Jan

    Pendry Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.2/10 - Wonderful (1,164 reviews)
    "The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back."
    Reviewed November 8, 2026
    Return • London (LON) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 1 stop
    £1,091
    £819
    per traveller
    found 1 day ago
    Pendry Chicago
  • 20 Jan - 24 Jan

    Viceroy Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (1,310 reviews)
    Return • London (LON) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 1 stop
    £1,202
    £956
    per traveller
    found 1 day ago
    Viceroy Chicago
  • 25 Dec - 30 Dec

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (3,902 reviews)
    "Upon arrival we were greeted immediately. The staff helped us unload our bags into a luggage cart and valet took the car to park. Our room was available for early check in. We stayed in the 7th floor in a single king room. Everything was clean and the views were great. We went up to the 22nd floor to see the river views from the rooftop bar. This hotel is in an absolute perfect location to see Chicago. You are close enough to walk to river walk, millennium park, the train, and magnificent mile...."
    Reviewed November 9, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 2 stops
    £1,021
    £827
    per traveller
    found 1 day ago
    LondonHouse Chicago, Curio Collection by Hilton

Discover the most popular places to visit in Winnetka

What to do in Winnetka

Winnetka Hotel Deals

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 travel package cost?

We make it easy to explore the world, with Winnetka travel packages starting from just £720. 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.