A dirt path flanked by leafless trees, leading towards a distant building.

Willow Springs Holidays from £1,281

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Packages with flights are ATOL protected

Top Willow Springs flight + hotel deals

Price found within the past 48 hours. Click for updated prices.
  • 12 Oct - 17 Oct

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.4/10 - Exceptional (4,763 reviews)
    "Excellent!!"
    Reviewed July 21, 2026
    Return London (LON) - Chicago (ORD)
    LHR - ORDDirect ORD - LHR1 stop
    £1,858
    £1,281
    per traveller
    found 1 day ago
    Hotel Riu Plaza Chicago
  • 20 Sept - 23 Sept

    Four Seasons Hotel Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.4/10 - Exceptional (1,002 reviews)
    "EXCELLENT STAFF, UPGRADED ROOM AMENITIES. EVERYTHING YOU WOULD EXPECT FROM A FOUR SEASONS"
    Reviewed July 20, 2026
    Return London (LHR) - Chicago (ORD)
    LHR - ORDDirect ORD - LHR1 stop
    Save 100% on your flight
    £2,729
    £1,905
    per traveller
    found 21 hours ago
    Four Seasons Hotel Chicago
  • 12 Oct - 17 Oct

    The Emily Hotel + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.2/10 - Wonderful (1,320 reviews)
    Return London (LON) - Chicago (ORD)
    LHR - ORDDirect ORD - LHR1 stop
    £1,996
    £1,436
    per traveller
    found 1 day ago
    The Emily Hotel
  • 12 Oct - 17 Oct

    Fairmont Chicago at Millennium Park + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    8.8/10 - Excellent (2,267 reviews)
    "The staff was extremely friendly and professional. They were knowledgeable about the surroundings and able to give relevant advice to get around and places to see thank you"
    Reviewed July 21, 2026
    Return London (LON) - Chicago (ORD)
    LHR - ORDDirect ORD - LHR1 stop
    £1,992
    £1,457
    per traveller
    found 1 day ago
    Fairmont Chicago at Millennium Park
  • 12 Oct - 17 Oct

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.4/10 - Exceptional (2,607 reviews)
    Return London (LON) - Chicago (ORD)
    LHR - ORDDirect ORD - LHR1 stop
    £1,911
    £1,425
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton

Willow Springs 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

Why should I book my Willow Springs holiday with Expedia?

Expedia has your back for all aspects of your upcoming Willow Springs holiday. You'll always get the best deals around, but when you bundle your flights, accommodation and/or hire car into a holiday package, you'll get even more savings. Looking to really make the most of your escape? Add a few exciting tours and activities to your package. Expedia offers flexible cancellation policies on most bookings, so you won't need to worry if your plans change. Visit our Customer Service Portal link to learn more.

When is the best time of year to holiday in Willow Springs?

Willow Springs draws the crowds in March, May and June. If you want a more relaxed holiday, go there in December, January and February. With average daytime temperatures of -4ºC, January is the coolest period in Willow Springs. The warmest time of year is July, when you can expect average temperatures of 23ºC throughout the day. Whatever the weather, you'll discover plenty to keep you busy here.

What is the top hotel for my holiday in Willow Springs?

Unwind in Willow Springs by choosing LondonHouse Chicago, Curio Collection by Hilton as your home-away-from-home and gateway to adventure and exploration.

How do I get a cheap holiday to Willow Springs?

Search for flights that suit your schedule, add a hotel room to your booking and watch the savings rack up with a Willow Springs holiday. It's that easy! From flights and hotels to hire cars and activities, Expedia makes travelling on a budget easy. And with more than 400 airlines and 321,000 properties all over the world to pick from, you'll never be short of choice. Learn more about how you can save money on your holiday when you combine your hotel and flight bookings with Expedia.

What should I do on my Willow Springs holiday?

Make sure your holiday in Willow Springs is one to remember by checking out its leading attractions. Brookfield Zoo, SeatGeek Stadium, Oakbrook Centre Mall and Cog Hill Golf & Country Club are just some of the things to put on your itinerary while you're in the city.

Do I need a visa for my Willow Springs holiday?

Research the most up-to-date information on official government websites. Your nationality and whether you're visiting for study, business or leisure will determine if you'll need a visa for Willow Springs. Make yourself familiar with the application process, including any required documentation, turnaround times and fees. Start your application well in advance to allow enough time for processing. Some visas may take many weeks or even months to obtain, depending on the country and time of year.

What should I wear on my Willow Springs holiday?

Do some research into the types of clothing people in Willow Springs wear, and maybe even check out social media fashion pages for inspiration. Try to create a versatile travel wardrobe with pieces that work for your destination and showcase your personal style. Be sure to look at the local weather forecast so you can pack your bags accordingly. The warmest month in Willow Springs is July, with average daytime temperatures of 23ºC. If you plan to travel during the coolest month of January, the mercury averages -4ºC during the day.

What does an Expedia Willow Springs holiday include?

It comes down to what sort of trip you have in mind. Willow Springs travel deals can include hotels, car hires and flights. You can mix and match to create the travel package that suits you. You can also add on experiences and activities after you've booked to score even bigger discounts. Expedia has different kinds of properties, with the most well known in Willow Springs being private holiday homes. With Expedia, you'll always have the freedom to personalise your holiday just how you like it.

Does Expedia offer Book Now, Pay Later Willow Springs holidays?

Expedia has partnered with online lender Klarna to make booking your next break easier on the purse strings. Paying in instalments means you can spread the costs of your next adventure, leaving you with more cash to splash while you're away. Klarna has several payment plans to choose from, so you're sure to find something that suits your budget. Take a look at these flexible payment options:

  • Pay monthly holidays: If paying in multiple transactions is something that would work for you, Klarna can help. Paying in several transactions will make your holiday dreams possible.
  • No-deposit holidays: If not paying upfront for your getaway makes clicking that "book now" button easier, consider a no-deposit holiday plan from Klarna so that you can Book Now, Pay Later!

Can I choose my airline with a Willow Springs Expedia holiday?

Yes, definitely. Expedia has over 400 partner airlines to select from worldwide. With so much choice, finding the right carrier to bring you to Willow Springs shouldn't be hard.

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