Highwood Holidays from £1,017
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- Rest easyPackages with flights are ATOL protected
Your Highwood Holiday
Book a custom holiday package to Highwood and get ready to experience this incredible city how you like. Consider staying in the neighbourhood of Riverwoods, which is good for nature and tons more. A trip to Highwood is an excellent opportunity to take in the sights. Be sure to look around renowned attractions like Chicago Botanic Garden, Lake Forest College and Marriott Theatre. No matter your travel plans or the size of your budget, putting together a tailored Highwood holiday is a breeze with Expedia.
Top Highwood Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
£1,111
per person
3 Nov - 10 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Fantastic breakfast, great location, great room. The rooftop terrace was amazing, but we wishes we had known to make a reservation to be able to enjoy a drink there.
Reviewed on 26 Aug 2026
Swissotel - Chicago
Downtown Chicago
£1,152
per person
3 Nov - 10 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,553 reviews)
Pros: Location is excellent. View was excellent. They upgraded my room from the 4th floor to the 28th floor at no extra cost. Cleaned when I requested.
Cons: Staff was a bit snooty snooty hoity toity. Didn't know I had to pay for parking so that cost more than I budgeted for, it was also an unnecessary hassle to do due to poor internet connection. Confusing amenity fees that I thought I was properly taking advantage of but toward the end felt was taking advantage of me to extract more money. I requested some items be brought up to our room only for staff to tell me I had to come down to the lobby myself to grab them.
Ultimately I can summarize the experience easily as its not worth what I paid for. Also no pool but thats more on me for not checking for that ahead of time.
Reviewed on 26 Aug 2026
Highwood Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Population | 5,400 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 24ºC |
Top Sights | Genesee Theatre, Marriott Theatre and Kohl Childrens Museum |
Top hotels in Highwood
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
£209
18 Sept - 19 Sept
includes taxes & fees
8.4/10 Very good! (2,446 reviews)
"Very convenient, helpful staff"
Reviewed on 26 Aug 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
£149
7 Sept - 8 Sept
includes taxes & fees
9/10 Wonderful! (3,096 reviews)
"Had a great time at the annual FanExpo. The skywalk was convenient but they closed it through the day which totally defeated the purpose. Great time otherwise."
Reviewed on 27 Aug 2026
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd Rosemont IL
Fully refundable
£120
7 Sept - 8 Sept
includes taxes & fees
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.
What to do in Highwood
Chicago: Willis Tower Skydeck and The Ledge Ticket
£35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
£18
per adult
90% of travellers recommend
Frequently asked questions
Why should I book my Highwood holiday with Expedia?
With top-value airfares, hotel and car hire options all in the same place, Expedia makes planning your Highwood getaway hassle-free. What's more, we can help you bundle your bookings into a package holiday so you can save even more. Select from fabulous stays, add your flights and/or a hire car (and maybe even some fun activities!) and score unbeatable prices. Want to change your plans? Expedia has a flexible cancellation policy for many bookings. To discover more, check out our Customer Service Portal link.
When is the best time of year to holiday in Highwood?
If you enjoy the excitement that comes with peak season, visit Highwood in March, May and June. If you'd like a calmer vibe, December, January and February are better times to visit. To get an idea of the type of weather you can experience, the average temperature during the day in January, the coolest time of year in Highwood, is -4ºC. The warmest time here is July, when temperatures average 22ºC.
How do I get a cheap holiday to Highwood?
Bundle your hotels and flights with Expedia to save on your next trip. With over 400 airlines and 321,000 hotel options worldwide, your Highwood holiday can be tailored exactly to suit your budget. With all that extra money, why not add one or more awesome tours and experiences? It's an easy way to unlock even more discounts. That dream holiday to Highwood is closer than you thought! Learn more about how you can save money on your next holiday when you combine your flight and hotel bookings with Expedia.
What should I do on my Highwood holiday?
Offering popular attractions like Chicago Botanic Garden and Lake Forest College, a holiday in Highwood promises lots of fun things to do and see. Northwestern Lake Forest Hospital and The Glen Club are a couple of other sights also worth checking out.
Do I need a visa for my Highwood holiday?
Visa requirements for Highwood vary depending on your nationality and the purpose of your visit. Check official government websites to determine if you need a visa for your trip. Here you'll also find the most up-to-date information, including details about application procedures or supporting documentation you might need. Research your visa requirements in advance to ensure a hassle-free travel experience. Also double-check to see that your passport is valid for at least six months from your planned return date.
What should I wear on my Highwood holiday?
First, consider the sorts of activities you have planned during your Highwood holiday and choose versatile pieces that can be mixed and matched. For fashion inspiration or even information on dress codes, look up style blogs or social media accounts.
What does an Expedia Highwood holiday include?
It depends on what sort of trip you're planning. Highwood holiday deals can include car hires, flights and hotels. You can mix and match to find the bundle that suits your needs. You can also add on activities and experiences after you've booked to score even bigger discounts. We've got a wide range of properties, like private holiday homes, which are the favoured choice in Highwood. Whoever you're taking time off with and whatever you want to do, personalising your escape is a cinch with Expedia.
Does Expedia offer Book Now, Pay Later Highwood holidays?
Your bank balance shouldn't get in the way of escaping on holiday, so Expedia has come up with a solution to help. Now that we've joined forces with online lender Klarna, it's easier than ever to book a fabulous getaway without hurting your hip pocket. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your break. Check out these flexible payment options:
- Pay monthly holidays: Make your holiday dreams a reality sooner with Klarna's manageable instalment plans. If paying across multiple transactions works for you, choose this option at checkout.
- No-deposit holidays: When you want to jump on an incredible deal but your budget doesn't quite go that far, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to secure your getaway.
Can I choose my airline with a Highwood Expedia holiday?
You can, and with over 400 airlines to pick from across the globe, you've got lots of choice. Look through the available options and find out which airline best fits your budget and needs.
* 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.
