Highwood Vacations from NT$42,501

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The Latest Highwood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Downtown Evanston
per person
Oct 8 - Oct 14
found 8 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
7.6/10 Good! (1,007 reviews)
Great place in Evanston. So close to everything.

Reviewed on 2025/7/31

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 8 - Oct 14
found 9 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.4/10 Exceptional! (2,253 reviews)
I loved how smooth the check in process was and all the amenities. Great rooms.

Reviewed on 2025/8/1

The Chicago Hotel Collection - Wrigleyville

The Chicago Hotel Collection - Wrigleyville

3.5 out of 5
Lakeview
per person
Oct 8 - Oct 14
found 8 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
6.8/10 (822 reviews)
The hotel had no on-site staff. We had to call a phone number to get our room key and were put on hold for a long time. The room only had hand soap—shampoo and conditioner had to be picked up from downstairs. The toilet paper roll in our room was already half used. A perk was receiving three free drinks from the bar next door. A nice spot to check out is Cheesy, located right across the street.

Reviewed on 2025/7/31

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
per person
Oct 8 - Oct 14
found 9 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.2/10 Wonderful! (229 reviews)
Room was clean, balcony had a nice view, bed were comfortable, shower was nice

Reviewed on 2025/7/31

Holiday Inn Express Chicago - Magnificent Mile by IHG

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 out of 5
Downtown Chicago
per person
Oct 8 - Oct 14
found 9 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
8.4/10 Very Good! (1,002 reviews)
Excellent attention from the reception area. And excellent and cordial smilling face

Reviewed on 2025/8/1

Find the Best Highwood Vacation Packages

Highwood Hotel Deals

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
Fully refundableReserve now, pay when you stay
The price is NT$4,046 per night from Aug 9 to Aug 10
NT$4,046
NT$4,612 total
Aug 9 - Aug 10
includes taxes & fees
8.6/10 Excellent! (1,805 reviews)
"Excellent exce"

Reviewed on 2025/7/31

Hyatt Regency O'Hare Chicago
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NT$5,373 per night from Aug 23 to Aug 24
NT$5,373
NT$6,307 total
Aug 23 - Aug 24
includes taxes & fees
8/10 Very Good! (2,071 reviews)
US break
"Hotel is well run and organised, very friendly staff and superb facilities. Buffet breakfast excellent with really great staff notably Ali and Mohammed and Emma, aka Da Queen! Really easy access to Metro and onwards to City Centre. Front desk very helpful.Ricardo Delgado sorted out a late check out ..."

Reviewed on 2025/7/30

Hilton Chicago O'Hare Airport
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NT$4,559 per night from Aug 28 to Aug 29
NT$4,559
NT$5,352 total
Aug 28 - Aug 29
includes taxes & fees
8.4/10 Very Good! (1,108 reviews)
"Carluccis and giordano’s was great"

Reviewed on 2025/8/1

Marriott Chicago O'Hare
See all 1,363 properties in Highwood
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.

Discover the most popular places to visit in Highwood

Wrigley Field featuring cbd, a sporting event and a city

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 showing night scenes, a city and signage

Michigan Avenue

You can enjoy some retail therapy 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 featuring a sunset and rides

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Frequently asked questions

How much does a Highwood vacation package cost?
You'll find cheap prices from NT$42,501 on Expedia for your Highwood escape. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Highwood costs.
What are the cheapest months to go to Highwood?
You can generally find lower rates and greater availability in January, February and November. Explore our cheap Highwood vacation packages and you could land some great off-season deals.
How many days is enough for Highwood?
With a well-organized travel plan, you can easily visit the top Highwood attractions in a few days. But if you prefer to discover lesser-known spots or go on day tours, consider booking your Highwood vacation for longer.
How to find the best Highwood package deals?
Bagging a cheap Highwood package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, add some filters and see what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Highwood package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Highwood vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking hotels and flights separately. Better still, you can personalize your Highwood escape to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Highwood?
If you're considering a spur-of-the-moment Highwood getaway, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Highwood?

  1. Pick the right time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to travel to Highwood.
  2. Figure out your budget: Make sure you have enough money to cover everything from dining out and transportation to experiences and flights. Your hotel will probably be the biggest expense during your trip to Highwood.
  3. Decide how long to go away for: Now that you're more familiar with Highwood, you can figure out the right length of your vacation. Pull together a rough itinerary and allocate enough time for all the things you want to do.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to choose a Highwood vacation package that brings all your bookings together.

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