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Highwood Vacations from ￥302,471

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 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

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Highwood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Full-size fridge, microwave, oven, stovetop
    Sep 23 - Sep 27

    Level Chicago – Old Town + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.0/10 - Wonderful (512 reviews)
    Roundtrip • Tokyo (TYO) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥374,077
    ￥302,471
    per traveler
    found 10 hours ago
    Level Chicago – Old Town
  • Smart TV
    Sep 23 - Sep 27

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (545 reviews)
    "Had a lovely stay!"
    Reviewed August 5, 2026
    Roundtrip • Tokyo (TYO) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥389,820
    ￥304,796
    per traveler
    found 10 hours ago
    Level Chicago Fulton Market
  • Terrace/patio
    Sep 23 - Sep 27

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

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (2,641 reviews)
    "Everything was great."
    Reviewed August 4, 2026
    Roundtrip • Tokyo (TYO) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥427,298
    ￥342,162
    per traveler
    found 10 hours ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Indoor wedding
    Sep 23 - Sep 27

    Swissotel - Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.0/10 - Wonderful (3,538 reviews)
    Roundtrip • Tokyo (TYO) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥392,413
    ￥319,187
    per traveler
    found 10 hours ago
    Swissotel - Chicago
  • 2 restaurants; breakfast, lunch, and dinner served
    Sep 23 - Sep 27

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (3,812 reviews)
    Roundtrip • Tokyo (TYO) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥412,403
    ￥335,482
    per traveler
    found 10 hours ago
    LondonHouse Chicago, Curio Collection by Hilton

Highwood Hotel Deals

Lobby

La Quinta Inn & Suites by Wyndham Bannockburn-Deerfield

La Quinta Inn & Suites by Wyndham Bannockburn-Deerfield
3.0 star property
5.9 km from Highwood
9.0 out of 10, Wonderful, (1,012 reviews)
"One of the largest rooms I’ve ever seen! Also had a nice freezer in the compact fridge, for our travel ice packs. Hotel definitely shows its age and needs updates. Our hairdryer did not work. Our phone had no connection, and someone from the front desk came to simply reconnect the cable. We were told that people commonly bring their own game systems or different things in and disconnect their cable. But all of the staff was very friendly. Breakfast was decent. The place also seemed clean,...
The price is ￥15,474
￥17,174 total
includes taxes & fees
Sep 1 - Sep 2
La Quinta Inn & Suites by Wyndham Bannockburn-Deerfield
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.
See all properties in Highwood
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.